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Sebago Watersports

• 205 Elizabeth Street Key West Florida 33040
• 8:00am-8:00pm Open daily 365 days year!
• 305-294-5687
• [email protected]
• https://keywestsebago.com/

Sunset Sails

Parasailing, special events.

• Key West Private Charters

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For over 25 years, Sebago Watersports has delighted guests on Key West’s pristine waters. We take great pride in being Key West’s favorite on-the-water tour company sailing the island’s only fleet of both modern sail catamarans and historic tall-ship schooners. Share a romantic sunset sail, snorkel the reef, or spend a full day of family fun on one of our power or eco adventures. It’s simple… Sebago offers the best tours at a great value. Our food is prepared fresh in our own catering kitchen. Our crew is friendly and highly-trained. Every one of our ships has sails. And we never compromise on our ships or safety.

5 sunset sails to choose from! Our Catamaran Champagne Sunset Sail offers an incredible value and includes all of your beverages. The Schooner and Windjammer Sunset Sails provide a true tall-ship sailing experience with complimentary fruit and cheese, along with premium beverages. Our all-inclusive Land’s End and Captain’s Choice Sunset Sails go all out with a selection of appetizers including peel-n-eat shrimp, premium beverages, and cocktails from our bar, all included.

Snorkeling Excursions

Sebago is the best way to spend a half-day at the reef. Choose from our morning, afternoon, or combo snorkel/sunset sail. All of our snorkel tours include your equipment, professional instruction, and complimentary beverages. Whether you’re a beginner or seasoned snorkeler, you’ll welcome Sebago’s “stairway to the sea” for easy access to the water. Snorkeling is also featured on each of our all-day adventures.

All-Day Adventures

For a truly special day on the water join Sebago for one of our famous all-day adventures. The Power Adventure gives guests a chance to experience it all – snorkel, jet-ski, parasail, kayak, paddle-board, and more. Our Island ‘Ting and Bugeye Backcountry Eco Adventures take guests both snorkeling and into the mangrove ecosystem on kayak outings. All-day adventures are also all-inclusive. Breakfast, Lunch, Snacks, a full selection of beverages, all of the activities, equipment, and instruction are included in one low price.

Soar high above Key West on Sebago’s parasail experience. Parasailing is included in our Power Adventure activities. You can also book a time on one of our daily parasailing trips.

Throughout the year Sebago provides guests the opportunity to take part in several Key West special events. Help hoist the sails in a historic wrecker’s race, view the action of the world power boat racing championship, or watch July 4th fireworks light up our island.

Private Charters

All boats in Sebago’s fleet are available for private charters with each trip fully customized to your specifications, including beverages and delicious catering from Sebago’s kitchen. Perfect for wedding ceremonies & receptions, birthdays, corporate events, family reunions and more!

Tour Pricing

• All day- 165.95
• Snorkel- $39.95 – $49.95
• Sunset sail- $49.95 – $79.95
• Schooners- $49.95 – $99.95
• Parasailing- $69.95 – $169.95
• Eco-tours- $109.95 – $119.95

Browse all Sebago Watersports Tours on our site .

Sebago Watersports is a Key West family-owned and operated business, proud to be the longest established day-charter catamaran operation in the continental United States. We treat each of our guests as a valued customer and member of the Sebago family.

All of our tours provide a premium experience at a competitive price. Sebago chooses to limit the number of passengers on our ships to give you more room to spread out. Sebago’s catamarans and schooners provide an authentic sailing experience with all the amenities that our guests expect: wide decks, generous seating and heads (bathrooms).

When You Book Direct With Sebago: GUARANTEED BEST PRICE EASY CANCELLATIONS BAD WEATHER REFUNDS NO HIDDEN BOOKING FEES

Go to our website for online reservations or call us now at 305-676-8017 .

To receive our Quarterly Newsletter with information on the many fun things to do and see in Key West, special discounts and more, please register below.

Key West Sailing & Cruises

Sebago watersports.

205 Elizabeth St, Key West, FL 33040

(305) 203-5403

Website Tickets

Sebago Watersports in Key West offers a variety of activities that cater to different interests, providing an exciting and diverse experience for visitors. One of the highlights is their sunset sails, which are a quintessential Key West experience. They offer sails on catamarans like the Sebago Flyer or Sebago Cubed, providing a picturesque setting with drinks like champagne, wine, and sangria included. The tours depart daily, with times varying depending on the season​​​​.

