Key Largo Adventures

Islamorada boat tours, snorkeling, & more, new luxury pontoon boat upgrade bbq grill option. call/text or click 305-975-4885.

  • Most popular!

Half-Day Multi-Activity Charter

Come to the Florida Keys and enjoy our Multi-Activity Charters to the Sandbar, and add either snorkel at the reef or bayside sights. Explore the Islamorada Sandbar on stand-up paddle boards. Relax on floats. Dance to bluetooth stereo. Bring a lunch/snacks/drinks aboard, or upgrade to boat with BBQ Grill!

  • Hour Glass 3 or 4 hours

Most Popular Islamorada excursions

  • Hour Glass 6 hours

Full-Day Private Multi-Activity Boat

Come to the Florida Keys and enjoy our Multi-Activity Charters to the Sandbar, and add either snorkel at the reef or bayside sights. Explore the Islamorada Sandbar on stand-up paddle boards. Relax on floats. Dance to bluetooth stereo. Bring a lunch/snacks/drinks aboard or upgrade to boat with BBQ Grill!

  • Hour Glass Flexible

Large Groups & Customized Charters

Customize your Key Largo Adventure boat tour to create the perfect day in Islamorada! Choose from many amenities, like snorkeling, fishing, exploring the flats and more.

  • Best Value!
  • Hour Glass 3 to 6 hours

Islamorada Sandbar Boat

Key largo adventures activities.

Key Largo Adventures offers multi-activity charters. Full-day, half-day, and customized tours allow you to relax and enjoy the natural environment, go sightseeing, or combine other activities at the Islamorada Sandbar or mangrove islands for one affordable all-inclusive price. Check out the best Islamorada snorkeling tours and more. Book your Islamorada boat charters near Key Largo now!

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Sandbar, Snorkeling, Paddleboarding, Boat Tours

About key largo adventures.

Key Largo Adventures is a five-star TripAdvisor-rated tour company. Our guests agree that we are the best all-inclusive, private Islamorada charter boat tour in the Islamorada area, offering a multi-activity charter. Our full-day , half-day , and other customized Islamorada boat tours depart from Island Grill, 85501 Overseas Hwy, Islamorada, Florida 33036.

Captain Charlie Filpes of Key Largo Adventures offers a sensational, private, all-inclusive boat charter and customized tours in the upper Florida Keys. Details of each Key Largo tour can be found by choosing an option above.

The captain and his first mate provide five-star service aboard the TIKI TIKI, the 25-foot open fisherman, which will thrill even the biggest of water sports enthusiasts. Instead of renting a boat and being your own captain, you become free from responsibilities and have your own private crew taking great care of you and your guests. We look forward to taking you, your family, and friends on a private all-inclusive adventure you won’t soon forget on this fun-filled day on the water. Enjoy a fantastic Islamorada charter boat tour with us. Experience paddle boarding in Islamorada, boat trips, snorkeling, and more.

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5-Star Islamorada & Key Largo Boat Tours

had so much fun with Key Largo Adventures and iRocker Paddle Boards. It was definitely an adventure to remember. Captain Charlie was always there to capture the fun with photos (which we received really fast!) I will surely be recommending him to my friends and can't wait to go out with Key Largo Adventures again!

Another amazing day with Captain Charlie and Claire. We have 4 kids aged 7-15 and everyone had a blast!! Captain Charlie took pictures during the trip and sends them to us - including underwater- can’t wait to see! He was easy to plan with via text and really knowledgeable about fish and the Keys.

Loved our time with Key Largo Adventures! Captain Charlie provided everything we needed for a fantastic day on the ocean. My husband and I, along with our three kids, had the most memorable day. We loved it and will definitely book another charter the next time we are in the Keys.

My husband and I booked a charter with Captain Charlie for the day and we had an absolute blast! He is such a fun, down to earth guy who works VERY HARD to make sure you have the time of your life! Boat was spacious, nice and clean, the meal that he prepared for us was delicious and we enjoyed him playing every single song request.

florida keys sailing tours

Private & Shared Sailing Charters

Sunset sail key west.

Have the sea to yourself with Sunset Sail Key West—chartered sailing trips led by us, tailored to you.

florida keys sailing tours

Get inspired with our most popular trips!

Private sunset sail.

florida keys sailing tours

Chillout Lilypad Sail

florida keys sailing tours

Key West Daysail

florida keys sailing tours

Sunset Sail on When & If

florida keys sailing tours

Privates Charters

Discover your perfect private charter.

Set out on a snorkeling, stargazing, or sunset sail, or build your own custom trip. Romance, relax or unwind from the privacy of your own chartered sailboat.

florida keys sailing tours

Shared Trips

Come together on a shared charter.

Rise above the crush of the crowds and set sail on a unique shared sunset charter, with a few friends you haven’t met yet. A personable local crew and captain will treat you to a stunning sunset view from the deck of an unforgettable vessel– General Patton’s elegant, private schooner When and If.

florida keys sailing tours

Three Classic Boats

View our fleet.

We sail a fleet of three vintage sailboats, each with their own unique charm and appeal. A custom sloop, a classic ketch, and a historic schooner are waiting to make memories with you on the crystal clear waters of Key West. Each boat is suited to different types of outings, so take a moment to get acquainted with our vessels.

Real. Fun. Sailing.

florida keys sailing tours

When And If is back at beautiful Stock Island Marina!

florida keys sailing tours

Check Out Our Ship's Store!

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Wreckers' Race Season Is Back!

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Hello, Sailor! Don’t miss out on the latest Sunset Sail news & offers.

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Friends of SSKW

Legal & safety.

florida keys sailing tours

Shared & Private Key West Boat Tours

Memories to last a lifetime, explore key west like never before.

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Amazing Destinations

World-class Key West destinations just a short boat ride away

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Experienced Captains

Trust our experienced captains so you can focus on total relaxation

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Super Fast Booking

Real time availability and instant confirmation for your upcoming trip

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Affordable rates

We’ll make the most of your Key West vacation without breaking the bank.

Private boat tours in the heart of paradise

Key West Boat Trips is your ultimate gateway to an unforgettable maritime adventure in Key West. 

Step away from the bustling crowds and embark on a journey that caters exclusively to your preferences and pace. Whether you’re looking to bask in the sunshine aboard one of our premium tour boats or take an exhilarating ride on a brand new e-foil, we offer a myriad of experiences tailored to your desires. 

Choose from our wonderous activities like snorkeling among the sealife, swimming in crystal-clear waters, hopping from one idyllic sandbar to another, or unwinding on a scenic sunset dinner cruise.

Our destinations are nothing short of spectacular, featuring the serene Mud Keys, the stunning Boca Grande, and other remarkable locales where the majestic Florida dolphins often make an appearance. Each journey is steered by our seasoned captains, experts in navigating the waters of Key West and in providing you with a safe, enjoyable, and enlightening experience.

We pride ourselves on our flexibility and convenience, offering real-time booking availability to seamlessly plan your trip. Our rates are designed to provide you with an affordable yet premium experience, ensuring that luxury and adventure don’t have to break the bank. Step aboard our upgraded boats, where comfort meets elegance with stitched leather interiors and state-of-the-art sound systems, enhancing your aquatic expedition.

No prior boating experience? No problem. All our charters are captained by professionals with an intimate knowledge of the area, allowing you to sit back, relax, and enjoy the journey. Moreover, every excursion includes the essentials for a day at sea — fuel costs are covered, and a cooler stocked with water bottles and ice is provided to keep you hydrated under the sun.

Dive into the heart of Key West with Key West Boat Trips. Discover the beauty, thrill, and tranquility of the ocean with us, where every trip is more than a journey — it’s an experience to remember.

