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Best Maui luau experience

Maui Sunset Dinner Cruise & Maui Luau

• ONLINE PRICE
• Tour Features
• What to bring
• Food & Drinks

Sunset Cruise Online Price

Price includes more space with limited capacity at 60%, freshly prepared food & open bar. Taxes and fuel surcharge are added to the price.

Call Guest Services at 808.242.0955 for Military, Senior, Kama’aina, Group, and Special Rates.

• OFF SEASON JUNE TO AUGUST
• Adult $ 159 $179 Save $20 $ 179
• Child (6-12Y) $ 99 $119 Save $20 $ 119
• Infants (0-5Y) Free Free

Luau Polynesian Dance & Music

Service & Crew Impeccable Service & Expert Crew

Delicious Food Delectable Sunset Dinner

Open bar Fully Stocked Open Bar with Microbrew Beers, Liquor, Wine & Mai Tais

Destination Maui’s Majestic Coastline

Where to board Maalaea Harbor North Dock (Left of USCG) Directions to Maalaea Harbor

Boarding / check-in Tues, Thurs, Fri, Sat: 5:00 pm

Trip duration Tue, Thurs, Fri, Sat: 5:30 - 7:30 pm

• Reef-Safe   Sunscreen Only
• Hand sanitizer

Picture ID required to consume alcoholic beverages

• Island Fruit Display & Assorted Cheeses w/ Artisan Crackers
• Stir Fry Vegetables
• Coconut Roasted Sweet Potatoes
• Island Style Baby Back Ribs
• Shoyu Chicken
• Assorted Tropical Desserts

• Micro-brewed Beer
• Napa and Central Valley Wines
• Filtered Water
• Tropical Cocktails

Our Open Bar includes micro-brewed beer from local favorite Maui Brewing Company (Bikini Blonde Lager, Big Swell IPA) on tap, Napa and Central Valley red and white wines, tropical cocktails featuring hand-crafted spirits, juices, filtered water, and soda.

• From WAILUKU / KAHULUI
• From LAHAINA
• From KIHEI / WAILEA

Take Hwy 30 (Honoapi’ilani Hwy) and keep going straight until you reach the main intersection for the Maui Ocean Center. Turn left at the lights and pull into the harbor.

Head south on Hwy 30 (Honoapi’ilani Hwy), and as the road opens up after the tunnel, you will see a sign for Maalaea Harbor, followed by Buzz’s Wharf. Turn right at the Maalaea Harbor Sign. If you pass the Maui Ocean Center on your right then you’ve gone too far!

Head north on the Pi’ilani Hwy (Hwy 31), or S. Kihei Rd and follow the signs that take you to Hwy 31. Eventually, that road will end in a T-intersection. Get in the left turn lane to follow the signs pointing to Lahaina. Turn left and get onto Hwy 30 (Honoapi’ilani Hwy). After a few minutes you will see the main intersection for the Maui Ocean Center on your left. Turn left at the lights and pull into the harbor.

Maui sunset cruise

Watch the Maui Sunset while enjoying fresh food, open bar, and a Maui luau!

Napoʻo ʻana o ka lā is how to say “sunset” in Hawaiian.

Our Maui Sunset Dinner Cruise and Maui Luau is a unique opportunity to experience local culture expressed through Polynesian dance, song, chant, and storytelling. Live entertainment is headlined by local Hawaiian guitarist Kekoa, who has performed for over 30 years throughout the Hawaiian Islands and the world. Relax to his Hawaiian slack key as Naia and Ola share traditional hula and Polynesian dance.

We cherish traditional story and dance, as our genuine expression of aloha spirit and Hawaiian culture. Experience the spirit of Hawaii and Polynesia in a close, intimate setting, operating at 60% of our USCG capacity. Our Maui Sunset Dinner Cruise & Maui Luau is unforgettable, featuring breathtaking views, freshly prepared island inspired food, premium open bar, hula, and Hawaiian music.

Relax and enjoy spectacular views of the Hawaiian sunset, with delicious, freshly prepared food, and premium open bar. Our premium bar features wines from Napa, local micro brewed beer, and top shelf spirits. Watch authentic Polynesian dancers put on an entertaining and interactive performance. During the winter months, you’ll even enjoy Maui’s best whale watching !*

To ensure that your experience is comfortable and fun, we limit our guest seating to 60% our Coast Guard-approved capacity.

*Whale watching season is typically from January through March.

What you can expect

Polynesian Dancers

Hula dancers telling a story through mesmerizing movements

Delicious food

Our freshly prepared luau feast offers something for everyone

TWO HOURS AT SEA

A fun, laid back experience like no other

Open bar with microbrew beers, blended drinks & cocktails

STUNNING VIEWS

360° panoramic view of Maui coastline & Mt. Haleakala

Attentive Crew

We go above and beyond to make sure your experience is the best

Whale Watching

Incredible whale watching views from January-March every year

Freshly prepared food

• Assorted Cheeses w/ Artisan Crackers

Guests aboard the Pride of Maui can move throughout the boat and mingle while enjoying a variety of freshly prepared, premium chef-inspired dishes.

Enjoy delicious island-style baby back ribs and shoyu chicken. Make sure to save room for our delicious Hawaiian-style desserts!

• Liquor List
• Mixed Drinks

Micro-brewed Maui Brewing Company local beers

• Bikini Blonde
• Big Swell IPA

• Trader Vics Silver Rum
• Trader Vics Dark Rum
• Bacardi Silver Rum
• Redemption Bourbon
• New Amsterdam Gin
• John Barr Whisky
• Durango Tequila
• Riazul Tequila
• New Amsterdam Vodka
• Michaels Celtic Irish Cream
• Blue Curacao

2 red and 2 white wines including (Labels vary):

• Piña Coladas
• Bloody Mary

Live entertainment

• Polynesian dancers

Experiencing live hula, up close and personal, watching a sunset performance off the coast of Maui is unsurpassed. Polynesian dance tells historical and mythological stories through graceful movement of the eyes, hips, and legs, where the hands complete the story.

Why choose us?

• All-Inclusive

Picture yourself watching a beautiful Maui sunset aboard Maui’s Best Sunset Cruise, relaxed on calm Pacific Ocean waters, where you will enjoy cultural emersion with dancing, entertainment, a chef-created dinner menu, and an open bar. See Maui’s gorgeous coastline, the West Maui Mountain range, Mt. Haleakala, and the outer islands of Kahoolawe, Hawaii, Lanai, and Molokai in the distance. Our Maui Sunset Dinner Cruise & Maui Luau is an exceptional value and one of the most sought-after activities in the Hawaiian Islands.

Our limited seating at 60% of our USCG capacity provides greater space and more comfort to safely roam throughout the vessel.

Known for its stability, Pride of Maui is the largest maxi-power catamaran on Maui. You will have plenty of room to comfortably move around the catamaran during your Maui sunset luau cruise. Raise a toast as the sun slowly sets into the sea. You have the best seat on the ocean to take it all in.

Aboard the Pride of Maui Sunset Dinner Cruise, you will enjoy Hawaiian entertainment, an open bar, and freshly prepared Hawaiian-style cuisine. We are proud to offer a wide range of features to create lifelong memories while you luxuriate in the panoramic views of Maui’s one-of-a-kind sunset.

Let the beautiful Maui Sunset, our unique amenities, expert crew, and relaxed atmosphere make memories that last a lifetime. Discover the perfect end to your day with a Maui sunset dinner cruise aboard the one and only Pride of Maui.

Observation deck

Our sprawling observation deck offers a 360-degree unobstructed view of the coast to ensure extraordinary photo opportunities. With over 2500 ft. of open deck space, and by limiting our capacity to just 60%, you’ll have extra room to roam, relax, and reflect.

You must experience a spectacular Maui sunset aboard the Pride of Maui’s Sunset Dinner Cruise.

Questions about the tour?

How crowded are the tours usually.

Even though the spacious Pride of Maui is Coast Guard Certified for 149 passengers, our trips operate at 60% capacity to ensure your experience is the absolute best.

What time is check-in for the Sunset Dinner Cruise?

*October 1st thru February 28th* Check-in time: 4:30 pm.

*March 1st thru September 30th* Check-in time: 5:00 pm.

How long does the Sunset Dinner Cruise trip last?

*October 1st thru February 28th* Departure time: 5:00 pm, Return time: 7:00 pm.

*March 1st thru September 30th* Departure time: 5:30 pm, Return time: 7:30 pm.

What do you serve for dinner on the Sunset Dinner Cruise?

Our Sunset Dinner Cruise cuisine is superb. For appetizers, enjoy assorted cheeses with artisanal crackers and Maui onion tartlets. Savor island-style baby back ribs, shoyu chicken, coconut roasted sweet potatoes, stir-fry vegetables, Maui gold pineapple slaw, assorted tropical desserts, and taro rolls for dinner.

Will I become seasick?

At 65 feet in length and a beam (width) over 30 feet, our very large (Maui’s largest), multi-hulled maxi-power catamaran offers unsurpassed stability and comfort. Very few of our guests become ill, even those prone to motion sickness. If you are in doubt, there are products available over the counter at our local Longs Drug stores to ease your mind. Just ask the pharmacist for one of many preventative options. If you are susceptible to motion sickness, Pride of Maui is positively the right vessel for you! She is famous for her fantastic stability.