For those interested in marine life and adventure, Sebago Watersports provides a range of options. Their snorkeling tours take you to the Florida Keys Reef, where you can swim in warm tropical waters and explore the vibrant marine ecosystem. The tours include all necessary equipment and instruction, and they ensure a comfortable experience by limiting the number of passengers​​.

Another unique offering is the Island 'Ting Eco Tour, which combines sailing, snorkeling, and a kayak tour of the mangroves. This tour includes a continental breakfast, full lunch, and afternoon snack, along with beverages, providing a full-day adventure​​.

For those interested in wildlife, the Captain's Choice Dolphin Watch & Sunset Sail is an exciting option. While a dolphin sighting isn't guaranteed, the tour has a high success rate due to the non-migratory nature of dolphins in Key West waters. This 2.5-hour sail includes a selection of tapas and drinks, creating a relaxing and enjoyable experience​​.

The Catamaran Champagne Sunset Sail offers a luxurious experience with a sail past local landmarks while enjoying the famous Key West sunset. The tour includes champagne, sangria, wine, beer, and soft drinks, making it a perfect way to end the day​​.

These offerings from Sebago Watersports provide a comprehensive way to experience the natural beauty and unique culture of Key West, whether through relaxation or adventure.

Our Little Lifestyle

Family Travel + Airbnb Hosting Blog

Sebago Key West: Sunset Cruise & Snorkeling Sail

We may earn money or products from the companies mentioned in this post. As an Amazon Associate, I earn from qualifying purchases.

If you have been reading our blog for a while, you know that we love being out on the water! Whenever we travel, we always look for outings that do just that, from canoeing the springs to sailing at sunset. Typically, we do these outings as a family or Matt and I as a couple. But, even though I visited Key West solo on this last trip, I still chose to go on a couple of outings myself! In May, I was hosted by our friends at Red Hospitality on a couple of sailings aboard the beautiful Marquesa with Sebago Watersports. And I loved both! Today, I want to share more about our  Sebago Key West Sunset Cruise and Snorkeling Sail.

Sebago Watersports Key West

A long-time favorite by locals and tourists alike,  Sebago Watersports  has been a much-loved Key West fixture since 1988.  

According to their website, they are the longest-established day-charter catamaran operation in the continental United States. They offer a variety of full-day or partial-day outings and really have something for everyone, including a Backcountry  Kayak Tour  and a  Champagne Sunset Sail.   

Their fleet is centrally located in the historic seaport of Key West, making it easy to hop on a boat or two during your visit to Key West. In fact, Sebago Watersports was located right next door to my hotel –  The Marker Key West!

Sebago is proud to have recently been voted one of TripAdvisor’s Top 10% of attractions worldwide. I will let their five-star ratings across the board speak for themselves. 

However, I can speak for myself and had a wonderful time on my outings with  Sebago . The boats were clean, the staff was friendly, it never felt overcrowded, and I loved chatting with the captain. He lives on his own sailboat not too far away and rides his dinghy to work daily! And while it sounds romantic, the work is hard, and the ebb and flow capture the essence of Key West .

Sebago Key West Location

Sebago Key West is located at 205 Elizabeth Street.  Key West, FL 33040, along what is typically referred to as Fisherman’s Alley.  The main office and shop are actually on Lazy Way Lane, between  William and Elizabeth Streets.  However, they have a kiosk located just across the walkway that is typically where you check in.

It is here where their fleet of boats is usually docked and where most of the Sebago catamaran tours leave from.  

What type of outings does Sebago Watersports offer?

In just a minute, I am going to share everything you need to know about the two outings that I did with Sebago Key West  (sunset cruise & snorkel tour), but I just want to share links to a few of their other outings because there are ALL something that I would like to do on future visits, especially if I have the kids with me! 

I know that they would love to try the Parasailing and the Sebago All Day Watersports Adventure , which includes jetskis, banana boat rides, water trampolines, kayaking, and parasailing.

They have a pretty big fleet of boats, including the Marquesa, a 69′ catamaran with over 2300 sq ft of deck space.  Some of the other tours are aboard either the  Sebago Flyer or Sebago Cubed, both 60′ catamarans.   You can also adventure aboard a schooner, jet ski, kayak the mangroves, and more.  Most of the outings include food made fresh daily and drinks.

For Daytime Adventures, Sebago Watersports Key West Offers:

Sebago watersports all day adventure.

This 6-hour outing includes a catamaran sail, jet skis, kayaks, parasailing, banana boat, and floating waterpark, and includes breakfast, lunch, snacks, and all beverages.   This truly is a great value, especially with the food included, because vacation meals add up!  And it even includes beer and wine after the watersports are finished!  Just typing this out has me sold on THIS one being at the top of my list on my next trip to Key West, Florida!