Our Guided key west boat tour packages

Let's go to your happy place, shared hopping sandbars in key west, 30min boat ride each way 2 hours on sandbars, 30min boat ride each way 3 hours on sandbars.

Discover Key West’s hidden gems on our intimate boat journeys, tailored for the solo traveler, romantic duos, or close-knit groups. Dive into crystal-clear waters, relax on serene sandbars, and revel in nature’s untouched beauty, all at an unbeatable price.

With a cap of six guests, every experience promises personal touches and unforgettable moments. Embark with us for an adventure where luxury meets the wild, crafting memories that last a lifetime.

Starting From

florida keys sailing tours

Hopping Sandbars in Key West

On this Key West boat tour, you get to see not one, but several different sandbars. We’ll take only 25 minutes to go there on our epic excursion–but we’ll stop for as long as you want at those that interest you the most. All-in-all, it’s an experience unlike anything else offered here!

See the mangrove trails of Mud Keys and go mingle with locals at Snipe Point sandbar after. You will not want this day to be over.

for up to 6 people

Sandbar Trips for Large Groups

1 hour boat ride each way 1 hour on sandbars, 1 hour boat ride each way 2 hours on sandbars.

If your group is larger than 6 and you have a hard time finding a boat ride to the sandbars because of the 6 passengers limit, we are here to help. You can book our 2 identical Hurricane 27 foot deck boats and our captains will drive them side by side so you can take cool photos and they will raft up the boats on the sandbars so you can enjoy and share this amazing time together.

for up to 12 people

Key west Sunset Cruise

Sunset Cruise in Key West! We are headed to the sandbar and beyond, our skipper will take us out for a private boat tour into the backcountry waters. Watch as we anchor over the sandbar, reaching deep enough for you to jump from just above waist high water and get some awesome pics with the sun setting behind you – it’s really something special.

Key West Dinner Cruise

This Key West Dinner Cruise is the perfect way to enjoy beautiful scenery and a fresh seafood dinner with wonderful friends or family. The whole cruise experience includes an experienced captain taking you to the best location in Key West, with him cooking while you play in shallow turquoise water. You will thoroughly enjoy this unique adventure that people never forget.

Key West Lunch Cruise

This Key West Lunch Cruise starts off by getting on a boat ride that will drift through the beautiful backcountry waters. The boat will dock at its very own sandbar location where you are free to walk around or have an enjoyable swim in clear, shallow water. After snorkeling or simply staying on the boat, we will serve you freshly made lunch!

Mud key Mangrove Safari

Mud Keys Mangrove Safari will have you feeling like a world explorer in our own backyard. After getting onto the boat, we’ll take you for a 30-minute cruise of backcountry waters to Mud Key Sanctuary! Upon arriving there, enjoy nature surrounding you and take pictures while soaking up the sun. You can walk around on the sandbar and swim if you’d like or just soak in all the gorgeous sights the area has to offer.

Boca Grande Island Time & Snorkeling

If you are looking for some beach time on a remote island far far away – this boat trip is for you. Stop on the way for sponge garden snorkeling in just 5 feet of water. At the Boca Grande destination, you’ll take a break from your phone as you will not have any service there. Walk down the beach and enjoy looking at the beautiful turquoise colors of the water surrounding you. If you will feel like exploring further – we will take you near the neighboring islands Woman Key and Ballast Key for some more breathtaking sights. 

Key West E-foil Rides

30 minute boat ride each way 2 hours e-foil session.

Now you can experience surfing’s newest frontier, the electric hydrofoil surfboard on one of our Key West boat tours. Take a 30 minute boat ride to the protected area with calm and deep water. Enjoy a 2 hour session on Lift foil model 3 electric powered hydrofoil surfboard while being coached by one of our experienced captains.

for up to 2 riders 6ppl total on the boat

Key West Private Boat Charters

30-45 minute boat ride each way, 1.5-2 hours anchored on the sandbar​.

Let us bring your family to that magical Key West beach that seems to only exist in calendars and magazines. Sit back, relax, and let the professional captains at Key West Boat Trips take you on backcountry excursion that you’ll never forget. With dozens of world-class destinations, just a short boat ride away, you’ll see why it’s one of the best things to do in Key West.

Key West Dolphin Swimming

Key west glass bottom boat, availability : year round, our boat tour customers rave about us, key west boat trip destinations.

This destination is only a short boat ride away. After just 30 minutes boat riding, we arrive at a mangrove maze made out of series of islands approximately 11 miles northeast of Key West. We will park our boat somewhere knee deep shallow, over a nice sandy bottom – so you can walk around and take pictures, swim or snorkel in turquoise water and sandbars.

Boca Grande

Do you want to see some of Florida’s most beautiful beaches? If so, then the Key West National Wildlife Refuge Island is one stop that should not be missed. It has a gorgeous natural beach and is 15 miles west of Key West. On your way there, you may spot dolphins playing in the water! We can also stop at the sponge garden off one of the islands for some snorkeling. The water here is only 5 feet deep, perfect for families who are looking for an adventure without getting too deep!

Snipe Point*

The sandbar at Snipe Point is a popular destination for locals who spend their weekends boating. This island, often called “Snipes” – is extremely hard to find so boat rentals are unlikely to invade your space. You will be surrounded by locals and their families looking to get away from the hustle and bustle of city life on this gorgeous beach area.

*This destination is recommended on a 4hr trip

Boat Rental Vs Key West Boat Trips

Private boat tours are a great way to see the Florida Keys! The shallow waters can be dangerous for first timers, so it’s best if you let us do the driving! 🙂

Basic Boat Rental

  • Half day $450 plus fuel average cost of deck boat rental
  • Boating experience necessary
  • Very plain and basic boat with low HP motor
  • High risk of running aground in very shallow waters therefore possibility of extra cost to cover damages
  • Credit card hold for $1000+ to cover potential damages
  • Not likely to get to pretty locations as it takes knowledge of local waterways
  • You'll need to fill up the cooler with beverages

Key West Boat Trips

  • Half day $650 with fuel included
  • No previous boating experience needed
  • High end premium boat with 300HP motor
  • With the experienced captain driving no risk of running aground
  • No additional security deposits or credit card holds
  • Guaranteed to go to the prettiest destinations around
  • Cooler full of bottled waters and sodas topped with ice included

FREQUENTLY ASKED QUESTIONS

Most frequent questions and answers.

It has a flushable marine toilet for liquids only. The boat also has fresh water rinse so you can rinse yourself from salt water.

To some extent – yes. Sometimes we will have to because the weather isn’t always ideal and we want to stay in shallow, calm waters to keep the trip enjoyable.

All our trips are private to your group with the exception of a Shared Sandbar Hopping Trip.

Absolutely. Our boat has a premium amplified 9 speaker audio system and you can play music from your phone via Bluetooth.

We have an iced cooler with bottled waters. You’re welcome to bring your own drinks, beers and snacks.

Unfortunately not. We are limited to 6 passengers per boat per our license and each child counts as one just like adults.

Absolutely. We can take your party out on two identical boats. Details in Sandbar Hopping For Large Groups page.

There is always a chance for that and we often do, however we can’t promise that you’ll see them because they swim around freely and do not hang out in the same place.

We do not. We are not a fishing charter and we think that our boat is just too pretty to have smelly fish guts all over it.

48hrs before the scheduled boat trip to get a full refund if you happen to change your plans. All our trips are weather permitting so we reserve the right to cancel your trip if we don’t think that conditions are safe – in this case you would get full refund also.

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Book your next boat trip

Trust the premier boat tour operator in key west to take you for the trip of a lifetime.

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At Key West Boat Trips we take your dream Florida Keys vacation and make it a reality. Let us bring your family to that magical Key West beach that seems to only exist in calendars and magazines.

