Tours in Key West

This isn’t a packed tourist boat — it’s a true small-group adventure with a maximum of 6 guests. You’re not watching dolphins from far away; you’re close enough to feel that electric moment when they swim right next to the boat. Our captains know the dolphin pods by territory and behavior, so you spend more time with them and less time searching. After the dolphin encounter, we take you to hand-picked spots that big boats can’t access: clear, shallow water, quiet backcountry reefs, and hidden sandbars. Beginners feel safe, families feel relaxed, and experienced snorkelers get genuinely good underwater visibility. Personalized, unhurried, and run by a local crew that actually cares — that’s what sets this trip apart.

Join us on a sip and stroll through Key West's craftiest bars and hidden local gems enjoying 5 local cocktails & 2 food tastings! Discover the iconic stories behind Key West’s signature drinks, like the Hemingway Daiquiri, and explore the sights, sounds, and “intoxicating” flavors of the tiki era, each of it’s 5 stops revealing a new secret. Travel off Duval Street and into neighborhood bars that locals frequent! Sample delectable bites and nibbles between drinks to get a taste of what the island life is all about. Curated with fun-lovers in mind, this upscale bar crawl is ideal for those who are more inclined to mingling and exploring Key West’s vibrant bar scene. Tastings include asian cauliflower bites, taco of your choice, 4 delicious hand crafted cocktails, locally-made beer, and much more. Our group size is limited to 12 people to ensure personal service from the guide.

You will begin this 1 hour and 30 minute guided tour by meeting your tour guide, (who will be wearing a neon green shirt) at Margaritaville. Musician Jimmy Buffett arrived in Key West 50 years ago in 1971. This walking tour will take you to the locations around Old Key West that inspired his songs, where he played his first gig, some of his favorite watering holes, places he ate, bars he played in, and his recording studio. You will get to eat a slice of the best Key Lime Pie, before visiting the location of the first Margaritaville, Mallory Square, and end at Capt. Tony's Saloon. Included is a souvenir alcoholic beverage.

Discover the flavors of the ocean on this locally guided 3-hour food tour of Key West. Savor maritime history through delicious seafood (or tasty non-seafood options) cuban sandwich & key lime pie tastings. Sample classic ingredients like Key West pink shrimp, Caribbean warm-water lobster, and fresh fish. Sip white wine after walking through the tropical neighborhood streets. This small-group tour is limited to 12 people, and you'll leave with a greater understanding of the industries that shaped our island and culture. Joining a fish lover, but not one yourself? No problem, we’ve got you covered with equally delicious substitutions.

Join us for a snorkel adventure to the only living coral reef in North America. We have several fantastic reefs to choose from on both the north and south sides of Key West, each offering a unique experience. It’s about an hour trip out to the reef, we will have you there for an hour and then a one hour journey back to our dock. We will provide instruction on how to use the equipment but recommend that you are comfortable in water over your head and that you have the ability to swim. *We provide quality sanitized mask, snorkel, fins and flotation vest *Professional guidance and instruction on how to use provided gear *Fresh water hose available to rinse off after snorkeling *Complimentary beverages to include water, soda, white wine, a selection of craft beers, margaritas, and champagne *Floridays takes a limited number of guests so that we may provide you with the ultimate in enjoyment and service

Dip and Sip Key West Snorkel Trip on The 65 foot custom built Sandie Cat. Your 3 hour snorkel trip will start a sail to the Key West living reef where you will see coral and tropical fish. All snorkeling equipment is provided and if you need help our professional crew will give you instruction on how to snorkel. After your snorkel we have fresh water showers so you can rise off. You will enjoy a sail back to the dock and enjoy Free Beer, soft Drinks and water as you enjoy your ride on our big open decks.

The Hemingway Experience celebrates Key West’s most infamous author, Ernest “Papa” Hemingway, with a historical walking adventure retracing his steps on a "Bucket List" tour of Old Town. Our 4-hour guided experience stops at (6) locations, helping tell Hemingway’s story in Key West & Cuba. Each ticket includes guided entrance into his famed Key West home. Then eat, drink, and explore the island on foot through “Papa’s eyes”, feasting on Cuban cuisine (& 3 boozy beverages) while your knowledgeable local guide impresses with interesting stories & amazing fun facts. The adventure takes you behind the scenes of a 3rd generation family run cigar rolling factory, and into the newly remodeled Social Club at Hemingway Rum Co. for his favorite drink made with his family company’s premium rum. Then finish with a slice of our famous key lime pie! After the tour, you’ll receive a collection of exclusive recipes, recommendations on restaurants, attractions, entertainment, and cultural offerings.