Island Ting Eco Tour

This is also a 6-hour tour and combines three of Sebago’s most popular activities – sailing, snorkeling, and kayaking through the mangroves.  It departs at 9:30 a.m. each day and also includes breakfast, lunch, and a snack, as well as soft drinks and water.  And just like the previous tour, beer, wine, and sangria are offered complimentary once the water sports are finished.

Sebago Backcountry Eco Tour 

This tour is pretty unique because you get to sail aboard Sebago’s 65′ schooner – the Appledore Star!  On this 5 hour tour, you also get to snorkel along reefs and kayak through the mangroves.  A full buffet-style lunch is included, as are drinks, non-alcoholic all day, and sangria, beer, and wine after snorkeling wraps up.

Windjammer Classic Day Sail

Hop aboard Sebago’s two-masted 86′ windjammer – the Appledore II, and cruise the open seas! This outing does not involve getting into the water (snorkeling, etc.) like the others and is great for visitors who just want to get out there and feel the wind in their hair.  Who knows, you may even get a turn at the wheel or take part in hoisting the sails. This quick 2-hour afternoon sail does include complimentary drinks, including their popular sangria, premium wine, and beer, a full bar, soft drinks, and water.

Parasailing

Available for children 6 and up, these tours leave every hour and are sure to give you an incredible view of the island!

3-Hour Key West Reef Snorkel Morning /  3-Hour Key West Reef Snorkel Afternoon

I did this Key West snorkel trip , the afternoon option, on my last day, and you have to see this Instagram Reel that I made from the water!  I saw all kinds of fish, the weather water perfect and I highly recommend this one.  And keep reading because I will share more info and a lot more photos soon!

For Evening Sailing Sebago Key West Offers:

Captain’s choice dolphin watch & sunset sail.

This is a more intimate two-and-a-half-hour open water sailing that includes appetizers and drinks, too — including premium wines and champagne.  One difference here is that this one does not include food, whereas some of the others do.  This is a great option if you already have dinner plans following your cruise.

Catamaran Champange Sunset Sail

This 90-minute sailing offers complimentary champagne, wine, sangria, chilled beers, and soft drinks.  Plus, some of the best sunsets in the world!

Schooner Champagne Sunset Sail

Similar to the other sailings in this category, this is also a sunset cruise. However, this is the only one offered aboard a schooner!  It is 2 hours in length and also includes appetizers and drinks.  With only 22 guests, this is a more intimate setting than you get aboard the larger catamarans.

Windjammer Classic Sunset Sail

This evening cruise is also aboard a schooner, and it’s the larger of the two.  This one holds over twice as many passengers (49) and also includes all of the drinks.

Lands End Key West Sunset Sail 

I had the pleasure of enjoying the Lands End Sunset Sail, and I loved that it has live music!  The snacks, including the shrimp cocktail, were perfect, drinks included, and it was exactly what I was looking for.  I’ll tell you all about it now!

My Sebago Key West Sunset Cruise

The Lands End Sunset Sail aboard the 69″ Marquesa is such a perfect way to spend an evening in Key West, Florida.  Even better,  I boarded literally steps from my hotel, which made it so convenient.

And I think this is the best deal for a Key West Sunset Cruise !  This two-hour sunset cruise featured live music (that was really good), appetizers (including shrimp),  unlimited wine, beer, liquor, soft drinks, and more!  Plus, you can upgrade to the premium bar for just $9.95, which gives you access to brands like Titos, Captain Morgan, Bacardi, Tanqueray, Wild Turkey, and more.   So, basically, it’s dinner, drinks, and entertainment, all while you literally sail off into the sunset.   Just a night out typically would cost more than that.

For me, it’s the sailing that I love, but the icing on the cake was being able to catch a beautiful Key West sunset.  The sunsets there hit differently.  When you can get out on the open water like this, the sun seems to almost melt into the water, like ice cream over a cone on a hot summer day.

If you have never experienced a sunset out on the water like this, add it to your bucket list! Actually, I am pretty confident that Key West should be on everyone’s bucket list, so just don’t forget to book a cruise with Sebago while you are there!

Here are a handful of photos from my sunset cruise to enjoy before I chat about my snorkel sail!

My Sebago Key West Snorkel Sail

The day following my sunset cruise, I slept in, went to visit the Truman Little White House , and then came back just in time to grab a quick bite at my hotel ( The Marker Key West ) before walking across the street to board the boat.  To say that I didn’t waste a single minute of this trip would be an understatement!