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Key Largo Princess

Glass bottom boat cruises in key largo, fl.

Tours Available Daily!

Most Popular Glass Bottom Boat Cruises In The Florida Keys

  • Best Seller!

Glass-Bottom Boat Key Largo

Hop aboard the M. V. Key Largo Princess for our daily tour to view the exciting and beautiful underwater world of the John Pennekamp Coral Reef State Park and the Key Largo National Marine Sanctuary. Relax on the sun deck or enjoy our climate controlled cabin as you observe the coral reef through our large viewing windows.

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  • Hour Glass 2 hours
  • Clock 10 a.m., 1 p.m., 4 p.m.

About Our Key Largo Boat Tours

Hop aboard the M. V. Key Largo Princess 2 for our daily two-hour tours as we cruise through the waters of the John Pennekamp Coral Reef State Park to view the exciting, beautiful, underwater world of the Key Largo National Marine Sanctuary.

The Key Largo Princess is a 75-foot luxury, coast guard certified, glass bottom boat, which can hold up to 140 passengers. Relax in the comfortable air-conditioned cabin as you peer into the depths of the Molasses reef or enjoy a panoramic view of the many colors of the sea from our spacious sun deck. Or, soak up the sun on our sun deck as you sip a tropical cocktail or beverage from our full-service snack bar. You’ll love the scenery the John Pennekamp Coral Reef State Park (the only undersea park in the United States) has to offer.

florida keys sailing tours

See Why Visitors Love Cruising With Us!

florida keys sailing tours

My son & I have been on this boat a few times and is something we do every time we visit. It will never get old!

Staff was awesome from the start! They were professional and personable. Great experience all the way through!

We took our 5 year old grandson for his first view of the keys to see the reef! This was a great location to our hotel!

You have a nice friendly crew and great viewing. The reef is among the largest in the world and full of wonders and fish.

Keys Boat Tours

CALL TO BOOK YOUR TOUR TODAY: 1 (305) 699-7166

Say Keys

1 Hour Bridge Loop 1 HOUR

A 1 hour loop around Bahia Honda and the Seven Mile Bridge with Captain Brian. Learn history of the bridges and the Flagler railway.

florida keys sailing tours

Eco Island Loop 2 Hours

A 2 hour loop around Bahia Honda and out to No Name Key and the backcountry with Captain Brian. See the Gulf and the Atlantic sides. Skinny water and beautiful beaches. This is a great way to get on the water, and just may be the best deal in the Keys!

florida keys sailing tours

Patch Reef / Mangrove Snorkel 2 Hours

Let Capt Brian show you lots of tropical fish. Snorkel gear is provided. Feel free to pack a lunch. Need a wetsuit? Add $10. Having fun? Add an hour +$75. The patch reef is a great back-up snorkel spot when the barrier reef is too choppy.

florida keys sailing tours

Looe Key Snorkel 3 Hours

When the conditions are right; light breeze and good visibility, the reef is the place to be. Looe Key is a local pride and joy – most impressive snorkel spot on the only barrier reef in the continental United States. It is an underwater marine sanctuary four miles out to sea that boasts a wide array of coral and colors.

florida keys sailing tours

Mangrove Tunnel Paddle 2-1/2 HOURS

Our motor/paddle option is 2-1/2 hours / $375 (up to 3 paddlers at a time) mangrove cave crawl; motor to a mangrove island, then find your inner monkey and swing from mangrove limb to limb as we discover the inner reaches of No Name Key.

florida keys sailing tours

Fish the FL Keys 4 Hours

Recreational fishing is just that… When someone asks you what you’re fishing for, the answer is – a) snapper, b) jacks c) grouper d) to relax or e) all of the above. The goal is to fish and catch. We only hope that a) the fish are biting and b) you can bring them in the boat. If no signs of bite early in, we’ll change locations – head to a grass channel or out the reef. Ultimate goal: good time fishing!

florida keys sailing tours

Day on the Water 4 Hours

Eco • Paddle • Snorkel • Beach • Lunch: it’s up to you. The backcountry of the FL Keys is a very special place to explore. Located on the Gulf side, we’ll cruise the backcountry to the Content Keys, walk the flats, paddleboard, see the birdlife. Our specialty is families and kids. A fun day on the water!

florida keys sailing tours

Sunset Tour 2 Hours

A sunset in the FL Keys is a magical experience to behold. There are few places on the east coast where one can see the sun set into the water, and this is one of them. Motor or sail, ocean side or Gulf. We depart the marina 2 hours prior to sunset. Bring your own sunset drinks and snacks. We might even take a quick dip–whatever we want. You’re in the Keys!

florida keys sailing tours

Hands-On Boating Lesson 4 Hours

This is the only hands-on boating safety lesson in the Keys. You learn how to: a) dock a boat in different situations, b) drop and retrieve an anchor, c) understand weather, wind, and tides and d) drive a boat. Just one tip from this four hour session could pay for the entire lesson.

florida keys sailing tours

Fishing / Navigation 101 4 Hours

Navigating the FL keys can be difficult with all the skinny water and obstacles in the water. Fishing can be challenging as well…what tackle to use, what bait, where to go and at what time.

Special Charters

florida keys sailing tours

Ceremonies at Sea 2+ Hours

Ceremonies At Sea is just that, a way for anyone and everyone to celebrate a bond, or a life. Captain Brian is ordained and can officiate weddings and memorials alike. Keys Boat Tours provides the charter, and can even provide an island for the occasion.

florida keys sailing tours

Your Tour 2+ Hours

Design your own special tour on the water. It can be a combo tour of something we already offer, or other. Pull through a mangrove tunnel, chill out on a sandbar or island, etc.

Testimonials

Captain Brian is the hands down number 1 boat instructor in the Keys. I recently took my 14 year old daughter to a there hour hands on boating safety course with Captain Brian in Bahia Honda Key. He was absolutely fabulous and my daughter learned, in depth, how to navigate a boat in all manner of conditions including high winds, shifting tides, through narrow channel, docking the boat in various wind conditions, and chart reading. My daughter was captivated and it was very empowering for her to master these skills. Captain Brian has perfected a teaching skill which engages the kids so they really retain the information and have a great time learning. TOM & ALLY
The water was crystal clear, the sea life magnificent, the pelicans close, the Captain gracious, and the sunset backdrop breathtaking!  I cannot recommend this experience any higher!  Bon voyage! LISA FROM IOWA
I recommend the motor boat / paddleboard combo tour thoroughly. It was our first time on paddle boards and Captain Brian made it so easy. SARAH FROM TEXAS
Thanks so much for customizing our boat trip to serve both our needs! JANINA & CHRIS
The protected cove, the rays, the sunset – a perfect outing with Capt Brian. Highly recommended. DOUG & FRIENDS
Thanks to Captain Brian, we had an amazing time on the water. We loved every minute! JAY, LISA & CATHY
Thanks again for helping us today Capt Brian. It was fun, informative, confidence building, and a great first trip out to the reef. KIERAN & MR. C!
Jack and I had wonderful time with you on the water. We see how much you love what you do. You made our trip to the Keys that much more special. MAGGIE & JACK
Thanks to Captain Brian – I learned how throw a cast net in no time! JOHN CHANG

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The Road to Key West

  • BOAT TOURS | LESSONS
  • PRIVATE POLICY

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Florida Keys Boat Charters |  Islamorada Sandbar, Snorkel & Tours  

Cruising-Florida-Keys-Boat-Charters-Sightseeing.HEIC

Islamorada, FL A great location for family friendly events & water activities for visitors. 

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Private Boat Charters in The Florida Keys

Let us take you on an all inclusive fun and/or relaxing trip to visit the world famous Islamorada Sandbar or check out one of the many services we offer! A licensed Captain and a qualified First Mate will be on board to cater to any of your needs with years of experience in boating.