Do you cancel during bad weather for the Sunset Dinner Cruise?

The weather here is referred to as “micro-climates.” It can be raining hard where you are, yet sunny and calm at the harbor and our destinations. The weather forecast comes out of Honolulu and is frequently inaccurate for Maui. We have frequent passing showers that turn to clear skies in short order. With more than 30 years in the business, we are your best resource for the weather. Our Captains are seasoned veterans with extensive local knowledge. If we have not called you, please show up at the harbor with expectations to go out, even if it is raining or windy. If the conditions are unsafe to operate, you will be given the option to reschedule or cancel with a full refund. All of our destinations are weather permitting. We will take you where the conditions are the best overall, for a safe and enjoyable experience. Pride of Maui is the largest and most stable power catamaran on Maui.

Can we come aboard if pregnant?

We accommodate pregnant guests regularly. Please ask your doctor if it is safe for you to be on a boat during your pregnancy. Our vessels are large and stable, although each pregnancy is different and your doctor knows you best.

Can we bring a stroller on board?

Absolutely, they make a convenient base to operate out of for families with toddlers and infants. The Pride of Maui is very spacious, easily accommodating strollers.

Will we need money on the boat?

A little cash ($20-$40) on-hand is a good idea.

Do you have lockers on board?

We have storage below the outer perimeter bench seats. Many of our guests bring a backpack or soft bag to keep their personal items in. There are up to 9 crew on the boat daily and in the 30 plus years we have been operating, none of our guests have reported a loss.

What should we bring?

Payment methods such as credit card, cash or traveler’s checks.

Is there parking at the harbor and how much does it cost?

The parking is operated by Diamond Parking Services. The lot closest to our slip has a machine that only takes cash (No change is given). You can also pay with a credit card by phone by dialing in or using a QR code. The cost of parking is $3.

How do we find your location?

The address to key into your GPS is 101 Maalaea Road, Maalaea, Maui, Hawaii. We are located in the central part of the island, off Highway 30. The entrance to Maalaea Harbor is below the Maui Ocean Center. Once you enter Maalaea Harbor, proceed to the ocean side of the harbor (opposite the Coast Guard station), to the public loading dock, where we check you in.

Does it cost extra for alcoholic beverages?

Our sunset dinner cruise features an open bar at no additional cost to our guests!

The crew is simply fantastic

The most authentic people around, a good way to have a great evening.

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Maui Sunset Cruises and Catamaran Tours

Book your sunset catamaran cruise on maui today.

Hawaii offers one of the best island adventures in the world, and you can get more of it by experiencing it through a Maui sunset cruise and Catamaran Tours! You will surely love the front row seat of Maui’s magnificent sunsets. Enjoy it more with handcrafted cocktails and seafood cuisine prepared just for you. The splendid Hawaiian sunset will bring awe and will surely be one core memory you can share with your loved ones and friends.

During the tour, marvel over the beauty of the nearby islands of Molokai, Lanai, and Kahoolawe. While at the water, look for dolphins as they swim and jump offshore while enjoying unlimited drinks from a premium bar and refreshments. These Maui sunset cruises and Catamaran tours will be the perfect way to end a day on the island.

At Sea Maui, we know that Hawaii is a major destination for relaxation and fun times. That is why we offer a Maui sunset dinner cruise! This will allow you to loosen up and enjoy yourself while marveling at the wondrous Maui sea. You can dance to live music on board and sip on two free drinks from a full bar. Travel by boat and see the sights illuminated at night. Our guests can also choose from various dinner options prepared by our experienced and talented chef. Make it more amazing by picking from multiple cruise times to fit your schedule.  

Sea Maui Sunset Cruise and Catamaran Tours

Sea Maui Sunset Cruise tour packages offer options that can fit your style and budget. You can pick slots that will suit your time, and we will ensure every second of your tour is worth it. Here are the three Sea Maui sunset cruise options that you can choose from:

• Calendar First Friday of Every Month
• Hour Glass 2.5 hours

‘Ike Maui Sunset Dinner Sail

Indulge in the extraordinary ‘Ike Maui Sunset Dinner Sail, set against the stunning backdrop of Ka’anapali & Lahaina. Join us for an unforgettable evening as we honor the rich heritage of Hawai’i and delve into its captivating culture through mele (music) and hula.

• Calendar Daily , Includes Live Music on Wednesdays and Saturdays!
• Hour Glass Approx 2.5 hours

Premium Maui Sunset Cruise with Dinner

Are you looking for a unique dining experience to leave behind the hustle and bustle of the land? Sea Maui’s Sunset Dinner Sail is our premium dining and sailing experience.

• Most Popular!
• Calendar Daily , Includes Live Music on Tuesday & Thursday!
• Hour Glass Approx 2 hours

Original Sunset Cocktail Cruise on Maui

Experience Sea Maui’s classic sunset charter as we depart from Ka’anapali Beach to enjoy a beautiful Hawaiian sunset with handcrafted cocktails in hand.

Premium Sunset Cruise with Dinner Tour on Maui

Sea Maui’s Sunset Dinner Sail is our premium dining and sailing experience. Leave the rush and bustle of land behind as we welcome you on board our newest vessel. The stunning Sea Maui III is a 65-foot luxury catamaran recently renovated. Feel the flow of the ocean beneath you as you sail with the tradewinds down Maui’s shore. Take in the majestic sunset views of Maui and its neighboring islands. Drink exquisitely handcrafted beverages and quality beers from the spacious cabin for a memorable dining experience. This cruise also includes a splendid dinner made by Cafe Jai’s. It is a specifically designed buffet-style menu just for you. Find out more about the inclusions of the Premium Sunset Cruise here .

Original Sunset Cocktail Cruise

One of the Ka’anapali classics is Sea Maui’s Original Sunset Cocktail cruise where you can witness the picturesque and breathtaking view of Maui’s sea sunsets. You shall get the best view of the spectacular pastel sunset colors as they change and extend across the horizon and slowly dissolve into the waters of Hawaii.

During the winter, Sea Maui’s Sunset Cruise also participates in some Maui whale watching! Nothing more incredible than spotting majestic humpback whales as the sun sets over the Pacific.

You can expect to take in stunning panoramic views of Molokai, Lanai, Maui, and Kahoolawe. Make sure your cameras are on the go because there will be amazing photo moments during the cruise! You can also savor the pupus meals prepared and served by Cafe Jai. As we sail across the calm seas, there will be handcrafted cocktails from our premium bar and local Maui breweries. With a drink in hand, everything in Maui is more enjoyable! 

Sunset Live Music Cruise

Sea Maui’s Sunset Live is created for guests looking for more excitement while on the water. Every Sunset Live is transformed into an absolutely unique event. The guests will be entertained by musicians, who are well-known local artists who play exclusively for the audience on board.

Aside from the live music and entertainment, you can also sip through amazing handcrafted cocktails and delectable food to liven up your evening. Finally, enjoy the magnificence of the pastel sky as the sun sets over the Pacific! The perfect way to unwind and end your day on Maui.

Sea Maui’s Sunset Cruise and Tours

Sea Maui started back in 2015 as the new guys on shore. Despite being a newbie in the field, we are not new to sailing in Hawaii. Many of our crew started working on boats on Waikiki Beach.

Over the years, Sea Maui has worked out to become a staple in Ka’anapali Beach. We make sure our guests get the best time and the magical experience Hawaii has to offer to its tourists. In addition, all the crew members are experienced, certified, and skilled sailors, working together in harmony to give you the best possible experience. 

Since Maui is home to some of the most incredible sunsets on the planet, we put together our Maui sunset cruise and Catamaran tours , so everyone can experience Maui’s beauty on another level. You can witness the grand sunset of the Pacific while having some crafted drinks and food catered by our partner and trusted Cafe Jai. You can also see the magnificent sea creatures of Hawaii with the open-air layout of the cruise. A 360-degree view of the open sea with the seasonal appearance of whales and dolphins as live music plays in the background. Sea Maui’s famous sunset sail options are simply the best evening tours Ka’anapali has to offer.

Sea Maui is more than just Maui sunset cruise and Catamaran tours , and your trusted Maui adventure buddy, we make sure that every moment with us is comfortable and memorable. Get to know more about the adventures you can enjoy while in Maui and get in touch with us here !

More About Sea Maui Sunset Trips

• Chevron down More Information:
• Easy-to-find check-in location at The Whaler’s Village Shopping Center and the only boat with a physical location/booth on the beach. Our “Ocean Activities” booth is located along the beach walk at Whaler’s Village between Leilani’s restaurant and The Westin Resort.
• The only boat with free parking validation, savings of $20 or more!
• Exceptional staff & service/certified naturalists for whale watches (seasonal)
• All crew members are lifeguard and CPR-certified.
• Food prepared by Cafe Jai. Can easily accommodate food allergies or dietary restrictions with 24-hour notice.
• Premium open bar on all trips.
• Complimentary juice, water, Coke, Diet Coke, Sprite, and lemonade on all sails.
• Kama’aina rate available with Hawaii ID, please call  (808) SEA-MAUI  to book.
• Private charters also available.