Gulfstream Fishing is the longest-running party boat fishing charter in Key West, catching steady loads of reef fish since 1947. Our 58-foot Gulfstream IV carries up to 45 passengers and is inspected twice a year by the U.S. Coast Guard. Powered by twin Detroit 8v92 turbo engines, she gets you to the fishing grounds quickly and safely. Once we anchor, you’ll have everything you need on board—men’s and women’s restrooms, shaded seating, and a small galley with snacks and drinks. Our captains and mates help everyone from first-timers to experienced anglers. They’ll bait your hook, untangle your line, and keep you fishing. You’re welcome to keep or release your catch. Fish cleaning is available for a small per-fish fee, or you can take them whole. Coolers are allowed, and you’re free to bring your own food and drinks. If you want a fun, affordable, classic Key West fishing trip for all ages, this is it.

Embark on an adventure off the shores of Key West, where the turquiose waters of the Gulf of Mexico and the Atlantic Ocean meet in a symphony of beauty and tranquility. Your day begins as you board a luxurious catamaran, your vessel for a day of exploration and relaxation. Sailing away from the bustling Key West harbor, feel the gentle breeze on your skin and the warmth of the tropical sun overhead. As the catamaran glides smoothly over the crystal-clear waters, you'll have the opportunity to soak in panoramic views of Key West's picturesque coastline, dotted with palm-fringed beaches and vibrant coral reefs. Keep your eyes peeled for playful dolphins frolicking in the waves or graceful seabirds soaring overhead. After a leisurely sail, stop at a secluded snorkeling spot, where the underwater world awaits exploration. After working up an appetite, indulge in a delicious gourmet breakfast and unlimited mimosas, all while enjoying stunning views and the company of fellow travelers.

*Visit Stockislandboatcharters.com for alternate availabilities and pricing.* Embark on a tour through the beautiful Florida Keys mangrove back country. Stop at various sandbars to paddle board, snorkel, or just hang out. Watch for wildlife throughout the trip such as dolphins, sea turtles, fish, birds, and much more! A cooler filled with ice and bottled water will be provided. Feel free to bring any food or alcoholic beverages.

Billy started his Island Jet Ski Tour in 1992. There are many imitators, but only one Original Island Jet Ski tour! Our guides are licensed and local, so they know the waters surrounding our island like their backyard - because it is! Our tour route changes dependant on the weather & waves of the day - we modify our tour to be comfortable and give you the longest Freeplay time possible, so you can drive it like you stole it!

I founded and own HONEST ECO. With Kentucky bluegrass roots and a B.S. in Biology, I found a world with a blue sea too alluring to ignore. I arrived to Key West in 2005. Now I have 10+ years of experience studying Biology and being on the water in Key West. I now own a small business with my wife and 2 young kids. We are trying to make a big impact by educating and leading by example. I'm very passionate about being respectful to the wildlife and the environment

Historic Schooner. Champagne Sunset Toast. Elegant and Exclusive. Step aboard the historic schooner When And If, commissioned by General George Patton in the late 1930s, and sail into a breathtaking Key West sunset. Raise a champagne glass as the sun dips below the horizon, while your experienced crew handles the sails — or try your hand at steering this classic wooden schooner yourself. Glide along turquoise waters, spot playful dolphins and local wildlife, and enjoy an unforgettable evening that blends history, luxury, and adventure. Highlights: Historic schooner experience aboard the When And If, commissioned by General George Patton in 1939. Champagne sunset toast included Elegant and exclusive cruise - Avoid the crowds Hands-on sailing opportunity: take the wheel under guidance from your experienced crew. Spot dolphins, sea birds, and local marine wildlife. Perfect for romantic evenings, family adventures, or history enthusiasts — children sail at a discounted fare.

Make the most of your Key West vacation by exploring the island with Fury’s golf cart rentals. Forget the long walks and drive straight into the adventure! Cruise through the Conch Republic like a local with our gas-powered golf cart rentals. Feel the refreshing sea breeze as you effortlessly navigate Key West’s charming streets in our high-quality street-legal golf cart rentals. Experience the thrill of driving down Duval Street with friends or family in our comfortable four- to six-passenger golf carts. Our top priority is your safety and enjoyment, so each golf cart rental is carefully maintained to ensure a smooth ride. Experience Key West in a fun, convenient and unforgettable way with Fury’s golf cart rentals!

Go Beyond Snorkeling is the closest you can get to scuba diving without being Dive Certified! Go Beyond Snorkeling into new depths for greater durations where you can easily and safely breathe underwater without heavy, cumbersome dive gear. Discover amazing coral formations, schools of tropical fish, and swim alongside colorful creatures as you glide effortlessly beneath the waves.