Our PICK-UP location is at IslaMarina - 85920 Overseas Highway, Islamorada, FL 33036 (If you would like to get picked up at a specific location, please feel free to reach out and we will try our best to accommodate you to your needs.)

Please feel free to send us an email/text or call if you have any questions or concerns. 

Email: [email protected]

Phone: (305)776-3694

Family Friendly | Pet Friendly

{Se Habla Español | Mówimy Po Polsku}

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The Hurricane - Deck Boat 24' Vessel

This boat comes complete with a stylish "sea dek" (great for photos) and a JL audio speaker system with a wireless bluetooth connection.  A built-in bimini top will provide shade towards the back half of the boat. Cooler space, ice and waters will be available upon pick-up time. Guests may bring food or beverages on board. This boat charter includes: A stand-up paddleboard, a 9x5 floating water mat, floats, water toys and snorkel gear.

The So|Flow - Our Catamaran/Pontoon 26' Vessel

Built for cruising, not for speed, this boat charter includes : 

2 Stand-up paddleboards for hands on experiences with help for beginners from our staff. A 9x5 floating water mat, floats, water toys & more! A built-in bimini top will provide shade towards the back half of the boat. Cooler space, ice and waters will be available upon pick-up time. Guests may bring food or beverages on board. 

The capacity of our vessels are 6 people MAX (due to coast guard regulations). We do have an option to use two vessels for parties of 7-12; keeping both boats side by side throughout the whole experience. If you have any larger parties than 12 please feel free to send us an email and we can try and accommodate you and your guests.

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½ - Full Day Sail, Snorkel, Kayak, Sunsets

2 to 6 individual passengers or single groups up to 12. Laid back relaxed fun atmosphere. Enjoy our Captained sailing/ snorkeling or sunset Sails, both Bayside & Oceanside. Let 30 years of experience on the reefs and waters around Key Largo set you free to discover. Enjoy the beauty of the Florida Keys.

florida keys sailing tours

Captain Only Charters

Included is a luxury, well-equipped catamaran or monohull with an experienced and professional Captain in charge of the boat and helm. Sit back with a chilled cocktail and experience an unforgettable dream vacation in the beautiful Florida Keys.

florida keys sailing tours

Bareboat Charters

Included Catalina 22’ to a performance ORA design 36’ C&C or Gemini 34’ catamaran, our boats are well-equipped for their chosen usage. Enjoy the freedom of a self-captained vacation. Explore and enjoy sailing in calm, turquoise waters of the Florida Keys.

Own-er-ship in the Florida Keys. What are the benefits:  Tropical, US Waters, 1000’s of miles of shore line, Second Largest Coral Reef in the world, Quick & Easy Access.

Learn to Sail

Learn to Sail or advance your sailing in The Florida Keys. We have an in-house sailing endorsement that teaches you to sail a 22 ft Catalina 22 sailboat or we have the advanced ASA classes from Learn to sail ASA 101 to ASA 120. Why sail in the Florida Keys?

Cottage & Sailboat

Enjoy the beauty of the Florida Keys. Accommodations + Free Sailboats, Kayaks, Canoes, Paddle boards, Fishing/Snorkeling gear and more. All included in a Laid back relaxed fun atmosphere. On the Bayside of Key Largo. Let years of experience around Key Largo Florida set you on a path of discover.

Morning Star Charters, Sailing, Snorkeling, Kayaking, Sunset Sails, Cottages and Sailboat Rentals in the Florida Keys / Key Largo. Sailing and land based Sailing Vacations.

Sailing Charters

florida keys sailing tours

CATAMARAN CHARTERS

Bareboat charters.

  • Fill in our Captain Assessment
  • Once you are approved decide upon a sailing itinerary and submit dates and a float plan
  • Choose how you would like to be responsible for the security deposit.
  • We will then draft up a contract agreement.
  • Choose whether you would like to provision the vessel yourself or have one of our team shop for you for a small additional fee.
  • Confirm snorkel sizes.
  • We will then send you the Leopard manual so that you can read up on your vessel before you arrive.

VESSEL ORIENTATION AND INDUCTION

  • Emergency contacts
  • Emergency procedures
  • Engine operation & maintenance.
  • Generator operation & maintenance
  • Rigging operation, including winches and all lines
  • AC operation 
  • Refrigeration
  • Inverter operations
  • Water tanks and fresh water system
  • Bilge locations and bilge pump operations
  • Stove, barbecue & propane operation
  • Toilets and holding tanks
  • Dinghy and Outboard operations
  • PFD"s, Flares, Firefighting and Man overboard

RETURN DUTIES FOR A BAREBOAT CHARTER

Return inspection.

florida keys sailing tours

HIRE A SKIPPER

If instead you would like to hire a licensed Captain to take the helm during your charter we can help you figure out the credentials they should have and ensure that they are the perfect fit for your vacation. We also have several skippers that we can suggest for your charter and that can competently handle our vessels.

GROUP MONOHULL CHARTERS

The Bloody Pirate is a beautiful schooner sailing in the beautiful Florida Keys. She is named after the famous Code Rum cocktail drink. Enjoy an exciting Keys sailing adventure and watch us hoist her red sails on a true tall ship.. She can accommodate intimate private parties or large groups up to 38 people for day charters or 24 overnight. With her classic lines and open interior you'll feel right at home. Her professional crew will enable you enjoy a relaxing cruise or you may try a real hands-on sailing experience. She is the perfect vessel to take you to the abundance of tropical reefs in the Florida Keys to snorkel and explore. She is particularly suited to large group charters.

PROVISIONING SERVICE

Calypso sailing offers a provisioning service to help get your charter off to a great start. With a little prior organization you can arrive to a vessel that is fully provisioned to your own tastes. We can provide food shopping lists, food and cocktail menus to  ensure that all your necessary and favorite items are all onboard and ready for your charter. We are happy to arrange any of your vacation essentials for you so you don't have to waste valuable vacation time shopping. 

Feel free to contact us about shipping some items to us ahead of time also we will make sure they are waiting onboard for you.

Bareboat Captain Assessment

Bareboat Float Plan

Boating Saftey

305-393-1394

[email protected]

KeyZ Charters

Welcome to KeyZ Charters

Unique florida keys boat charters & boat tours.

KeyZ Charters in Islamorada is the perfect family adventure for exploring the Florida Keys , Everglades National Park , and South Florida. From Islamorada snorkeling and sunset cruises to bird-watching charters, eco-tours, and Florida Keys boat tours, our charters are exhilarating.

Based in South Florida, our boat charters and private boat tours can take you up close to popular Florida landmarks such as Indian Key, Lignumvitae Key , Alligator Reef lighthouse, and Everglades National Park. Whether you like snorkeling, watching the sunset on a boat, bird watching, or relaxing on a sandbar, KeyZ Charters offers private boat tours and private charters that can be customized for any type of adventure.

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Our services, private boat tours & charters in islamorada & florida keys.

Eco-Tours

Discover the natural wonders of the Florida Keys with KeyZ Charters' unforgettable eco-tours in Islamorada . Our knowledgeable guides will take you on an adventure through the crystal-clear waters, lush mangroves, and diverse wildlife habitats. Whether you're interested in birdwatching , spotting dolphins, or simply immersing yourself in the beauty of the Florida Keys, our eco-tours offer a unique and relaxing way to explore this stunning area. 