8 Best Maui Sunset Cruises For a Great Night Out

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I’ve traveled all over the world and one of the things I always look forward to doing in every location is watching the sunset (and now that I have young kids I’m usually also watching the sunrise ). 

While we’ve seen some great sunsets, none compare to Maui. The sunsets here are unbelievably spectacular. Pink, purple, ombre skies that sometimes you can’t even believe are real. And while you can certainly see these sunsets from land, there’s something very special about enjoying them from the water. 

If you’re looking for a Maui sunset cruise that really wows, we have a list of the best of the best, and what makes each one so special. Living on Maui for three years we were able to experience more than our fair share of these, so we’re happy to be able to share our advice with you!

Want to get right to it without reading all the details? Jump in and book these recommended tours: 1. This is the cruise to book if you want live music 2. Book this for a convenient Wailea departure 3. Getaway from the crowds with this small group sail 4. Luau or cruise? Get both with this sunset luau cruise 5. Enjoy a full dinner cruise with your sunset 6. This is our favorite tour during whale season Need more time on (and in) the water? Make sure you check out our top snorkeling tours on Maui .

1. Sunset Live Music Cruise (Ka’anapali)

Head out onto the water with a drink in hand while being serenaded by an on-bard musician. This sunset live music cruise really knows how to have a good time. Offered every Tuesday and Thursday, you and approximately 47 other guests will board a 55’ catamaran for two hours of fun. 

Included is live music, an open bar (beer, wine, champagne, and mixed drinks), and pupus (light appetizers). 

They depart from Ka’anapali beach (how convenient!) and if you’re not staying in Ka’anapali you’ll get a 4 hour Whalers Village parking validation. Note that because of the convenient location and not needing to drive to a harbor, they do beach loading. That means you’ll be wading into the water up to your knees in order to board. Long dresses and pants aren’t ideal here. 

If you’re not interested in live music, or you can’t go on Tuesday or Thursday, they offer a regular sunset cruise (sans live music) all other days of the week. Learn more about their standard Ka’anapali sunset cocktail cruise .

2. Sunset Luau Cruise (Ma’alaea Harbor)

Can’t decide between going to a luau or enjoying a sunset cruise for an evening activity? Do both with this sunset luau cruise ! While this isn’t a true full luau, you’ll still get to experience traditional music and dance with Maui’s gorgeous sunset as a backdrop. 

You’ll board the maxi powered catamaran which leaves from Ma’alaea Harbor in central Maui (paid parking available). On board you’ll be treated to appetizers, a full dinner, and an open bar with beer, wine, and mixed drinks. During the cruise you’ll have the opportunity to enjoy Polynesian dance, which makes this experience part sunset cruise, part luau. 

The boat has a coast guard approved occupancy of 149 people, but they intentionally limit it to 60% of capacity so there’s extra space to stretch out. While this is the most expensive cruise on this list, you do get to see hula and a full dinner.

If you prefer to keep your luau and your sunset sail separate, we have a list of the best luaus on Maui.

3. Catamaran Sunset Sail

Spend 2.5 hours aboard this 48 passenger, 65’ catamaran, with plenty of room to spread out. Excited for a little more adventure? Head up front to the trampolines (though you might get a bit wet). 

They have two different boat options, both leaving from Lahaina Harbor. The first is on a 65’ Catamaran, with capacity up to 48 passengers. The second cruise on the Paragon is limited to 25 passengers. 

On both, you can enjoy pupus as well as an open bar with cocktails, wine, and beer. 

Note: Due to the damage to Lahaina Harbor during the fires, Sail Maui is no longer operating from Lahaina Harbor. Book their Molokini Snorkel Tour from Ma’alaea Harbor in Central Maui to support their crew!

4. Adventure Sunset Sail

Staying in Wailea or Kihei? This is the sunset cruise you want to be on. This Adventure Sunset Sail departs from Maluaka Beach , a very convenient South Maui location. The adventure part of this sunset sail is that you get to enjoy a beach loading, which means you should expect to get wet! We happened to go out on an evening when the south swell was particularly large, so we were in for even more of an adventure! (You can see the video of our experience below). 

Once aboard the 65’ catamaran, you’ll enjoy two hours of sail time, 3 appetizer courses from The Market Maui (a great Wailea deli/restaurant), and an open bar featuring local brand like MauiWine and Ocean Vodka. 

If you haven’t rented a car or you don’t want to drive, they do offer shuttle service from Wailea hotels. But book early as this option tends to fill up! 

We loved this sunset cruise experience and we were able to go out for a great night in Wailea after it ended. Here’s a list of our favorite Wailea restaurants .

5. Lahaina, Ka’anapali, or Ma’alaea Sunset Sail

Another stellar option is this 2 hour sunset cruise which departs from three different locations on the island: Lahaina Harbor, Ma’alaea Harbor, or Ka’anapali (beach loading). 

A standout feature here is that they offer private tables for two, which makes this a great option for a romantic evening on the sea. They serve plated appetizers and there is a premium open bar with beer, wine, and cocktails. 

If you’ve taken the cruise from Lahaina Harbor, it’s just a short walk to their family-owned pizza restaurant, Kapena’s , which we highly recommend!

6. Champagne Sunset Sail

If you’re looking for a smaller group, this is the sunset sail for you. This is a sailing experience, not just a sunset cruise on their Santa Cruz 50 sailing yacht. With a capacity of only 22 people, this is a fun small group experience. 

While you won’t find as much food on this sail as you will on the others, you’ll enjoy champagne and chocolate. Guests must be 13 years or older to enjoy this experience. 

7. Premium Sunset Dinner Cruise

If you’re looking for something more than a cocktail and pupu cruise, consider a dinner cruise . Hop aboard this 65’ luxury catamaran for 2.5 hours, relax, and enjoy the spectacular scenery and service. 

You’ll depart from the beach in Ka’anapali — very convenient if you’re staying in Ka’anapali. But if you’re not, don’t worry! They give you a 4 hour parking validation for Whalers Village . Once aboard, you’ll have an open bar and a buffet dinner to enjoy. There’s something for nearly everyone when it comes to the food selection. 

Kids of all ages are welcome. But don’t wear long dresses or pants. This is a beach loading boat, which means you’ll get a bit wet while getting on and off. The convenience of this beach loading cruise can’t be beat. 

8. Luxury Sunset Sail from Ma’alaea Harbor (10% off!)

Keep it simple and luxurious with this 2 hour sunset sail. This is arguably one of the best sunset sails for spotting whales in the winter as you’ll cruise through the ‘Au’Au channel. This is the area between Lana’i and West Maui and its warm, shallow waters are a favorite of humpback whales and their calfs!

An open bar and appetizers are included in the price. While this isn’t a small tour (it welcomes up to 48 passengers), it’s a great option for families with small children because kids under 3 sail for free! Plus you’ll save 10% with our discount code!

Maui Sunset Cruise FAQs

Can you see whales on a maui sunset cruise.

You sure can! While these aren’t whale watching tours, if they come across a whale during whale season, they will absolutely stop to watch them. Whale season runs December – April , and these sunset cruises all cruise in prime whale watching locations. So the odds of seeing whales during your cruise is pretty good! 

What is the best place to watch the sunset on Maui?

Head to West or South Maui for spectacular sunset views. You’ll get amazing views both from land or from sea. What we love about a sunset cruise is that you not only get to appreciate the sunset over the water, you get to see the island lit up in the glow of the setting sun. 

What do you wear on a Maui sunset cruise?

Pretty much anything you want! Bring a light jacket or sweater, especially during the winter if you tend to get cold in the evening. There is usually a light wind and after a day of fun in the sun, it can feel a little cool. 

If you’re doing one of the beach loading tours, don’t wear long dresses or pants. Expect that your knees and below will get wet. But that’s part of the adventure of beach loading!

How long is a sunset sail on Maui?

Most sunset sails on Maui are two hours, though you will find some that run a bit longer, at 2.5 hours. But they are quick tours that will usually get you back in time for any dinner plans you have that evening.

Find a great place to stay on Maui: The 7 Best Vacation Rentals in Wailea and Makena The 12 Best Maui Beach Hotels (+ 5 awesome beachfront condos) Where to Stay in Hana Maui for One Night: 4 Great Options

There’s More to See Than Sunsets

Maui is a dream destination and there is so much to see and do. If you want to make your trip planning easy, our itineraries are here to help . With carefully thought-out excursion days, we take you around the island, seeing the best sights, stopping at the best beaches, and eating at the best restaurants. We’ve done the homework for you, now you get to download and enjoy!

My twin sister and I just returned from an amazing birthday in Maui.  I ordered your itinerary for Maui and we relied on it heavily. I just wanted you to know your itinerary was spot on and your recommendations were the best. Thank you so so much. Kate R.

Maui Wayfinder Itinerary

Get the maui itinerary.

The step-by-step itinerary takes you to all the best beaches, snorkeling spots, restaurants, and sights. You’ll get six carefully planned excursion days to help you see the can’t miss stops no matter how limited your time is.