The Sebago Watersports Snorkel Sail can be booked either for the morning or the afternoon, and I opted for the afternoon, leaving at 12:30 p.m.   On this three-hour tour, you’ll see the water running, heading out 7 miles to the Florida Keys Reef.  This is a perfect location for snorkelers, both experienced and novice.  The water was pretty calm and clear when we were there, and we saw a LOT of fish! 

So, if your kids are looking for Nemo, there is a good chance that you’ll be able to find him out there in the blue Caribbean waters.

So, here are some more photos from my Sebago Key West Snorkeling trip!

Planning Your Next Adventure With Sebago Key West

If you are inspired to book your own adventure with Sebago Watersports in Key West, Florida, my best tip is just to browse their website.  It is very easy to navigate, and you can check rates and coordinate availability with your itinerary.   

And at Sebago Watersports, they like to think of you as family, so once you adventure with them once, they like to send you special offers that were almost tempting enough for me to extend my trip another day!

Also, the Sebago website has a great FAQ section, and while I can share my thoughts and a bunch of pretty photos here, you’ll want to go there for full details,  more in-depth answers to your questions, trip planning, and the like.   And you always get the best prices when booking online!  It should be smooth sailing from there.  Ok, I couldn’t resist throwing another pun in there.

Happy traveling, and if you get a chance to sail with Sebago, leave me a comment and let me know what you think!

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Last Updated on January 13, 2024 by Sarah

Water Sports

Sebago watersports.

205 Elizabeth St, Key West, FL 33040

(305) 203-5403

Website Tickets

Sebago Watersports is a leading watersports company based in Key West, offering a variety of maritime activities. The company provides catamaran and schooner sailing tours during both sunset and daytime. Sebago is especially renowned for its sunset sails, with spacious 60-foot sailing catamarans providing guests with a breathtaking view of Key West's famous sunsets while enjoying complimentary drinks. In addition, the company offers parasailing services, allowing visitors to experience the thrill of soaring high above the Caribbean waters while enjoying spectacular views of the island and marine life. Snorkeling tours are also a key attraction, offering participants a chance to swim in warm, tropical waters and explore the colorful marine life of the Florida Keys Reef. Furthermore, Sebago's all-day adventure is perfect for families and large groups, providing a full day of fun in the sun with activities like snorkeling, jet skiing, kayaking, and paddle-boarding. This package also includes meals and beverages, with no additional charges. Every trip departs from Key West's Historic Seaport and provides an authentic sailing experience.

Insider Picks For The Best Tours & Activities To Choose From In Key West!

Time For Vacation In Key West!

Hand Selected 5-Star Activities In Key West, Florida

I'm On Vacation In Key West!

Let the adventures begin.

What type of tour are you looking for? Browse through our categories to find your perfect adventure!

Sails and Cruises

Fun Filled Watersports

A Little Bit About Us

We are residents of Key West and have experienced all there is to see and do on our little island paradise!  We welcome you to Key West and are excited to share the best of the best in activities and tours.  We have experienced all activities and tours on our site and have hand selected the best 5-star experiences for you to choose from.  Book online or call us for more information on any of the tours, we are happy to help! We look forward to seeing you!

Our Most Popular Tours

CATAMARAN CHAMPAGNE SUNSET SAIL

• Adult from $44.95
• Age 4-11: $29.95

Key West is known for its world famous sunsets. The local way to experience one is with Sebago. Let us make your Key West vacation complete with a sunset sail on Sebago Flyer or Sebago Cubed, our 60′ sailing catamarans with plenty of room to stretch out and enjoy the breathtaking view.

KEY WEST REEF SNORKEL – MORNING

• Adult from $39.95

Start your morning right on a sailing catamaran with a reef snorkel. Picture yourself swimming in warm tropical waters surrounded by colorful fishes. Seven miles off Key West’s coast lies the Florida Keys Reef with shallow, Caribbean waters perfect for easy snorkeling.

PARASAILING – KEY WEST

• Every Hour on the Hour
• Adult from $59.95
• Age 6-11: $59.95

For the best parasailing in Key West, let Sebago get you airborne! Key West is an awesome place to parasail with its gentle, warm winds and clear Caribbean waters. From high in the sky, you can see the entire island and gain a whole new perspective on island living.