Snorkeling

KeyZ Charters snorkeling tours in Islamorada take you to some of the best snorkeling locations in the Florida Keys . Our tours are designed for all ages, and our professionally trained guides will give you access to the best sites in the area, including coral reefs and diverse marine life. You may even have the chance to spot manatees or dolphins during your Islamorada snorkeling tour . 

private sunset cruises islamorada

  • Sunset Cruises

A KeyZ Charters sunset cruise is the perfect way to unwind and take in the breathtaking beauty of the Florida Keys . As you sail along the calm waters, you'll enjoy the soothing sound of waves lapping against the boat and the refreshing ocean breeze. Our Islamorada sunset cruises showcase the stunning colors of the sky as the sun dips below the horizon, creating an unforgettable and romantic experience. 

Historic Island Tours

  • Historic Island Tours

KeyZ Charters' historic island tours of Indian Key and Lignumvitae Key , offer a unique way to experience the rich history and natural beauty of Islamorada & the Florida Keys. Explore Indian Key, the first county seat of Monroe County, and discover the fascinating past of this once-thriving community. Your tour also includes a visit to Lignumvitae Key, home to Florida's oldest botanical gardens, showcasing a diverse array of native plants & wildlife. 

Custom Combination Tours

  • Custom Combination Tours

Create your perfect Florida Keys adventure with KeyZ Charters' custom combination boat tours . Our flexible options allow you to mix and match activities to suit your interests and preferences. Combine Islamorada sightseeing, snorkeling , visits to historic islands , and even catching a stunning sunset on a private boat charter . Our experienced team will work with you to create an unforgettable, tailored experience in the beautiful Florida Keys. 

Half day Excursions

Islamorada Half Day Excursions

Make the most of your time in the Florida Keys with KeyZ Charters' 4-hour half-day excursions . Our customizable tours allow you to experience the best of Islamorada by combining activities like snorkeling , eco-touring , and relaxing at a sandbar . Whether you're looking for adventure or relaxation, our half-day excursions offer the perfect blend of activities to suit your preferences. 

Islamorada Sandbar Tours

Islamorada Sandbar Tours

Unwind and enjoy the beauty of the Florida Keys with KeyZ Charters' Islamorada sandbar tours . Our unique experiences take you to pristine sandbars just off the coast of Islamorada, Key Largo, Marathon, and throughout the Florida Keys. Swim in the crystal-clear waters, snorkel among the vibrant marine life, or simply relax and soak up the sun on these stunning sandy oases. Our sandbar tours provide the perfect escape during your Florida Keys vacation. 

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Get in Touch

KeyZ Charters 77522 Overseas Highway Islamorada, FL 33036

Stay Connected

Discover the beauty of the Florida Keys with KeyZ Charters, offering unique boat tours and private charters in Islamorada . Our experienced captains provide unforgettable adventures, from eco-tours and snorkeling to historic island visits and stunning sunset cruises . Explore popular landmarks like Indian Key , Alligator Lighthouse and more aboard our comfortable deck boats. Whether you're interested in Islamorada eco-tours , snorkeling excursions , historic island tours , or Everglades adventures , KeyZ Charters has the perfect trip for you. KeyZ Charters is your gateway to exploring the natural wonders of South Florida. Perfect for families and groups seeking a personalized Florida Keys experience . 

Copyright © 2024 KeyZ Charters · All rights reserved.

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Sail the Florida Keys

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Get Away to Key West and Explore the Florida Keys by Sailboat

Did you know there's an international airport perched out in the Gulf of Mexico at Key West? Serviced by all major US airlines and with frequent flights from main airports in the East and South, Key West is so easy to get to. That's where you'll find our boat charter operators, who have a range of sail and motor boats for you to explore this unique corner of the USA.  

Along the Florida Keys the holidaymaking options are numerous. Enjoy the aquatic environment with countless opportunities to snorkel, swim, kayak, paddleboard and more, while totally relaxing on board, or ashore on one of the Keys' beautiful beaches. Enjoy an evening meal in one of the upmarket restaurants that dot the Keys, shop and enjoy the nightlife in the major centers of population, and get close to nature at one of several locations designated State Parks. 

While pandemic concerns are limiting travel options, consider Key West as your next boat charter vacation destination. Local ordinances reflect the need to keep everyone protected and make this a safe destination. The communities are welcoming and open for business. 

florida keys sailing tours

Some of the highlights to experience on a Florida Keys Sailing Charter Vacation 

Your Florida Keys adventure likely begins and ends at Key West, which is closer to Cuba than Miami yet connected to the US mainland by the 90-mile long Overseas Highway that's an experience in itself. Most sailing charter visitors arrive by air and take the short transfer to one of the charter bases located on the island. Famous for its coral reefs, local architecture, historic sites and nightlife, charming Key West is well worth some time before or after your charter.  

Like most charterers however, you will probably be keen to go sailing and start exploring the chain of cays that make up this most southerly part of the Continental USA. Two great things about sailing here are that distances between attractions can be as short as you'd like them to be, and anchorages are plentiful, if shallow in places. A seven-day charter Key West to Key Largo and return is easily achievable. 

Travelling out of the Stock island marina, it's less than 30 nautical miles to Baihia Honda Key, a popular stopover. In the vicinity there's a variety of stunning beaches, some say the best in the world. Looe Key has some of the best snorkelling you'll experience on your vacation. 

A similar distance to that travelled above will take you from Bahia Honda Key to Long Key, via Marathon, a major sport fishing town of 10,000 people surrounded by the bountiful sea. Stop a while and enjoy a seafood lunch, or you may prefer to do Marathon on the return. At Long Key enjoy the natural surroundings, the greenery and the birdlife. 

Perhaps after two days of sailing that have taken you from Key West more than half way to the mainland, you're ready to take it a bit easier. Less than ten nautical miles onward you'll come to Indian Key Historic State Park at Islamorada. Nearby is the San Pedro Underwater Archeological Preserve, another one of the numerous state parks along the Keys. The San Pedro was a Dutch ship sunk during a hurricane in 1733. What remains lies in 18 feet of water 1.25nm south of Indian Key, easily accessible to good swimmers. 

From Indian Key, it's a further 20nm sailing distance to Key Largo. Apart from the shops, bars and restaurants, most of the attractions are aquatic-based as they are all along the Keys. A visit to the Florida Keys Wild Bird Rehabilitation Center can be rewarding, a reminder of the fragility of nature in this delicate place. 

If you enjoy walking while on vacation, the Florida Keys Overseas Heritage Trail is accessible to many points along your sailing route. 

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We will match any discount website offer on charter boat price, and still provide our customary high level of service.

The Essential Guide to Sailing Holiday Charters

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Boat Tours and Sunset Cruises in Marathon, FL

Explore the Florida Keys Like a Local - On A Boat!

Experience the Keys aboard the brand new Marathon Mermaid! Your next adventure is waiting for you.

Built from the ground up, the “Marathon Mermaid” is truly a one of a kind boat, the only one like it in the world. We offer exciting boat tours for you to see and experience all of the beauty the Keys has to offer! Take in the sunset in style , cruising around the iconic 7 Mile Bridge during our sunset boat cruise, explore our island like a local at the sandbar , or snorkel the famous Florida Keys Sanctuary, or book the entire boat and have an adventure of a lifetime!

  • Most Popular!

Marathon, FL Sunset Cruise

Experience the famous Keys sunsets in style! Come join us for a relaxing evening aboard the Marathon Mermaid while enjoying champagne, music, good times, and incredible sunset views. One of the best ways to experience the Keys!

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Sandbar Experience & Sightseeing Cruise

Have a Fun & Relaxing Day at the Sandbar that’s a go-to spot for the locals ! Let the Marathon Mermaid take you to explore our island, complete with a sightseeing cruise and a fun and relaxing day at the local sandbar.

  • Hour Glass 3 Hours

Reef Snorkel Cruise in Marathon

Come out with us and snorkel the world’s 3rd largest barrier reef! We will take you to the famous Sombrero Key Light Reef on the fastest, newest and most comfortable boat in Marathon!