Get all the details on our itinerary and download it for a memorable and easily planned trip to Maui.

I'm the co-founder, with my husband Jordan, of The Hawaii Vacation Guide. We have lived on Maui and Oahu and continue to travel, experience, and learn about the Hawaiian Islands. We travel with our kids, Henry and Edith. I am a planner! I love to plan trips from the mainland and island-hopping adventures, excursion days, and everything in-between. I spend a lot of my time in Hawai'i on a SUP and my favorite time of year in Hawai'i is whale season!

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Don’t start planning without our cheat sheets

You’ll get:

• 4 can’t-miss activities on each island,
• a map with the main sights in town,
• and famous local grindz (eats)!

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CAPTAIN'S SUNSET

Dinner sail.

FIRST-CLASS DINING

Guest dine on a chef-prepared gourmet 4-course dinner at intimate two-top tables seated on deck. The courses are fixed with exception to your entree, which you must select when booking. We do not offer vegan/veg appetizers. 

Ala’e Sea Salt Breadsticks with lilikoi butter

Smoked Salmon on Crispy Pita with fresh dill

Cucumber Cup with Maui Onion Cream Cheese

Tataki-Style Beef Tenderloin Crostini

Caesar Salad with Blue Cheese Vinaigrette

ENTREE OPTIONS (ONE PER GUEST)

Seared Top Sirloin Steak with herb & garlic crust

Fire-Grilled Chicken with citrus & thyme

Fresh Island Fish, panko-crusted with lemon caper butter

Pasta Primavera with Portobello mushroom & sauteed vegetables in fresh marinara with basil

DESSERT TRIO

Lilikoi Cheesecake

Fresh Island Fruit

Dark Chocolate Truffle

DRINKS & COCKTAILS

Feel the aloha vibes as our Crew serve up a wide variety of alcoholic and non-alcoholic beverages–a little tasty something for everyone on this Dinner Sail.

PREMIUM BAR

Maui Brew Co. -Sunshine Girl Golden Ale

Maui Brew Co. -Seasonal Seltzer

Matua Sauvignon Blanc

Josh Pinot Noir

La Marca Prosecco

Captain’s Mule –  Our thirst-quenching twist on the classic Moscow Mule… New Amsterdam Vodka, splash of soda mixed with Elixir G ginger syrup and lime.*Option to sub Vodka for Tequila or Bourbon

Lana’i Tai –  A Mai Tai done the Trilogy way – Mango Rum, Orgeat, Fresh lime, Elixir G ginger syrup, pineapple juice and a float of Potter’s Dark Rum.

Good Ol’ Fashioned – Redemption Bourbon, agave syrup, splash of water, Watkins bitters.

Lahaina Sunrise – Camarena Reposado Tequila, Ginger ale, POG juice, splash of Elixir G ginger syrup and lime.

808 Margarita – Camarena Reposado Tequila, agave syrup, pineapple juice and a dash of bitters.  (808 is the area code encompassing Hawaii.)

*NOTE: Guests must be 21+ to enjoy our bar beverages.

DEPARTURE TIMES

• Feb 1 – April 14 | 5:00pm – 7:30pm
• April 15 – Aug 31 | 5:30pm – 8:00pm
• Sept 1 – Oct 14 | 5:00pm – 7:30pm
• Oct 15 – Jan 31 | 4:30pm – 7pm

Check-in time is 15 minutes prior to scheduled departure time, at the loading dock.

TOUR DURATION

• Approximately 2.5 hours

DEPARTURE LOCATIONS

• Ma’alaea Harbor | Wednesday, Friday, Sunday

The dinner sail departs from slip #62 at Ma’alaea Harbor on Wednesdays, Fridays, and Sundays . Slip #62 is located on the break-wall (ocean) side of the harbor.

The dinner sail departing from Lahaina Harbor is temporarily suspended due to the Lahaina Fires. 

MA’ALAEA PARKING

• 11 Ma’alaea Harbor Rd
• Wailuku, HI 96793

Parking is available within Ma’alaea Harbor for $1 per hr. Please pay via the digital parking kiosks (QR Code) for parking prior to checking in. Trilogy is not responsible for cars that are towed due to a parking error.

WHAT'S INCLUDED

Chef prepared & plated 4-course Dinner with Appetizers, Salad, Entree & Dessert

21+ yrs: Premium Bar

Sodas, Filtered Water, Juices, Mocktails

Sailing & Stargazing (post sunset)

Whale watching (Dec-April)

NOTE: This tour is only available for guests 18 and over

Vegan, Vegetarian, and GF options available. Please make a note in your reservation at check-out

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LANA'I

MA'ALAEA

Sunset sail.

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FROM MA'ALAEA HARBOR: MAUI SUNSET DINNER CRUISE ABOARD THE CALYPSO

Quick Details

• Calendar Availability: Runs Daily
• Clock Mandatory Check-In: 5:00 PM
• Clock Prompt Departure: 5:30 PM
• Clock Duration: 2 Hours
• Users Ages: All ages
• User Small Child: Ages 3 and under free - 1 free child per paying adult
• Map Marker Meet At: Ma'alaea Harbor, Slip 76, 101 Ma'alaea Road, Wailuku, HI 96793
• Anchor Waiver: Please sign the Liability Waiver before you go
• Phone Tour Not Available?: If your dates aren’t available online, please contact us at 808-442-3267
• Info Includes: Dinner & Two Drinks

ENJOY A SUNSET DINNER CRUISE IN MAUI! 

This stable, comfortable, triple-deck catamaran leaves from centrally-located Ma’alaea Harbor. Come aboard this relaxing two-hour excursion, which gives you time to enjoy a delicious meal, explore the incredible craft, listen to great island-style music, and watch the sun go down from your place on top of the waves! Seating on the Calypso sunset dinner cruise in Maui comfortably accommodates any size group, including couples, families, and even large corporate events. You’ll find tables for two, four, eight, and ten, as well as enclaves throughout the vessel to sit and sip drinks, see the ocean from a new perspective, or hang with the kids when they need to fidget.

Explore all three decks, and take your time to find just the right spot in sun or shade. Calypso’s three restrooms are on the lowest deck. The front of the boat is the most open to sun and wind, so wear a secure hat and, as one of our lighthearted guests advised, “consider leaving your fake eyelashes on shore”! After you’ve settled in, pick up a fizzy soda, tropical juice or island themed adult beverage. Your Calypso sunset dinner cruise includes two free drinks, and once the catamaran has motored out of the harbor, you can order alcohol. Friendly crew members tend the bar, and they can bring you Mai-Tais, blended drinks, wine and beer.

When it’s time for the delicious main meal enjoy  juicy prime rib. Mahi mahi, teriyaki chicken, steamed vegetables, roasted potatoes, and chocolate cake is also ready for you to eat. While you chow down, the crew comes by often to take things out of your way, ensuring that no trash ends up in the ocean. There is plenty of time to gaze at the islands of Kaho’olawe and Lana’i in the distance – not to mention the epic snorkeling site, Molokini Crater. Closer to the boat, you’ll see the Kahalawai Mountains of west Maui as they stretch toward the sky. When humpback whales are visiting the islands from Alaska, chances are excellent that you will see some of the magnificent marine mammals on your Calypso dinner cruise! Any time you do, the captain and crew are sure to get on the mic for some whale conversation. You and your group will love this fun time on the sea, so follow the sun, love your loved ones, and have a great meal on the Calypso dinner cruise!

• Chevron down Mandatory Check-In

30-minutes prior to departure

• Chevron down Duration
• Chevron down Meet At

Ma’alaea Harbor, Slip 76, 101 Ma’alaea Road, Wailuku, HI 96793

• Chevron down Paid Parking
• There is paid parking available at Maui Harbor Shops / Maui Ocean Center located at 300 Ma’alaea Road, Wailuku, HI 96793 and at the Ma’alaea Harbor around the boat slips
• Give yourself extra time to account for traffic, weather, road construction, parking , and the walk from the parking lot to the boat slip (10-15 minutes) in order to arrive at check-in 30-minutes prior to departure
• Chevron down Dinner Menu
• Caesar salad with homemade buttery croutons, freshly grated parmesan cheese, and warm breadsticks