ISLAND ‘TING ECO TOUR

• Adult from $99.95
• Age 0-11: $79.95

Sebago’s Island ‘Ting Eco Tour combines 3 great Key West adventures into one: Key West sail cruise, snorkel the coral reef and kayak tour of the mangroves, all in one day. Save money and time by experiencing Key West’s favorite activities in one awesome tour.

Family Fun day!

Such a fun way to spend time in Key West. We discover so many things together. They experience was great for youngsters and teens at the same too!time. So many beautiful sights. We were thrilled with the ride the crew was wonderful.

Would Go Again!

Great time. Great boat. Wonderful and knowledgeable staff. Fair price. Happy we didn’t do the short snorkeling trip that was cheap because they were packed in like sardines. Having less people and room to stretch out was worth the extra money.

Excellent Experience Snorkeling!

We had an excellent time on the 1/2 day snorkeling trip. Mitch and his crew were awesome and really took the time to inform everyone about safety procedures and tips for successful snorkeling. We saw a stingray, some barracuda and several other species of fish. Highly recommended!

Fun Times For Everyone!

Looking for a romantic sunset cruise?…we have you covered! Traveling with the family, be sure to check out the All-Day Watersports Adventure!  Love exploring our undersea wildlife?…our snorkeling and eco-tours are perfect for you! Looking to hook the next big fish?…check out our 1/2 and full-day fishing options.

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The Fascinating History of Key West, Florida

We may earn money or products from the companies mentioned in this post. As an Amazon Associate, I earn from qualifying purchases.

As you know, I absolutely love visiting Key West! I’m happiest when soaking in the city’s tropical vibes, listening to Jimmy Buffett songs, and feeling the stress melt beneath the country’s southernmost sunset.  Key West  has a special place in many people’s hearts as a city for misfits, a place for big dreamers who want solitude and freedom. But how did it come to be? Let’s dive into the history of Key West, Florida. 

The History Of Key West

The city has a wild history filled with stories of adventure, mystery, and comedy. Key West’s history has made it one of the world’s most famous island tourist destinations, and its colorful people continue the long tradition of fun in the sun.

As they say, Key West isn’t so much a place as a mindset.  

Historical & Fun Facts About Key West

In this post, I want to highlight some of the more fascinating facts about the history of Key West. I’m touching on lesser-known facts you may not already know. Trust me, there are a lot of them hidden in this eccentric paradise!

And knowing all of these great tropical tidbits of information will ensure you appreciate this charming community on your next trip! 

Key West Was Originally Called “Bone Island”

An obscure fact about  Key West  is that centuries ago, it was called “Bone Island.” The ancient fishermen visiting the island found large amounts of human remains there. It turns out that ancient indigenous peoples used the island as a communal burial site.

The Island Was Sold Twice

It’s true! In 1790, Spaniard Don Juan de Estrada received the island through a land grant from the Spanish government. He then sold it to Juan Pablo Salas in 1815.  

Salas was so excited to make a profit on the island that he sold it twice! First, to John Simonton, for $2,000 in 1821. And second, in 1822, to an attorney named John Strong. It took many years for ownership to get straightened out, and Simonton was declared the rightful owner in 1828.

Only One Of Key West’s Founding Fathers Lived There

Of the four founding fathers heralded as the original settlers and developers of the city, only one spent a significant amount of time living there. Pardon C. Green lived permanently on the island in the early and mid-19th century. While in Key West, he started a company, was a city council member, and briefly served as mayor.

Key West Is One Of The Warmest Places in The Country

Key West, Florida, is the southernmost point in the United States. You can see a famous bright red buoy marking this point at the corner of South and Whitehead Streets.  

It’s one of the sunniest and warmest places in the US, with 260 annual sunny days and temps ranging from 65°F to 89°F. Key West also has the warmest ocean water of any place in the United States in the winter and averages 75°F to 77°F.

Key West Is Near A Giant Barrier Reef

Key West sits on the only living coral barrier reef in the US. Several related reefs extend 350 miles from the Dry Tortugas west of Key West to the St. Lucie Inlet near Miami. Coral reefs are home to many marine life and a unique underwater ecology. Almost 1,400 species of aquatic plants and animals live in the Florida Reef.

Key West Is Closer to Havana than Miami

Key West  is closer to Havan, the capital of Cuba, than Miami, Florida. Key West is so far south in Florida that it’s very close to Cuba, which lies only 95 miles off-shore. Due to their proximity, Key West and Cuba often share common elements of their culture, people, and economy.  