Hello! Welcome to the Marathon Mermaid! Having a Marathon Florida Boat Tour company has been a dream of John and Angela’s for years, and now is finally a reality! John, born and raised in Marathon, and Angela, a “transplant” from California, met in 2015, when Angela was a scuba instructor at the marina where John owned his rental boat business. Angela had dreamed of owning her own charter boat for years since she became a professional scuba diver and John wanted to be the person to make that dream come true with his skills and knowledge of boats. Skip forward a few years and they started to work on this dream, and that is where the “Marathon Mermaid” was born. Together, John and Angela put both of their ideas together to create this beautiful and unique vessel for some of the best Florida Keys boat tours and cruises in the area.

What Our Customers Have to Say

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What a great experience!!! Will definitely go again when we visit next year!! We did the sandbar excursion and it was well worth the money. The staff was friendly and helpful!!! Highly recommend!!! One of my favorite things we did while visiting!

What a great way to spend the afternoon in Marathon! You get to see the Key and experience getting out on the water. The crew was fantastic and the boat was clean and like new.

The boat and the whole team are fantastic! Highly recommend this as a pivotal Florida experience. I had the pleasure of meeting Angela, one of the owners, while I was there and her kindness and helpfulness were the icing on the cake! Thank you Marathon team!!

We took the Sunset Cruise and it was wonderful! Tropical music, champagne and a sunset,.you can't ask for much more! The crew was excellent and made the trip very enjoyable. This is a truly magical tour and well worth the money!

Reviews frommillions of Tripadvisor travelers place this attraction in the top 10% worldwide.

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Marathon Mermaid

1688 Overseas Highway, Marathon, FL 33050, US

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Fun Activities

Islamorada sandbar only, half day snorkeling/sandbar, large group snorkeling/sandbar, sunset tours, special events, 5-star reviews.

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Contact Information

  • 305-360-1731
  • [email protected]
  • 87200 Overseas Hwy Islamorada FL, 33036

Our Location

Book direct.

Customers will receive a full refund or credit with 24 hours notice of cancellation. Customers will also receive a full refund or credit in case of operator cancellation due to weather or other unforeseen circumstances. Contact us by phone to cancel or inquire about a cancellation. No-shows will be charged the full price.

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florida keys sailing tours

THE 10 BEST Florida Keys Tours & Excursions

Florida keys tours.

  • Sightseeing Tours
  • Walking Tours
  • Ports of Call Tours
  • Up to 1 hour
  • 1 to 4 hours
  • 4 hours to 1 day
  • 5.0 of 5 bubbles
  • 4.0 of 5 bubbles & up
  • 3.0 of 5 bubbles & up
  • 2.0 of 5 bubbles & up
  • Likely to Sell Out
  • Special Offers
  • The ranking of tours, activities, and experiences available on Tripadvisor is determined by several factors including the revenue generated by Tripadvisor from these bookings, the frequency of user clicks, and the volume and quality of customer reviews. Occasionally, newly listed offerings may be prioritized and appear higher in the list. The specific placement of these new listings may vary.

florida keys sailing tours

1. Key Largo Two Reef Snorkel Tour - All Snorkel Equipment Included!

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2. Key West Sunset Sail with Full Bar, Live Music and Hors D'oeuvres

florida keys sailing tours

3. Shark and Wildlife Viewing Adventure in Key West

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4. Mangroves and Manatees - Guided Kayak Eco Tour

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5. Epic Sandbar Safari With Dolphin Playground Encounter In Key West

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6. Key West Sunset Cruise: Dinner and Drinks Included

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7. Florida Keys Reef Snorkel & Sail Adventure

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8. Key West Hop-On Hop-Off Trolley Tour

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9. Key West Small-Group Sunset Sail with Wine

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10. 1 Day Key West Tour from Miami Florida

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11. Key Largo Snorkeling Tour - rental mask, fins and vest INCLUDED

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12. Key Largo Coral Reef Glass Bottom Boat Adventure

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13. Half-Day Cruise from Key West with Kayaking and Snorkeling

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14. Key West Mangrove Kayak Eco Tour

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15. Key West Island Adventure Jet Ski Tour: Bring a Partner for Free

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16. Half Day Snorkel Trip on Reefs in the Florida Keys

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17. Biologist Owned & Operated: Dolphin Watching & Guided Snorkeling

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18. Key West Afternoon Snorkel Sail with Live Music and Cocktails!

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19. Florida Keys Backcountry Eco Tour from Big Pine Key

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20. Key West Day Trip from Miami with Activities

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21. Southernmost Food & Cultural Walking Tour by Key West Food Tours

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22. Key West Half-Day Fishing Tour

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23. Key West Dolphin Watch and Snorkel Cruise

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24. Key West Full-Day Ocean Adventure: Kayak, Snorkel, Sail

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25. Sunset Sail in Key West with Beverages Included

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26. Key West Ghosts and Gravestones Trolley Tour

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27. Fort Lauderdale to Key West Tour with Optional Add-ons

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28. Key West Snorkeling with Breakfast and Unlimited Mimosas

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29. Adults only Sunset Cruise from Key West with Champagne

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30. 2 Location Snorkel Tour - Gear Included, 65 minutes per location

What travelers are saying.

  • Mary M 0 contributions 0 5.0 of 5 bubbles Amazing view even better staff This place is absolutely amazing! All of the staff are incredibly kind specifically Yazmin was so helpful and kind! You can tell they really prioritize personal safety and sustainably for the reef. Amazing place all around and I’ll be using them for all my future trips down to Key Largo and recommending to anyone I know coming to the area. Read more Review of: Key Largo Two Reef Snorkel Tour - All Snorkel Equipment Included! Written May 6, 2024 This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.

sreptile

  • Key West Sunset Sail with Full Bar, Live Music and Hors D'oeuvres
  • Key Largo Two Reef Snorkel Tour - All Snorkel Equipment Included!
  • Key West Mangrove Kayak Eco Tour
  • Shark and Wildlife Viewing Adventure in Key West
  • Key Largo Coral Reef Glass Bottom Boat Adventure
  • Theater of the Sea
  • Dolphins Plus Marine Mammal Responder
  • Dolphins Plus Bayside
  • Key West Extreme Adventures Shark Tours
  • Cruisin' Tikis Key Largo
  • Bluewater Adventure The Keys
  • Islander Girl Snorkel &Tours
  • Marathon Mermaid Charters
  • Sea Horse Private Charters
  • A Family Fun Boat Tour Company
  • Keys Boat Tours
  • Schooner Jolly II Rover
  • Capt. Clint Moore
  • Breezin Sailing Charters

Mike's Sailing Charters 

527 Caribbean Drive. Key Largo, Fl. 33037  MM 100

For reservation:  305.766.7484 or [email protected]

mikessailingcharters.com  

  Mike's Sailing Charters introduce Stiletto Catamaran in the center of the Florida Keys

For familes and small groups, 2 to 6 persons

Departures daily. You decide the time!!

MM 50- Florida Keys 

Snorkel gear and soft drinks included

WORKING WITH PEOPLE NOT NUMBERS

Captain Mike celebrating 20 yrs in Charterboat Service in the Florida Keys.

Sailing experience includes solo Atlantic crossing, Africa, Europe and Caribbean

Mike's Sailing Charters

 35 Sombrero Blvd. Marathon, Fl. 33050  MM 50

mikessailingcharters.com

Florida Yachts Charters Logo

READY. SET. SAIL THE FLORIDA KEYS

At the end of a 110-mile-long chain of islands, stretched like a string of pearls across a Caribbean blue sea lies charmed Key West, it is here you will find Florida Yachts Charters. We are a boutique yacht charter company that specializes in Bareboat and Crewed Charter, ASA Sailing Instruction and Yacht Management. Experience the best of sailing the Florida Keys with a well maintained fleet of yachts, local knowledge and expertise, a warm island welcome and the personal touches of a luxury yacht charter.