Choice of Entrée

• Garlic rosemary roasted prime rib
• Fresh island fish with lemon butter caper sauce
• BBQ roasted chicken thigh and leg combo
• Kiawe smoked baby back ribs
• Penne pasta with Thai basil marinara (vegetarian option)
• All entrees served with white rice and locally sourced sautéed vegetables
• Double-layer chocolate cake and New York style cheesecake
• Chevron down Drink Menu
• Honolulu Beerworks El Guapo Blonde Ale, Hope Island IPA, Kewalo’s Cream Ale
• Mahina Premium Dark and Light Rum, Torado Silver Tequila, Early Times Kentucky Whisky, Nikolai Premium Vodka, Mr. and Ms. Tea Pina Colada
• Sycamore Lane Cellars Chardonnay and Cabernet Sauvignon
• Unlimited ice-cold soda, juice, and water
• Chevron down What's Included
• Live island-style music (most nights)
• Two complimentary alcoholic beverages included, $5.00 each thereafter. Must be 21+ with a valid photo ID
• Unlimited Ice-cold soda, juice, and water
• Triple-deck catamaran with incredible panoramic views
• Comfortable table and chair seating
• Large stable decks with plenty of space to move around
• Experienced and professional captain and crew
• Chevron down What's Available
• Adult beverages are available for purchase $5.00 each
• Dramamine is available for purchase 2 for $5.00
• T-shirts are available for purchase $20.00 each
• Chevron down What's Excluded
• Hotel pick-up and drop-off
• Parking fees
• Chevron down What to Bring
• Light jacket or sweater
• Valid ID required for passengers 21+ who will be drinking alcoholic beverages
• Cash if you plan to tip the crew
• Chevron down What You Should Know
• If you have a dietary restriction (vegetarian, gluten free, etc.) this must be noted and specific dietary restricted lunch requested at time of booking
• There is no meal provided for small child 0 – 3 years old. Someone in your party can share their meal with the small child or you can purchase a child ticket that comes with a meal included
• Minimum drinking age is 21
• Must have valid photo ID
• Operates in most weather conditions, please dress appropriately
• A 24-hour notice is required for cancellation or reschedule
• Children must be accompanied by an adult
• Chevron down Accessibility
• Not wheelchair accessible
• Stroller accessible
• Near public transportation

RELATED CRUISES

• DEC - APRIL

From Ma'alaea Harbor: Maui Whale Watch Cruise Aboard the Calypso

The two-hour Calypso whale watching in Maui is one of the most thrilling family-friendly Hawaiian activities! From December 18th through April 15th, climb aboard our boat, and make your way to the top. Book your Maalaea whale watching excursion online today!

• Hour Glass 2 hours

From Ma’alaea Harbor: Thanksgiving Dinner Cruise Aboard the Calypso

Enjoy the spectacular views of the West Maui Mountains and neighboring islands on Molokai and Lanai as our crew serves you table-side a Hawaiian-influenced Thanksgiving day feast with all the fixings!

• No menu assigned!

Makena Sunset Sail

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Featuring live Hawaiian music, sparkling rosé toasts, marvelous sunset views, and a south Maui direct beach departure, Maluaka’s acclaimed Adventure Sunset Sail is offered weekly for Maui residents and guests alike. Choose from island-inspired menu items and locally sourced spirits and adult beverages, and cruise in style aboard a spacious catamaran, perfect for experiencing a relaxing night on the Pacific Ocean. Space is limited, so book ahead for the best results.

Are you staying in another part of Maui?  Check out this Maʻalaea Dinner Cruise or Maʻalaea Sunset Tour .

BOOK NOW • MORE INFO

• Reviews (9)

More about this activity

With direct views of the stunning Maui sunset, as well as Molokini Crater, the neighbor island of Kahoʻolawe, Haleakala Volcano, and the white sand beaches and turquoise waters of Makena, this tour is an excellent way to spend a romantic outing with a loved one, a fun evening experience with friends, or night out with the girls. Featuring live ukulele styling from local musician Dwight Quenga, you may also get lucky enough to spot local marine life such as Hawaiian Spinner Dolphins, Hawaiian Green Sea Turtles, humpback whales, and more.

Featuring menu items from Wailea’s ‘The Market Maui,’ feast on items like baked pasta, grilled ribeye, seared ahi with chimichurri, salad, vegetarian chickpea salad, cheese and charcuterie plates, hummus and vegetables, and dessert items like brownies, chocolate chip cookies, and toasted coconut. Choose from beverages such as juice and sodas, or complimentary alcoholic beverages with locally-sourced items like Ocean Vodka, Kula Rum, MauiWine, Kona beer, and more.

Toast to the evening’s festivities with a glass of Lokelani Sparkling Ros é, and enjoy the ultra-luxurious catamaran, friendly service, and convenient check-in with your toes in the sand. Shuttle service from popular Wailea Resorts is offered at a minimal fee when enquired about ahead of time, and infants under 2 years of age are free. Whether you’re celebrating a night out with a loved one, a family-fun day, or an exciting excursion with friends, you’re sure to fall in love with this ultra-memorable Maui ocean activity.

Even better, as the only catamaran tour in south Maui, you’ll have the seas (mostly) to yourselves. Tours are offered Monday through Friday and last approximately 2 hours.

BOOK SUNSET SAILING CRUISE

Nearby Areas: Maalaea  •  Kihei • Wailea

Makena Sunset Sailing Cruise Photos

Book online now!

9 reviews for makena sunset sail.

Beryl T – April 26, 2020

This was my third time on this beautiful boat. For anyone choosing sunset cruises in Maui this is the one. I’d always rather pay a little more to have an uncrowded boat. This is a big catamaran that sails, and it only takes a small number of passengers so get a roomy private feel to the trip. I’ll do this one again and again. Thank you so much for everything! Your staff are always so friendly and helpful. My husband jokes that next time he’s going to sit on the nets upfront and not move an inch, letting everyone wait on him as he stares at the water. I might join him! Hahaha!

Toni Ribet – March 15, 2021

very good. pleasantly surprised at how welcoming the experience was. I’ll be back.

Alan N – May 9, 2021

What a beautiful boat you run! The last boat I was on was in Columbia. It was smaller speedy boat, but it was very fun and the snorkeling was good. This was more luxurious and peaceful. My lady preferred this one, as did I. If I ever make it big, I’m buying a sailing catamaran like yours and sailing around the Caribbean or Med. ahhh! That’s the life. Thanks again!

Cynthia Holloway – December 26, 2021

I always feel like a rockstar when on this boat cause there are very few people on it. A big sailing catamaran for just me and my friends… and new friends. I love this boat and will go out on it every time I go to your island.

Lawrence Schweitzer – March 1, 2022

Last time we did a sunset tour (4 years ago thanks to COVID), we booked through Snorkel Bob. the trip was not worth the money. Sunset was pretty spectacular but they put us on a small boat with a million people. This time we decided to spend a little more money for something better. And WOW, was it ever better! This was one hundred times better than the last trip. The sunset wasn’t even quite as impressive as the one from the previous trip, but it didn’t matter. the boat is luxurious, food delicious, staff warm and helpful, and the drinks bomb.

Larry Diaz – July 7, 2023

I’m not great on boats. Thankfully it was a clear and calm evening. But I think it also had to do with being on a catamaran that made it easier on me. I’ve been on the single-hulled boats and it kills me. We saw a beautiful sunset casting an array of orange hues over the horizon and reflected off of the ocean. I felt so blessed to have had and agreed to this opportunity. If you’re looking for a unique way to experience Maui, this is it!

Deb Evans – July 24, 2023

The crew was incredibly friendly and knowledgeable, providing us with detailed descriptions of the various regions and islands along our voyage.. They also made us tasty snacks and drinks throughout the tour. I was pleased with everything, especially the sunset!

Kev Phillips – January 26, 2024

A heads up, when they say to come in the cabin for pupus, it’s not what you think.

Michelle – March 21, 2024

The boat left from the shore in Makena, and within minutes we were surrounded by magnificent views of the ocean and nearby islands. The sailboat was very spacious, with plenty of seating and standing room to take in the views. They don’t overcrowd the boat, which is much appreciated.

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Couples Only Trilogy Sunset Dinner Cruise

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• Sunset Cruises

Romantic Sunset Dinner Cruise

THIS IS ONE OF THE FEW BOATS LEFT AFTER THE FIRE TO DO A DINNER CRUISE. PLEASE RESERVE FAR IN ADVANCE

Join the Captain on a romantic sunset dinner sail aboard Trilogy’s Luxury Sailing Catamaran!  This sunset sail is for couples only!  It will be a romantic evening of fine dining and beautiful sunsets. Departing out of Maalaea Harbor. Price is per person,if you’re a couple please put 2 in  for head count .

Enjoy Romance, Cocktails, and a Hawaiian Sunset over the Pacific Ocean on Maui’s newest Sunset Dinner Cruise.  Our Romantic Sunset Dinner Cruise is a step above most Maui Dinner Cruises! This Dinner Cruise is on a large luxury sailing catamaran with a small passenger count and seating is set for couples only!  Trilogy’s ‘Captains Dinner’ is your best choice for a romantic Hawaiian Dinner Cruise on Maui.

Trilogy Excursions is the oldest family-owned and operated activity and sailing business in Maui. They own a fleet of beautiful sailboats.  In addition to preserving the ancient art of sailing, they also are preserving the lost art of island hospitality.  After sunset, they give you a little star gazing story time which is very interesting.  They even provide a cozy blanket in the winter months when the air is a little chilly.

The dinner is awesome.  Under the direction of executive Chef Bailey, each course has been thoughtfully put together using fresh, local ingredients, creating a masterpiece for your taste buds.

Pair that with a glass of champagne, outstanding service, and postcard-worthy scenery, and you have a dinner you’ll remember for a lifetime.  Wow-what a beautiful boat and an incredible sunset dinner trip!

Trilogy’s Dinner sail is available for  Adults 18 years and older only.

Additional information

What to Bring:

Your appetite and a camera!  Dress is casual dressy but just remember you are on a boat.