Ernest Hemingway Loved Key West

The Nobel Prize-winning author Ernest Hemingway lived on the island during the middle of the 20th century. You can still tour his home and see his amazing six-toed cats. They all descend from “Snow White,” a six-toed cat Hemingway received as a gift. The cats have a genetic mutation that gives some cats six or more toes! This trait is reliably passed down to each generation of newborn kitties.  

At the Hemingway House, you can also see the penny he placed in the wet cement of his pool. It was the first pool built in a 100-mile radius and was so expensive he put the penny there and exclaimed, “You can take my last penny!’ when he saw the construction bill.  

I love reading about the history of Key West as it relates to Hemingway!

A Lot Of Famous People Have Lived In Key West

For a small town with a population of only 26,000,  Key West  boasts an astounding number of famous inhabitants over the years.  They all contributed to the history of Key West in one way or another!

A short list includes author Judy Blume, poet Wallace Stevens, author Shel Silverstein, playwright Tennessee Williams, President Harry S. Truman, author Earnest Hemingway, singer Jimmy Buffet, NASCAR Driver Dale Earnhardt Jr., poet Robert Frost, author Truman Capote, fashion designer Calvin Klein, and treasure hunter Mel Fisher.

Key Lime Pie Was Invented In Key West

Was Key Lime Pie first made in Key West? Legend has it that in the late 1800s, Key West sponge fishermen called “Hookers” would make homemade food by pouring sweetened condensed milk with lime juice over Cuban bread. Wives of these men began baking it into a pie crust to create a sweet dessert.  

Sarah Jane Lowe Curry, the daughter-in-law (other legends say she was his cook) of Florida’s first millionaire, started serving the dish to people who came to her house. Sarah, or “Aunt Sally” as she was known, became the mother of the Key Lime Pie. Soon after, the pie was being served in restaurants everywhere.  

Whether or not you believe these stories, the truth is that Key Lime Pie is a famous Key West dessert, and you can find these delicious pies served at many of the city’s restaurants.

Chickens Walk The Streets of Key West

Yes, Key West has a lot of chickens wandering around the city! Chickens are the original inhabitants of the keys. Early locals lived alongside them and raised them for eggs or meat.  

The ancestors of these birds have become the official Key West Gypsy chickens, and they proudly and unabashedly prowl the streets of  Key West . Seeing these fowl reminded me of Ybor City and their resident chickens!  

In 2004, the city hired a professional bird catcher. But, the citizens did not receive it well, and the position was eventually eliminated. Now, you can enjoy the Gypsy chickens, and they get to live a peaceful life as a tourist attraction in one of the nation’s top vacation destinations!

Key West Is The Birthplace of Pan Am Airlines

Pan American Airlines started in Key West, Florida, in 1927. The location is now home to First Flight, a restaurant and bar. But the aviation history of Key West doesn’t stop there!

Known as The Amazing Race, in 1913, a competition started between two early aviators to see who could make the first flight from Key West to Havana, Cuba.

Then, in 1920, Aeromarine Airlines flew America’s first official international airmail service, once again between Key West and Havana.

President Truman Made A “Little White House” in Key West

In 1946, President Harry S. Truman began using a home in Key West as a winter retreat and operated it as a remote “White House .” He stayed in the home intermittently for 175 days over 11 visits. This house had earlier famous visitors, including President William Taft and Thomas Edison.  

Today, the home is the Harry S. Truman Little White House. It’s Florida’s only presidential museum. At the museum, you can tour the home, see Presidential memorabilia and photos, and learn the history of Truman’s presidency and its importance to Key West. The house is set within a beautiful botanical garden filled with tropical flora.  

I visited the museum, and I highly recommend it! Not only did we learn about President Truman while on the tour, but we also learned a great deal about the history of Key West.

Key West Loves To Celebrate

For a small island,  Key West  has a tremendous capacity to party! It’s known for several famous annual festivals that attract people from all over the world.  

The Conch Republic Independence Celebration (April 20-29, 2024) starts with a conch-blowing contest. It continues with boat races, a parade on Duval St, victory pirates, and a Pirates Ball and Costume competition.  

The Key West Songwriters Festival (May 1-5, 2024) showcases veteran and new songwriters who take the stage to mesmerize audiences with music and storytelling. Household names like Kacey Musgraves and Florida Georgia Line got their start here.  

Hemingway Days (July 17-20, 2024) honors the giant legacy of author Ernest Hemingway by doing something he did best: celebrating. The festival includes presentations by Hemingway scholars, appearances by Hemighway family members, and an awesome look-a-like contest where hundreds of white-bearded, swarthy men channel their inner “Papa.”