Experience Key West like never before on Fury’s 90-Minute Jet Ski Tour! Perfect for adrenaline junkies, this thrilling 28-mile adventure takes you around the island’s stunning coastline, and scenic backcountry. Ride solo or with friends and enjoy the speed and beauty this tour has to offer. You'll hop aboard our brand-new Sea-Doo Jet Skis- the most advanced in Key West, known for their unmatched performance and smooth ride. Guided by our expert team, you may cruise past iconic sights such as Mallory Square, the Southernmost Point or Ft. Zachary Taylor with the wind in your hair, you may even spot wildlife like bottlenose dolphins and sea turtles. The tour includes several stops at points of interest, often including a sandbar, and a chance to cool off in the water while soaking in the breathtaking views. Whether you're a seasoned rider or a first-timer, this action-packed tour promises an unforgettable Key West experience filled with fun, adventure, and natural beauty!

Key West is famous for it's sunsets and it doesn't get any better then on an intimate sunset cruise aboard our custom tiki bar boats. You and up to 5 guests will toast the sunset with your favorite libation(BYOB). Tours depart an hour and fifteen minutes prior to sunset so we can get to the perfect place to watch the sunset. Our boats feature a large thatch roof for shade, bluetooth stereo, a walk in bathroom, adjustable padded bar stools and a gorgeous live edge tiki bar. You'll cruise the Key West harbor in style and view the famous sunset on your private 2 hour adventure. Keep your eyes on the horizon for a chance to see the famous Green Flash as the sun goes down.

Avoid the crowds and Sail on Key West’s beautiful shallow waters on this Adults Only Sunset & Moët cruise, to sip Moët & Chandon champagne and indulge your palate while being washed in the colors of the Key West sunset! Included in the tour price is bottomless house champagne Chandon Brut, 8 premium red and white still wines, ice-cold beers & White Claws, and a champagne-inspired Gourmet Cheese Buffet (naturally gluten free) that includes 4 incredible international cheeses, paired plump berry tray, local smoked fish dip, crunchy crisps and fresh-baked crusty bread. Two other Moët & Chandon champagnes are available for additional purchase - both at wholesale price - only for onboard guests. Key West is famous for its tropical sunset, and there’s no better way to watch it than on this famous Sunset & Moët Cruise. This public trip is always limited to 14 adult passengers on a 28 person sailing catamaran, for guests comfort and quality control. And NO kids!

Enjoy this 3 hour sunset combo trip. We will cruise out to Key West’s best reef location, where you are welcome to jump in and enjoy an evening snorkel. If you do not feel like getting in the water, no worries, the bar is open! Grab a draft beer or glass of wine & enjoy the views. Once done snorkeling we will venture out on a one of a kind sunset cruise.

Discover the flavors of paradise on our Key West food tour through the colorful streets of Old Town. Guided by locals, you’ll enjoy 5+ tastings that celebrate the island’s unique mix of Cuban, Caribbean, and Floridian influences. Start with a refreshing iced coffee before biting into golden, crispy conch fritters—a true island classic. Savor authentic Cuban cuisine that reflects Key West’s cultural heritage, then indulge in rich chocolate-covered Key lime pie, the city’s most famous dessert. Along the way, your guide will share stories of pirates, poets, and island life, bringing the history and charm of Key West to life. To end, you’ll taste our exclusive Secret Dish, a surprise that makes the experience truly unforgettable. This is Key West beyond the postcard—an authentic taste of its food, culture, and soul.

“The Key West Cocktail Cruise is the best thing to happen to Sunsets since cameras and sunglasses!” This is not your average Key West pleasure cruise.   Our 2 hour Key West Cocktail Cruise is what happens when true Hospitality Professionals take you out for an evening on the water!  You’ll never find Sierra Mist in our Margaritas — just natural ingredients, hand-crafted to perfection and served with precision. "All Inclusive" Craft Beer, Fine Wine and of course Craft Cocktails are featured each night onboard our spacious 47’ catamaran.  We offer a full range of House Specialty Cocktails, California Wines, and South Florida Craft Beer. Our intention is to amaze our guests with 5-star service, and to offer a fresh and unique Sunset Experience every single evening!

Tour the historic Harry S. Truman Little White House in Key West and learn about a fascinating period of American history. What was once a private compound on a U.S. Navy base is today open to the public as a museum. Listen to fascinating stories told by informative guides about the history of the house, which was built at the beginning of the 20th century. Learn what Thomas Edison and Dwight D. Eisenhower did during their stays, and, of course, about Harry Truman’s long love affair with this gem of a property.

Discover the charm of Marathon, FL, with a delightful Sandbar Experience and Sightseeing Cruise. Enjoy a 4-hour adventure exploring the local scenery on a comfortable boat, complete with unique views of the island. Spend a relaxing day at the sandbar, where you can swim in the crystal-clear waters, or opt for kayaking and paddleboarding to enhance your aquatic adventure. Light snacks, drinks, and friendly crew members ensure a fun-filled day for all ages. - 4-hour tour ideal for families and all ages - Scenic boat ride to the sandbar with opportunities for swimming and water sports - Light snacks and drinks provided; guests can bring their own food (no glass or hard alcohol) - Relaxed atmosphere with ample time to enjoy the beautiful waters and surroundings

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