1. Appetizers:  Items are subject to change without notice -Freshly-baked breadsticks dusted with Ala’e Sea Salt with Lilikoi Butter -Smoked Salmon “Wedge”, Crispy Pita & Fresh Dill -Maui Onion Cream Cheese Topped Cucumber -Tataki-style Beef Tenderloin on Crostini 2. Salad : Trilogy Caesar Salad 3. Dinner Options:  (Pick One) -Pan Seared Fresh Rosemary & Garlic Crusted Steaks-

-Citrus Zest Scented Gourmet Chicken Breast -Wild Caught Mahi-Mahi Sauteed and topped with a Lemon Butter Caper Sauce -Seasonal Vegetarian Pasta *All served with sauteed vegetables and roasted garlic mashed potatoes. 4. Dessert:  Trio of Lilikoi Cheesecake, Fresh Strawberries, and Dark Chocolate Truffles

Trilogy’s Dinner sail is available for Adults 18 years and older only

An open bar that includes: Moloka’i Mule, Lana‘i Tai, Maui Brew Co.’s seasonal beer, Longboard, Bud Light Platinum, Champagne, Chardonnay, & Rosé.

Maui Sights & Treasures Cancellation Policy: NO refunds or changes within 48 hours of activity unless otherwise stated. A 10% cancellation fee will be applied to all cancellations made outside of 48 hours of the activity.

Please note: We require all bookings to be made at least 48 hours in advance of the event so that we can guarantee your reservation. If you would like to book an event within the next 48 hours, please call us toll free at 1-888-841-9155 and we would be happy to assist you.

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Luxury Maui Sailing Charters

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Our Sailing Tours

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Embark on an exceptional sailing charter with an Ali’i Nui voyage, where our dedicated crew crafts unique experiences infused with the warmth of aloha. Step aboard our 65-foot luxury catamaran cruises with a shaded cabin, spacious deck areas, and two bathrooms. Immerse yourself in a meticulously curated adventure designed to deepen your connection to Hawaiian culture. Select from our award-winning huaka’i (excursions), each tailored to provide guests with the royal treatment – from our attentive crew catering to all requests to our impressive selection of top-shelf beverages and hoʻonanea (indulgent) culinary offerings. Whether you choose a memorable sunset sail or an exhilarating snorkel tour, Ali’i Nui Maui guarantees an elevated and unmatched sailing experience.

Deluxe Snorkel

Sunset dinner cruise.

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Sunset Sail

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Explore one of Maui’s premier Pali Coast snorkel locations followed by a leisurely cruise taking in the full beauty of Maui. This trip is perfect for those thrill-seeking individuals that are looking for a fun-filled experience.

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Spend the most romantic day of the year aboard Maui’s most luxurious catamaran, as you bask in the Hawaiian sunset’s warm glow and dine like royalty. Learn More

4th of July

Come aboard Maui’s finest sailing catamaran, Alii Nui, for an exclusive 4th of July experience like no other! Alii Nui offers a unique sailing experience with exceptional food and panoramic ocean views! This special event combines our Royal Sunset Sail with an upgraded menu, a full premium bar and a spectacular fireworks show over Maui’s coast. Learn More

Halloween Sunset Costume Cruise

Celebrate Halloween in style with a Sunset Costume Cruise and free admission to Da Playground's Monster Masquerade Halloween Concert featuring live local band Espresso. Learn More

Why Choose Us

Elevated sailing experiences, gourmet dining.

Indulge in an immersive gourmet dining celebrating ‘ono (delicious) Hawaiian flavors. Our talented chefs create innovative dishes using local ingredients for an authentic and culturally accurate dining experience.

Eco-Friendly Practices

Showcasing a commitment to Mālama ka ‘aina (taking care of the land), our catamaran employs eco-friendly and sustainable practices to minimize our ecological footprint.

UNRIVALED COMFORT AND SERVICE

From plush seating and premium amenities to our attentive crew, we prioritize your comfort and satisfaction throughout your journey.

COMMITMENT TO AINA

We prioritize sustainability by sourcing local ingredients and partnering with local brands. Choosing our offerings supports the preservation of our island's natural resources and local economy.

Exclusive Luxury Experiences

Romance glows aboard the Alii Nui

The royal treatment for any occasion

Rated Excellent By Our Visitors

Island Activities

Experience maui, helicopter & air tours, stay connected, subscribe to our newsletter, say hello to turtles and farewell to whales.

Dive into the crystal-clear waters of Maui with our “Goodbye Whales, Hello Turtles” special.

Enjoy 20% off

Our afternoon Snorkel trips throughout May 15 .

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Note to women: If you are pregnant, or attempting to become pregnant, do not dive .

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• Sunset Dinner Cruises (8)
• Sunset Cocktail Cruises (9)
• Holiday Cruises (7)

Sunset Cocktail Cruises

• Although Maui is usually nice and warm throughout the year, it can get a bit chilly on sunset cruises once the sun has set so you will want to bring a light jacket or sweater.
• Some boats are considered "barefoot" and your shoes will be collected at the time of boarding, and it is always recommended that if you do wear shoes on a boat, that you choose footwear that is flat or with low heels. You never know when the ocean will get a little bumpy!
• While there is no dress code, many guests use this opportunity to wear aloha attire on Maui sails and cruises, and casual resort attire is a great option as well.
• There are a wide variety of restaurants around many of the cruise departure locations, and you can plan on having dinner before or after your Maui cocktail cruise.
• Sunset cruises on sailing catamarans will usually have a lounging net where you can sit and relax during the cruise. This area is considered a "splash zone" so please be aware that you might get wet when seated on the net.
• Hold on tight! When you are cruising, keep on hand on the boat at all times to make sure you don’t slip and fall.
• Since many of the sunset cruises on Maui offer open bars, you will want to have a designated driver in your group, or utilize a taxi/ride share to get to and from your tour.
• It is customary to give the captain and crew a gratuity if you feel they did an excellent job, and cash tips are always appreciated.

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Latest reviews of Sunset Cocktail Cruises

Great job and lovely team saw whales at the end of April too. They are still here…

So good we booked another!

Fun, relaxing time. The crew were all so good and quick with a drink and a joke. We had such a great time we booked another four next week. Saw whales and a perfect sunset.

A perfect evening!

Nick and his crew made the experience so much more than we expected. The cocktails we supreme and they ensured our glasses were never empty. The photographer did a fantastic job.

Gorgeous Sail

Crew and boat were amazing! Perfect relaxing evening sail with great appetizers and delicious cocktails. Captain had wonderful stories about the history of the area. Definitely recommend this trip for all!

We took the Sunset Sail on the Trilogy I from Maalaea Harbor. The crew was fantastic. Captain Carrie is a wonderful human! We all felt very welcome & the crew couldn't have been more sweet. The drinks were flowing & th ... more e appetizers were tasty. If you're ever in Maui, make sure you take this sunset cruise. You will not regret it.

Amazing views, fun crew and great drinks!

The crew on the cruise were super fun and made sure to engage with everyone. The cocktails were fantastic and were served quickly. The food was good, a plate of appetizers was served to each guest, so not a choice if the ... more re was something you didn't care for or wanted more of. The sunset was spectacular! I would absolutely do this cruise again.

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Valley Isle Spearfishing

Hours updated 3 months ago

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Kihei, HI 96753

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Mention Yelp when you call to reserve your Dive! Now booking excursions as soon as within one week. Yelpers receive a discount on their first adventure with us. Take An Exciting Adventure of a Lifetime With Some of Maui's Best Spear-fishermen and Experience the Waters of Maui Like Never Before …

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Valley Isle Spearfishing is your best choice for a guide on Maui! The value cant be beat and I had an incredible time with Jordan while learning so much. He took the time to teach me what I needed to be successful in the water as well as staying safe. I asked for a specific mission and he delivered 100%. His knowledge of the ocean and the best spots was impressive and I found myself with more opportunities than I ever expected. I cannot wait for my next trip. Call and book yours now with the best guide around!

Jordan @ Valley Isle took us to a great fishing spot and let us know which kinds of fish tasted the best. He had everything we needed to spear fish and we fished until we needed rest. 10/10

Such a great time, Jordan was a great guide and we were able to see a great variety of fish and a bunch of sea turtle. Spear fishing is definitely something you should do while on the island. 3 fish for the books ! Thank you Jordan !

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Snorkeling and Sailing Charters in Wailea, Maui

Popular maui tours.

• User All ages
• Hour Glass 3.5-4.25 Hours

Sunrise Deluxe Snorkel

The most exclusive tour on Maui, snorkeling Molokini before any other snorkel boats arrive. Hot cinnamon rolls, a three-course breakfast, plus an open bar make this the best morning of your visit to Maui.

• Hour Glass 2-2.75 Hours

Adventure Whale Watch

Sail with our attentive crew and naturalists as we welcome Pacific humpback whales to their winter home. Our beach-loading location gets you on the water and in nature easily.

MOST POPULAR

Signature Deluxe Molokini Snorkeling Tour

FROM $249.46

Snorkel Molokini and enjoy up to 200 ft. of visibility on our classic Maui adventure. An open bar, Maui Brewing beers and full-service deli lunch in three courses complete the perfect day!