Fantasy Fest (October 18-27, 2024), which started as a costumed parade down Duval Street, has grown into 10 days of parades, parties, street fairs, and fantastical balls. Most of these activities are not for kids. Adults might have fun at the “naughty” bike rides, pajama parties, and burlesque shows across the city. So, if you are visiting Key West with kids, avoid that week! 

Key West Has Many Famous Buildings

Key West is filled with buildings with an intriguing history. Aside from the more popular places like the Hemingway House and the Truman Little White House, several other famous buildings exist.  

The Audubon Hosue and Tropical Gardens showcases works from the ornithologist John James Audobon. Audubon drew 18 new birds after having visited Key West. You can explore the house and its 1-acre surrounding gardens.  

The Basilica of St. Mary Star of the Sea is Florida’s second oldest Catholic parish, founded in 1846. Pope Benedict XVI raised the church to a minor basilica in 2012. You can enter the basilica and take a self-guided tour.

The Mel Fisher Maritime Museum contains an extensive collection of treasures and artifacts from 17th-century shipwrecks. The museum highlights the discoveries of treasure seeker Mel Fisher and his contributions to maritime archeology. Here, you can see Spanish gold coins, learn about the real pirates of the Caribbean, and explore the science of shipwrecks. Tickets are required. This is one of my top recommendations for families who want to learn more about the pirate history of Key West.

Key West Is Known As The Conch Republic  

Did you know  Key West  once seceded from the US and became its own country?  

In 1982, out of frustration over a border checkpoint that stopped most traffic into and out of the keys, Key West sarcastically notified the Federal government they were seceding from the Union. They gave their new country the name “Conch Republic.” 

This name has become a unifying moniker for the people of the Keys and a rallying cry for citizens who value freedom and independence. You’ll see the name all over. Even the Key West high school got the fever, naming their mascot the “Fighting Conch.”  

I laughed when I saw the Conch Republic’s official flag, which bears the motto “We Succeeded Where Others Failed.”

Key West Is Home To The Oldest Bar in Florida, or Is It?

Caption Tony’s is an iconic bar located just a block off Duval Street and was actually the original home of Sloppy Joe’s Bar. The sign out front says it’s the oldest bar in Florida. However, other sources say that the The Palace Saloon on Amelia Island is the oldest bar in Florida. I will have to pop in and ask them about it when I visit next month!

Did you know that Jimmy Buffett played Captain Tony’s in the early 1970s?

Key West Is A Fisherman’s Paradise

Anglers in the Keys have caught some of the largest fish on record in Florida. These include a 240-pound Yellowfin Tuna, a 243-pound Tarpon, a 612-pound Swordfish, and a 686-pound Great White Shark.  

Key West has a legendary reputation for fishing. Initially made famous by the stories of Hemingway, the coral reefs and deep blue waters of the Florida Straits are well-known for their massive catches.  

Fishing here is diverse, and many different fish are regularly biting. Tarpons are heavyweight champions and can top 200 pounds. Bonefish are called “Grey Ghosts”; they are smaller but harder to find. Snapper and Grouper can be caught year-round and are sought after for their great taste. They like patch reefs, wrecks, and bridges and can even be caught from shore. If you want to go farther from shore, Blackfin Tuna are wonderful to eat and very plentiful in the spring. Sailfish, Swordfish, and Marlin are the kings of the sea and will give you the fight of your life.  

These majestic giants drew Hemingway here and continue to thrill sport fishers with their strength and size. The warm waters off the coast bring in smaller Blacktip and Bonnethead sharks. Or you can pit yourself against apex predators like the giant Bull, Tiger, and Hammerhead sharks. 

Key West Was Once The Cigar Capital Of The US

Many people don’t know Key West was the original epicenter of the Cuban cigar industry in America.  

The first cigar factory started here in 1831, and by 1890, there were at least 80 factories in Key West. The factories were tightly connected to Cuba and would import Cuban tobacco leaves to be hand-rolled by Cuban emigres in Key West factories. The legendary Arturo Fuente began rolling here in 1912.  

After hurricanes hit Key West, destroying some factories, and local unrest around labor unionization, most factories moved to Ybor City in Tampa. Several small factories still operate in Key West, like the Key West Cigar Factory, Rodriguez Cigars, and the Island Cigar Factory. 

Jimmy Buffett Got His Start In Key West

The iconic singer and songwriter Jimmy Buffett moved to Key West in 1972. After having no success in the Nashville record business, he decided to take a trip with a friend to the Keys for some needed relaxation.  