Bareboat Charter

Raise the sails or take the throttle. With a bareboat charter i f you have the experience, then enjoy the freedom of captaining your own yacht on your own Florida Keys adventure. Explore our fleet of sailing monohulls, catamarans and power yachts.

Captained Charter

Sit back, relax, and let the professionals do all the work. Charter the yacht of your choice and connect with one of our experienced crew for your carefree sailing vacation in the Florida Keys. Want a full-service chef, we can help with that too!

Learn to Sail

Let us show you the ropes. Do you dream of owning or bareboat chartering your own sailing yacht one day? We are an accredited ASA Sailing School offering fully private courses for high quality one on one time with your instructor. Customize your itinerary and turn your Florida Keys sailing vacation into a great educational opportunity for you and your family.

Yacht Management

If you are dreaming of enjoying the luxury of keeping your yacht in paradise then join our curated fleet of well maintained charter yachts. We will be happy to consult with you about our yacht management options in the Florida Keys.

6651 Maloney Ave, Unit 1 Key West, FL 33040

[email protected] 800-650-6940

KEEP IN TOUCH

Destination and charter fleet updates, special offers, and more

florida keys sailing tours

Florida Keys Sailing

Florida Keys Sailing

Private liveaboard classes, come sail with us.

florida keys sailing tours

Proud Member of the ASA

At Florida Keys Sailing our specialty is: Private Live Aboard Sailing Classes and Sailing Vacations with just you and your spouse or friends. “Learn to Sail” or take an Advanced Class to develop your skills. Qualified sailors can Charter our boats. A Captain will happily take you and your family on a Day Sailing Trip if you need one. Many sailing classes offered elsewhere crowd you on a boat with a group of total strangers.

At Florida Keys Sailing ALL of our Sailing Classes, Day Sailing Trips, and Private Charters are exactly that…PRIVATE.

No one else except YOUR Party is ever on-board. This means you will learn more by having more time DOING, not WATCHING someone else sail. Dollar for dollar you will find more VALUE in taking your Sailing Courses at Florida Keys Sailing.

Or download the form here

Fun on the Waves

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Our Classes

To learn more about the liveaboard classes we offer, visit our classes page

2 DAY BASIC FUNDAMENTALS OF SAILING

Designed for beginners who want the best introduction to the exciting sport of sailing. Students will receive a good understanding of all the “Basic Fundamentals of Sailing”. They will leave as very competent Crew Members.

3 DAY BASIC KEELBOAT “LEARN TO SAIL CLASS”

Beginner students will learn to responsibly be the Skipper of a Day Sailing Keelboat in familiar waters in moderate wind and sea conditions. Classes available are year round on demand based on your travel plans.

5 DAY BASIC COASTAL CRUISING OR 101 & 103

Students will learn to responsibly skipper and crew an auxiliary powered cruising sailboat during daylight hours within sight of land in moderate wind conditions. This Private Live Aboard Class is taught aboard our Catalina 30' or Irwin 34 Offered all year on demand based on your travel plans.

5 DAY BAREBOAT CRUISING OR 103 & 104

Charter a cruising sailboat during daylight hours in most wind and sea conditions. This Private Live Aboard Class is taught aboard our Irwin 34. Offered all year on demand based on your travel plans. 5 Days and 4 Nights…Privately Living aboard at our Dock

3/1 DAY ADVANCED COASTAL CRUISING OR 106

Cruise a sailboat during nighttime hours in most wind and sea conditions. A Private Live Aboard Class is held aboard our Catalina 30 or Irwin 34. Offered all year on demand based on your travel plans. 3 Days and 3 Nights…Privately Living Aboard

7 DAY BAREBOAT CRUISING OR 101, 103 &104

Charter a cruising sailboat during daylight hours in most wind and sea conditions. This Private Live Aboard Class is taught aboard our Irwin 34 This is the Class the Bareboat Charter Companies want you to have. Offered all year long on demand based on your travel plans. 7 Days and 6 Nights…Privately Living Aboard at our Dock

3 DAY FAST TACK TO CRUISING ASA 101 & 103

It’s the fastest and least expensive way to get the first 2 – ASA Certifications. Both combined into a 3 Day / 2 Night Live aboard Class. Prior sailing experience before enrolling is advised. Only $2,039 per student! And better yet…a second student enrolls for FREE!

5 - DAY FAST TACK TO BAREBOAT CRUISING ASA 101, 103 & 104

It’s the fastest and least expensive way to get these 3 - ASA Certifications. All 3 are combined into a 5 Day / 4 Night – Live aboard Class. Prior sailing experience before enrolling is advised. Only $3,599 per student! And better yet…a second student enrolls for FREE!

Testimonials

Daysailing & charters, we offer both daysailing and charters, click below to learn more.

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Sunset Watersports Key West

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Great company with nice equipment and friendly staff we went out to a sandbar and explored around the mangroves

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Heading to the Florida Keys for a quick summer getaway? Here are 10 things to know

Summer vacation is coming up fast. And you might be thinking about a getaway to the Florida Keys.

Special events fill the calendar, giving day-trippers or longer-term visitors more to do than just a bar crawl along Duval Street. Whatever your plans, there’s always the glorious sunsets and the lazy days on the beach.

Here are some helpful things to know about the Florida Keys as you gear up for a spring or summer trip:

1. Upcoming events in the Florida Keys

Key West Pride: June 5-9, Celebrate Pride on a tropical island that is legendary for its laid-back style and its open and accepting atmosphere. For more information, go to gaykeywestfl.com/pride

Lower Keys Chamber of Commerce Dolphin Tournament: June 7-9, largest dolphin wins, so enter for $35,000 in cash and prizes. For registration or more information, go to lowerkeyschamber.com/product/27th-dolphin-tournament/

Hemingway Look-alike Contest: July 17-21 at Sloppy Joe’s in Key West, celebrates author Ernest Hemingway’s life in Key West. For more information, go to keywestlookalikes.com

2. The most notable beaches in the Keys

The Florida Keys aren’t known for the beaches. If you’re imagining an island paradise, you’re in luck. If you’re imagining an island paradise with miles of sandy beaches, you could be disappointed. There are only a few of those accessible by land.

Sombrero Beach: 200 36th St. on the ocean side in the Middle Keys city of Marathon. This is one of the Keys' best-kept secrets. It’s a picturesque sandy beach with crystal-clear shallow water. There’s also playgrounds, restroom facilities and picnic areas.

Anne’s Beach: Mile marker 73 in Lower Matecumbe Key in the Village of Islamorada. Not a traditional beach, but also a hidden treasure in the Keys. The beach has a boardwalk under a mangrove canopy. Instead of setting up a spot on the sand, beachgoers typically pitch their chairs in the shallow clear blue water and laze the day away. Restrooms are in the small parking lot, and picnic tables are on the boardwalk.

Bahia Honda State Park: 36850 Overseas Hwy. at mile marker 37 in Big Pine Key. Like Anne’s Beach, Bahia Honda is a palm tree-lined beach with clear turquoise water. But it’s a lot bigger, with three stretches of beach. Beachgoers can also rent kayaks and snorkeling gear.

Harry Harris Park: 50 E Beach Road, mile marker 92.5, in Tavernier in the Upper Keys between Key Largo and Islamorada. The oceanfront county park has a small, family friendly beach, playgrounds and picnic pavilions.