About Kai Kanani

We are a family-owned, 30+ year-old company committed to the quality of your experience in our marine sanctuary. South Maui and the Wailea-Makena area are prized for their beautiful beaches, calm and clear emerald-blue waters, and near perfect weather year round. We gratefully acknowledge our kuleana (responsibility) as caretakers of this South Maui paradise. As a company, we treat each other, our guests and our neighbors with Aloha and respect and we believe that is what keeps Maui such an amazing and beautiful place to visit and to live.

The Kai Kanani II is the only commercial catamaran that lives in South Maui, moored off of Maluaka Beach in Makena. Seven days-a-week, she takes passengers on the short cruise out to Molokini Crater, just 3 miles away, to swim and play in the clearest water in all of Hawaii. Five nights-a-week, the Kai Kanani II raises her sails, taking advantage of our famous afternoon trade winds on our Adventure Sunset Sail. These trips and other special offerings are all crewed by the best group of men and women to grace the blue channels of these islands. Their goal is to create the best memories you’ll take home after your time on Maui.

We feature fresh island foods, all curated by Wailea’s own Spoon & Key Market, a chef-inspired deli and restaurant using ingredients that are locally-sourced and house-cured. Our bar features Maui’s Organic Ocean Vodka, Kula Rum, Fy Gin and wines from MauiWine in Ulupalakua. Kai Kanani’s tours are saturated in local experience and cuisine so that you go away feeling connected and refreshed.

The Beach-Loading Pros

South Maui has a unique beauty unlike anywhere else on the island. For a boat company, there’s one very important feature: there are no boat harbors!

Because of this, Kai Kanani’s passengers “beach-load,” walking through the surf and up on to our gorgeous 65-foot catamaran. Our crew are experts at beach-loading, taking pride in our ability to get everyone of our guests on board as dry and safe as possible for your upcoming tour

For us, it’s part of the adventure! So come prepared to get a little wet while getting on-board. Then sit back and relax while our crew takes care of your every need during your adventure in Maui. Kai Kanani Sailing Charters staff is here to help you and make your adventure on the Kai Kanani II memorable, safe & fun. Let us know if you have any questions or concerns about any part of your excursion with us or any other part of your Maui vacation . We look forward to seeing you out on the water and we’ll see you on-board!

What shoes should you wear? We suggest sandals or flip-flops, shoes that are easily removed as you walk across the beach barefoot. And please bring a towel! Once on board, you’re welcome to wear your sandals or whatever type of shoe you’re comfortable in.

Over 1,000 5-Star Reviews on TripAdvisor

Such a great time. We had so much fun with Capt Anthony, Mikey, Eric, Adam, and Dwight. The food was fabulous. Sounds crazy, but true. Great drinks. Beautiful music. A little slice of paradise in the evening. Highly recommend!

The sunset adventure cruise was fantastic. The captain and crew were welcoming, fun, and informative. Four light courses were served during the cruise and champagne was passed around during sunset. Would recommend for couples or friends looking for a chill evening.

We had an amazing day! We were picked up at our hotel and taken to the beach to meet our catamaran. Then -Crater, fish eel, turtles - breakfast, snack, lunch, ending with cocktails. Service was outstanding! Highly recommend!!!!

A true highlight of our trip to Maui! This tour was wonderful! The crew was beyond friendly & helpful, the snorkeling at the crater & additional stop to swim with sea turtles was truly amazing! The food was fabulous too! Would not hesitate to do this tour again!

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Sailing Tours in Maui: A Journey through Oceanic Wonders

Welcome to the serene and spectacular landscapes of Maui, a place where the ocean unveils its secrets and the winds whisper tales of the seas. Sailing Tours in Maui are a gateway to a world filled with azure waters, vibrant marine life, and heavenly sunsets. Whether you’re an avid sailor or a marine enthusiast yearning for new experiences, the sailing tours here offer an array of unforgettable adventures.

The Enchanting Beauty of Maui

Maui, the second-largest of the Hawaiian Islands, is a treasure trove of natural beauty and marine wonders. It’s a place where the mountains meet the sea, creating breathtaking landscapes that leave visitors in awe. The island’s diverse ecosystems and rich cultural heritage make it a sought-after destination for travelers seeking both relaxation and adventure.

The warm tropical climate, coupled with the gentle breezes of the Pacific, provides ideal conditions for sailing. The crystal-clear waters and abundant marine life make every sailing tour a unique experience, allowing visitors to immerse themselves in the enchanting beauty of the ocean.

Embark on Diverse Sailing Adventures

Maui offers a plethora of sailing tours tailored to cater to the diverse preferences of its visitors. Whether it’s the thrill of snorkeling or the tranquility of a sunset cruise, there’s something for everyone.

Maui Snorkeling Tours

Delve into the underwater paradise of Maui with Maui snorkeling tours . Witness the vibrant coral reefs teeming with a myriad of fish species, sea turtles, and other exotic marine creatures. The clear waters offer excellent visibility, ensuring a mesmerizing snorkeling experience.

Guided by experienced instructors, even beginners can safely explore the underwater world and get up close to its inhabitants. The snorkeling spots are carefully chosen to offer the best conditions and marine life sightings, making the tours suitable for both novice and experienced snorkelers.

Sunrise Snorkel Maui

Experience the serene beauty of the ocean at dawn with sunrise snorkel in Maui . As the first rays of the sun light up the sky, the ocean reveals its true colors, offering a unique and tranquil snorkeling experience.

The early morning calm provides ideal conditions for snorkeling, allowing you to explore the reefs in peace, without the crowds. The rising sun enhances the underwater scenery, illuminating the coral formations and marine life in a soft, golden glow. It’s a magical experience that leaves a lasting impression on all who witness it.

Wailea Sunset Cruise

Conclude your day in Maui with a magical Wailea sunset cruise . Sail along the picturesque coastline as the setting sun paints the sky in vibrant shades of orange, pink, and purple. The gentle sea breeze and the soothing sound of the waves create a romantic and relaxing atmosphere, making it a perfect way to end your day.

As you cruise along the calm waters, keep an eye out for dolphins, whales, and other marine life that frequent the area. The panoramic views of the sun setting over the Pacific Ocean are truly mesmerizing, offering ample photo opportunities to capture the moment.

Expert Guidance and Safety

Whether it’s your first time on a sailing tour or you’re a seasoned sailor, the experienced and friendly crews ensure your safety and enjoyment throughout the journey. They share interesting facts and stories about the local marine life and ecosystems, enriching your sailing experience.

All necessary equipment and instructions are provided, ensuring a smooth and enjoyable experience for everyone on board. The crew’s local knowledge and expertise allow them to choose the best spots and routes, maximizing your chances of witnessing the diverse marine life and scenic beauty of Maui.

Conclusion: A Nautical Journey Like No Other

Sailing tours in Maui offer an unparalleled opportunity to explore the pristine waters and witness the vibrant marine life of the island. The diverse range of tours available caters to all preferences and skill levels, ensuring a memorable experience for everyone.

Whether you’re exploring the colorful coral reefs, witnessing the serene beauty of a sunrise, or enjoying the romantic ambiance of a sunset cruise, sailing tours in Maui promise a nautical adventure like no other. So come, set sail, and let the winds guide you through the enchanting waters of Maui, creating memories that will last a lifetime.

Explore the Magic of Molokini Crater Snorkeling

Discover the enchanting world beneath the waves with molokini crater snorkeling , a must-do adventure for anyone visiting Maui. This crescent-shaped, partially submerged volcanic crater offers crystal-clear waters, vibrant coral reefs, and a plethora of marine life, making it an ideal destination for snorkelers of all levels.

Why Molokini Crater is Unique

Molokini Crater, a protected marine conservation area, is renowned for its exceptional water clarity, with visibility often exceeding 100 feet. The crater’s unique geography creates a natural sanctuary for hundreds of fish species, many of which are endemic to Hawaii. From the colorful parrotfish to the elusive octopus, Molokini offers an underwater spectacle that is second to none.

What to Expect When Snorkeling at Molokini

When you embark on a molokini snorkeling adventure, you’re in for an experience of a lifetime. The crater’s calm and clear waters make it perfect for beginners, while the diverse marine life and underwater terrain offer plenty to explore for the more experienced snorkeler.

Preparing for Your Snorkeling Trip

Before you dive into the waters of Molokini, it’s important to prepare. Make sure to choose a reputable snorkeling tour that prioritizes safety and environmental conservation. Additionally, familiarize yourself with Maui snorkeling techniques and equipment to ensure a comfortable and enjoyable experience.

Environmental Conservation Efforts

Preserving the natural beauty of Molokini Crater is a top priority. As visitors, it’s our responsibility to respect and protect this delicate ecosystem. By choosing eco-friendly tours and adhering to conservation guidelines, we can help ensure that Molokini remains a pristine snorkeling destination for generations to come.

Additional Snorkeling Spots Around Maui

While Molokini Crater is a jewel in Maui’s crown, the island offers numerous other snorkeling spots worth exploring. From the vibrant coral gardens of snorkeling in Maui to the serene waters of Kapalua Bay, each location offers its own unique charm and marine life.