He ended up living in Key West for seven years, working various odd jobs and singing in the local dives and honk-tonks. The island ambiance of the Keys inspired his casual style and tropical-themed lyrics. His hugely popular songs like Margaritaville became synonymous with Key West, and enjoying the salt and sea lifestyle became a popular pastime for fans worldwide.  

I read some amazing stories about Jimmy’s time in the 1970s in  Key West . He became part of a “Rat Pack” of close friends, many of whom were aspiring authors and poets, all following the spiritual footsteps of Hemingway. Stories of epic week-long deep sea fishing trips, hard-partying, and great friendship make this era of his life reminiscent of the “Lost Generation” of Paris ex-pats in the 1920s. 

A book I love that focuses on Jimmy and his rat pack in the 1970s is titled  Mile Marker Zero: The Moveable Feast of Key West .  And if you haven’t read  A Pirate Looks At Fifty , you must!

The Rum Runner Drink Was Invented Near Key West

Legend has it that the famous Rum Runner cocktail was invented in 1972 at the Holiday Tiki bar in Islamorada, near Key West.  

In one story, bartender John Ebert was challenged by the Holiday Tiki Bar owner to use up a lot of unused liquor that hadn’t been drunk (called “dead stock”). John mixed the ingredients in a new way to make the first Rum Runner.  

In another version of the story, John was looking for a job, and the owner of the Tiki Bar asked him as part of the interview to make a delicious drink with lesser-known ingredients.  

Either way, we now have the tasty Rum Runner – a sweet libation that has slaked the thirst of many a beach bum and tropical reveler around the globe.

Enjoy The History Of Key West On Your Next Trip

Key West history is filled with fascinating stories of larger-than-life personalities, rising and falling fortunes, boom and bust industries, and enduring people committed to life by the sea. Their stories are diverse, but they are all driven by fierce independence and a yearning for freedom away from society.  The fun thing about the history of  Key West  is that there are always new tales to listen to on every visit!

Key West is one of my favorite places to visit because of its charming eccentricity and its desire to be true to itself. It’s a fantastic place to relax, try new things, and enjoy the “Salt Life.” When planning your trip to the Conch Republic, be sure to set aside time to see some of the historical places. Catch the setting sun and sip a Rum Runner while you marvel at all this city offers.

And if you are looking for things to do in Key West, I have got you covered with several great Key West travel blog posts! 

• 18+ Things For Families to Do in Key West
• Riding the Iconic Conch Train Tour in Key West
• All About the 6-toed Hemingway House Cats
• My Momcation at the Marker Key West
• Visiting the Truman Little White House
• Snorkeling & Sunset Tours with Sebago Watersports
• The Key West Hop-On Hop-Off Old Town Trolley Tour

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The Sebago Difference

All jet ski tour groups with Sebago Watersports are kept intentionally small. With fewer total riders, our crew will guide you toward the routes that spark your interest

Sebago’s brand-new Yamaha jet skis are rated top of their class in safety and performance. With superior handling capabilities, unmatched speed, and reliable machinery, these vessels ensure a thrilling and safe high-speed escapade.

At Sebago Watersports, we offer several morning and afternoon departure times to fit your schedule and preferences. Just let us know the date and time you’re looking to book, and our dedicated crew will make it happen!

We’ve designed our jet ski tours to take place in ~90-minute intervals to give you ample time to explore the stunning waters of Key West. Keep your eyes peeled for wildlife and ask your guide to lead you to local landmarks and little-known gems that you may have never been able to see on land!

Whether you’re a newbie to jet skiing or were practically born on the water, Sebago Watersports’ guides will ensure that you feel 100% comfortable before setting out and throughout your journey!

Jet skiing not enough for you? Fear not! With Sebago Watersports, you can book a jet ski tour along with a variety of our other on-the-water activities, including parasailing, snorkeling, and a catamaran cruise – in fact, we recommend it.

Sebago Key West takes great pride in being Key West’s favorite watersports and tour company. It’s simple… Sebago offers the best tours at a great value. Our food is prepared fresh. Our crew is fantastic. And we never compromise on our ships or safety.

Sebago Watersports operations started in 1988 with the purchase of our first catamaran, the famous racing Sebago. For over 35 years, Sebago has provided visitors and locals with a true Key West sailing experience. Sebago is proud to be the longest established day-charter catamaran operation in the continental United States.

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CONTACT COURTNEY TO CUSTOMIZE YOUR VERY OWN WORRY-FREE DAY ON THE WATER.

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