Curry Hammock State Park: 56200 Overseas Highway at mile marker 56.2 in Marathon. The park has a 1,200-foot-wide sandy beach, picnic facilities and a playground. It is a hot spot for kiteboarders and those who want to sit back on the sand and watch the high-flying action.

Clarence S. Higgs Memorial Beach: 1000 Atlantic Blvd. in Key West.

3. Are there tolls on the Overseas Highway?

No tolls: Traveling on the Overseas Highway is toll-free.

4. Are there tolls on Card Sound Road?

Toll: Card Sound Road, considered an alternate road to the Keys, has a $2 toll, taken electronically through SunPass, at the northern end of the bridge, a 65-foot high, 2,800-foot long span that crosses Card Sound. The cost for toll-by-plate is $3

Directions: Getting into the Keys using Card Sound Road, or County Road 905A, drivers take the highway southeast, over the bridge to a three-way stop sign. If you make a left, you’ll head to the ultra-exclusive gated community of Ocean Reef. Turn right on County Road 905 (without the “A”) and you’re on your way to Key Largo.

5. How long will it take to reach your Keys destination?

Traffic congestion in the Keys — especially during weekends, special events, spring break and the peak tourist season — can slow things considerably. Passing is allowed only in certain spots. Most of the Overseas Highway runs two lanes.

Here are some estimates for your trip:

Miami to Key Largo: The trip can take 2 1/2 hours.

Key Largo to Key West: The trip can take 2 1/2 hours.

Miami to Key West: It’s about a four-hour drive from Miami to Key West, and under three hours from Florida City to Key West without delays.

6. What to know about US 1 in the Florida Keys

Length: The highway runs 113 miles through the Keys over the Atlantic Ocean, Florida Bay and the Gulf of Mexico.

Mile markers: Green mile marker signs are on the side of the road and are used for addresses and directions. The road begins and ends in Key West, where the mile marker zero signs are at Whitehead and Fleming streets.

Bridges: The longest span is the Seven Mile Bridge, which is actually 6.79 miles long. The second longest is the Long Key Bridge, at 2.3 miles.

7. How to monitor traffic to and from the Florida Keys

Two free apps can help you navigate the Overseas Highway. One is for traffic and the other is a guide to the Keys.

—The Monroe County Sheriff’s Office has a namesake app that is a must-have for people who must take the road regularly. The app has a “live calls and traffic info” tab that gives the location and times of crashes or other traffic disruptions, such as when a medical helicopter is landing on the highway. You can also sign up for notifications, which will tell you when lanes are reopened. The sheriff’s office also posts about crashes in real time on its Facebook and Twitter feeds, which you can access through the app.

— A travel app from the Monroe County Tourist Development Council — The Florida Keys and Key West — features just about everything you want to know about exploring the islands. The app includes narrated driving tours — one for each direction of the highway — along with lists of hotels, restaurants, art galleries, watersports rentals and fishing guides. Information is categorized by location: Key West, the Lower Keys, Marathon, Islamorada and Key West. The app also has videos of the Keys, a map and weather forecasts.

Both apps are available through the Apple Store and Google Play.

8. What if you get seriously sick during your visit?

Monroe County has three hospitals, with one marking each major section of the island chain from Key Largo to Key West.

For major traumas, patients are airlifted by helicopter to medical centers in the Miami area.

Addresses and phone numbers for the hospitals are listed below, but if you have a medical emergency, call 911.

Lower Keys Medical Center: 5900 College Rd. Key West, 305-294-5531. Key West’s Lower Keys Medical Center has 167 beds spread over two locations. The main campus with an emergency room is on College Road on Stock Island. The hospital has 23 beds at its DePoo Medical Building, 1200 Kennedy Dr., where mental health and rehabilitation services are offered. The number at DePoo is 305-294-5535.

Fishermen’s Hospital: 3301 Overseas Hwy., Marathon, 305-434-1000. This hospital is in the Middle Keys city of Marathon and run by the nonprofit Baptist Health South Florida. The entirely new 33,330-square foot, 22-bed hospital opened last year after the original 1962-era hospital was severely damaged by Hurricane Irma in 2017. Fishermen’s, which is now designed to withstand the wind speeds of a Category 5 hurricane, offers specialized services such as 24/7 emergency care with nine emergency department beds.

Mariners Hospital: 91500 Overseas Hwy., Tavernier, 305-434-3000 In the Upper Keys, Mariners Hospital is a 25-bed hospital run by Baptist Health South Florida. Mariners dates back to 1962. It’s home to the only hospital-based hyperbaric chamber in the Keys. It uses oxygen therapy to treat illnesses that include diving-related decompression sickness.

9. What about urgent care in the Keys or house or hotel visits?

Upper Keys Advanced Urgent Care of the Florida Keys: 100460 Overseas Hwy., mile marker 100.5, Key Largo, 305-294-0011 ext. 2. Monday-Friday 9 a.m. to 5 p.m. Saturdays 9 a.m. to 3 p.m.

Middle Keys Advanced Urgent Care of the Florida Keys: 13365 Overseas Hwy., Suite 102, Marathon, 305-294-0011 ext. 3. Monday-Friday 9 a.m. to 5 p.m. Saturdays 9 a.m. to 3 p.m. With three locations in the Keys, this center treats a range of health problems. The list includes colds and coughs, ear and eye infections, insect bites, minor burns, asthma, cuts, sprains, fractures and chest pain. They also offer various lab and diagnostic tests such as CT scans, ultrasounds and X-rays.

Lower Keys Advanced Urgent Care of the Florida Keys: 1980 N. Roosevelt Blvd. in Key West, 305-294-0011 ext .1. 8 a.m. to 5:30 p.m. This urgent care center has three locations in the Keys.

Key West Urgent Care and Family Doctor: 1501 Government Rd. in Key West. Weekdays 8 a.m. to 4 p.m. Closed Saturdays and Sundays. 305-295-7550. Key West Urgent Care and Family Doctor offers medical care for minor accidents and procedures, along with treatment for colds, flu, sore throat, eye, ear and skin infections and headaches. They also offer lab draws and vaccines for tetanus and hepatitis B and flu shots, along with annual physicals and other primary care services.

Marquesa Medical: 305-504-5611, [email protected]. Amanda Tutlewski, a family nurse practitioner, says she opened Marquesa Medical to offer affordable and convenient healthcare for residents and visitors to the Keys. This practice only makes house calls. She keeps regular hours Monday through Thursday from 4 to 6 p.m. and Fridays from 9 a.m. to 4 p.m. Appointments after hours and on holidays may be available for an additional fee.

10. If you have a hangover in the Keys

Hydration therapy: If you’re sick from a hangover after overdoing it with booze on Duval Street, several places offer “hydration therapy.” This means an intravenous shot of fluids and vitamins. These aren’t emergency medical centers. They are run under the direction of a licensed physician.

In Key West, several businesses, including spas, offer various IV cocktails. Some are mobile and will come to you. Their services are also marketed for those smarting from sunburns, down with migraines or recovering from a marathon run. Prices and lengths of services vary. But expect to spend about $150, or possibly more, and at least 30 minutes for the hangover helper.

Hangover Hospital: 305-912-4911 Hangover Hospital’s IV menu includes hangover packages such as the Code Blue and the Lazarus, which promises to take you “from deathbed to remission in 45 minutes.” Call for appointments. They’ll come to you at no extra cost.

IVs in the Keys Key West: 531 Whitehead St., 305-395-8245. IV in the Keys describes itself as a modern wellness spa.

Summer Breeze Health and Hydration: 335 Duval St. Key West, 305-317-8595.

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    Lower Keys Advanced Urgent Care of the Florida Keys: 1980 N. Roosevelt Blvd. in Key West, 305-294-0011 ext .1. 8 a.m. to 5:30 p.m. This urgent care center has three locations in the Keys.