As you plan your snorkeling in Maui adventure, remember that the island’s beauty extends beyond its beaches. The rich cultural heritage, lush landscapes, and warm Aloha spirit make every visit to Maui an unforgettable journey.

Embarking on a Molokini Crater snorkeling trip not only offers an opportunity to explore one of the world’s most exceptional underwater environments but also invites you to become part of a community dedicated to preserving the beauty and diversity of Maui’s marine life. Dive in and discover the magic that lies beneath the surface.

Catch The Sun: 10 Perfect Spots to Watch The Maui Sunset

I ndulge in the awe-inspiring beauty of Maui as the radiant sun gracefully descends below the horizon, illuminating the sky with shades of orange, pink, and purple. Boldore planning a Hawaii vacation, discover the most idyllic spots that provide the perfect vantage points to witness the sun's magnificent farewell on this captivating Hawaiian island.

From the renowned Haleakala Summit, where the boundaries between earth and sky blur, to the serene shores of Kaanapali Beach, where the setting sun playfully dances upon the tranquil waves, each of the best Maui sunset spots presents a distinct perspective to behold the captivating spectacle as the day ends.

Related: 10 Best Maui Waterfalls That Unveil Nature's Majestic Beauty

Haleakalā Summit

At the pinnacle of Haleakalā, a mesmerizing sight awaits as ethereal clouds burst into vibrant shades of orange and red, creating an awe-inspiring spectacle that makes it an ideal spot to witness the enchanting sunset. The summit of Haleakalā offers unparalleled vistas that take one's breath away.

With wispy clouds ablaze in fiery hues, this remarkable location provides a perfect vantage point to capture the captivating beauty of the setting sun. Prepare to be captivated as one embraces the extraordinary experience atop Haleakalā, where nature's artistry unfolds before one’s eyes.

Haleakalā is also considered one of the best spots to watch the sunrise in Maui , making it the perfect place to spend the day from early morning to the evening.

• Location: in the Haleakalā National Park , 30,000 Haleakalā Hwy, Kula, HI 96790
• Setting: breathtaking vistas from a high vantage point
• Hiking difficulty: over 30 miles (48 km) of hiking trails, ranging in difficulty from beginner to advanced

Some hikes at Haleakalā can last a full day, so pack accordingly.

Kāʻanapali Beach

Situated along the western coastline of Maui, Kāʻanapali Beach emerges as a true gem, boasting three miles of pristine white sands and mesmerizing aquamarine waters. It is considered one of many unique Maui beaches to explore and can even rival many of the best beaches in the US in terms of beauty.

As the sun begins its descent, the sky becomes a canvas of vibrant colors, harmoniously blending with the captivating backdrop of Puʻu Kekaʻa, famously referred to as Black Rock. This iconic location offers an exhilarating spectacle, where courageous divers gracefully plunge into the ocean from the towering cliffs.

With the stunning combination of nature's palette and daring feats, Kāʻanapali Beach becomes an irresistible destination to witness the enthralling beauty of a sunset on the enchanting island of Maui.

• Location: on the west shore of Maui, Hawaii, in the Kāʻanapali resort area
• Setting: three miles of pristine white sands, backdrop of Puʻu Kekaʻa (Black Rock)

Kapalua Bay

In proximity to Kāʻanapali Beach lies the captivating Kapalua Bay , where breathtaking sunset vistas unfold, accompanied by the picturesque silhouette of Molokaʻi, known as the Friendly Isle, on the distant horizon. As one basks in the serene beauty, keep a keen eye out during the winter months, for one may be fortunate enough to catch a glimpse of playful whales gracefully frolicking in the nearby waters.

Offering a seamless blend of natural splendor and marine wonders, Kapalua Bay stands as one of the most beautiful places in Maui to watch the sunset, creating cherished memories that will last a lifetime.

• Location: in Kapalua, Maui, Hawaii, along the northwest coast of the island
• Setting: the picturesque silhouette of Molokaʻi, known as the Friendly Isle

Mākena (Big Beach)

Nestled along the southern coast of Maui, Mākena, affectionately known as Big Beach, presents an esteemed destination to behold the enchanting radiance of the setting sun. This beloved shore, which is considered one of the best beaches in Maui for sunsets, finds itself embraced by lava outcroppings, creating a striking backdrop that adds to its allure.

As twilight descends, visitors flock to this picturesque spot, eagerly awaiting the mesmerizing display of colors that paint the sky. With its idyllic setting, captivating vistas, and unique lava outcroppings decorating the landscape, Mākena stands as a popular choice for those seeking to immerse themselves in the beauty of a sunset in Maui.

• Location: in Mākena State Park in the South Beach region of Maui
• Setting: beach surrounded by lava outcroppings

Keawakapu Beach

Situated along the sun-kissed southern coastline of Maui, Keawakapu Beach is another one of the top sunset spots in Maui. Here, visitors can witness awe-inspiring sunsets, conveniently sparing one the need for a lengthy drive to Mākena.

This cherished beach offers an idyllic vantage point where visitors can immerse themselves in the breathtaking beauty of the descending sun. With its inviting shores and captivating ambiance, Keawakapu Beach becomes a go-to spot for those seeking to be captivated by the magical allure of Maui's sunsets.

• Location: in South Maui, between Kihei and Wailea, at the end of South Kihei Road in Hawaii
• Setting: idyllic beach

Napili Bay Beach

In proximity to Kapalua, Napili Bay Beach is one of the most beautiful places to watch the sunset in Maui, as locals and tourists alike congregate to witness the captivating spectacle of sundown. Whether one chooses to set up comfortable lawn chairs on the lush grass or prefers to soak in the scene from the sandy shoreline, this popular spot offers a picturesque setting to savor the mesmerizing colors as the sun bids its farewell.

With a sense of community and an inviting ambiance, Napili Bay Beach provides an inviting haven where one can relish the beauty of the sunset, creating cherished memories in the embrace of this scenic Maui gem.

• Location: in Northwest Maui
• Setting: sandy shore or lush green grass

Polipoli Springs State Recreation Area

For those seeking an extraordinary sunset encounter, a visit to Polipoli Springs State Recreation Area is highly recommended. Positioned at elevated altitudes, this park presents a remarkable vantage point that showcases panoramic vistas of Maui's stunning landscapes, offering a fresh and distinctive perspective for witnessing the setting sun.

With its unique setting and awe-inspiring views, Polipoli Springs State Recreation Area promises an unforgettable sunset experience that will leave visitors captivated by the beauty of Maui from a whole new angle.

• Location: about ten miles from Kula, up the slope of Haleakalā
• Setting: view from an elevated level that showcases panoramic vistas of Maui

Related: 9 Maui All-Inclusive Resorts To Immerse Yourself In Endless Delights And Tropical Luxury

Lahaina Pali Trail

While it may present a moderate challenge, the Lahaina Pali Trail stands as a prime location to witness the majestic sunset on Maui. This is one of the most beautiful sunset hiking trails in Maui and offers hikers a gratifying experience, as they are bestowed with panoramic vistas that overlook the central valley, unveiling a breathtaking spectacle of the sun bidding farewell over the vast expanse of the North Pacific.

Though the trail may test people's endurance, it is considered one of the best hikes in Maui , and the rewarding views make every step worthwhile. Prepare to be captivated by the awe-inspiring beauty that unfolds before one’s eyes as one conquers the Lahaina Pali Trail and embraces the unforgettable splendor of a Maui sunset.

• Location: between the south side of West Maui and the central valley, passing over the West Maui Mountains
• Setting: panoramic views of the central valley
• Hiking Difficulty: the trail is approximately 5 miles long and is considered quite advanced

Wailea Beach

Situated within the Wailea Resort area, home to resorts, hotels, and beautiful Maui vacation rentals , Wailea Beach is among the best sunset-watching spots in Maui. With its glistening golden sand and translucent waters, this beach offers a tranquil ambiance that sets the stage for a serene sunset experience.

Immerse oneself in the peaceful atmosphere as the sun gracefully descends, casting its warm hues across the horizon. Whether one chooses to stroll along the shoreline or simply bask in the serenity of the surroundings, Wailea Beach provides the perfect haven to unwind and savor the breathtaking allure of the setting sun.

• Location: within the Wailea Resort area

Related: 10 Best Snorkeling Spots In Maui Where You Can Explore Its Maritime Beauty

Hanakao'o Beach Park

Nestled close to Kaanapali Beach and Lahaina Town, Hanakao'o Beach Park presents a serene and tranquil setting to create one of the best places to see the most beautiful sunsets in Maui. This hidden gem offers a peaceful escape, providing a quieter alternative to enjoy the captivating colors of the descending sun.

With its well-appointed picnic areas complete with BBQ grills, the park invites visitors to unwind and indulge in a leisurely experience, allowing one to fully immerse oneself in the mesmerizing beauty of the sunset. Whether visitors are seeking solace or quality time with loved ones, Hanakao'o Beach Park promises a serene haven where one can relax and embrace the scenic majesty as the sun paints the sky in vibrant hues.

• Location: at the southern tip of Ka'anapali Beach on the west shore of Maui
• Setting: peaceful spot with picnic areas complete with BBQ grills