Key West
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Key West USCGC INGHAM Maritime Museum
The USCGC INGHAM was the longest continually serving, most decorated ship in Coast Guard History. Serving in active duty from 1936 to 1988. Only remaining American ship afloat to have fought in the Battle of the Atlantic. Command ship for several Philippines landings including General Douglas MacArthur's return to Corrigedor, he was aboard during this action. First allied vessel into Chinese waters at wars end. Two Presidential Unit Citations for support missions in Viet Nam. Also part of the Mariel Boatlift, when tens of thousands of Cuban refugees left their island home seeking refuge in the U.S. Now a National Historic Landmark and Coast Guard National Memorial to Guardsmen that have lost their lives in World War Two and Viet Nam. The Ingham also offers one of the best sunset views in Key West.
4.9(81)
20 Minutes - 2 Hours
Key West
- Free cancellation
From
$23
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Key West Small-Group Sunset Sail with Wine and Hors d'oeuvres
The Wind & Wine Sunset Sail offers a boutique experience unlike any other in Key West! This isn’t your typical party boat—it’s a calm, uncrowded sail aboard a historic schooner with an intimate, relaxed vibe. You’ll enjoy a guided tasting of fine wines from around the world, along with a selection of craft and domestic beers and light hors d'oeuvres including crudites, meats, cheeses, crackers, fruit, and chocolate. With small group sizes, there’s plenty of space to move around and enjoy the view without the crowds. It’s perfect for a romantic date or a fun evening with friends—upscale, but never uptight. What really sets this trip apart is the crew. They’re fun, welcoming, and passionate about what they do—ready to pour your next glass, share a story, or make sure you’re having a great time. Add in a Key West sunset, and you’ve got one of the most unique and enjoyable evenings on the water!
4.9(1441)
2 Hours
Key West
- Free cancellation
- Likely to sell out
From
$135
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Viator
Personalized Key West JetSki Tour for Small Groups Nearly Private
Almost Private Jet Ski Tour – Voted Key West’s Best Get ready for the most exclusive jet ski experience in Key West. With only 2 to 3 jet skis per outing, this tour offers the closest thing to a private adventure on the water. It's the perfect way to explore the island without the crowds — just you, your guide, and the open ocean. Voted Key West’s Best Jet Ski Tour and backed by over 15,000 five-star reviews, this small-group tour circles the entire island on a 28-mile guided ride. You'll stop at iconic landmarks like the Southernmost Point, a hidden local sandbar, and scenic spots throughout the Florida Keys Nature Sanctuary. Drivers and riders can switch at the stops, so everyone gets a turn behind the handlebars. There are no hidden fees — everything is included. You’ll enjoy a free second rider, complimentary shuttle pickup (based on availability), and all fuel and safety equipment provided at no extra charge.
4.9(51)
1h 30m
Key West
- Free cancellation
From
$169
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Viator
Private Key West Sandbar and Paddle by Boat
Enjoy a private half day adventure for up to 6 guests aboard our late model pontoon boat. Guests may discover and observe diverse marine habitats and wildlife refuges as well as spot an abundance of marine birds and sea life. Paddle on your own via kayak or paddleboard through natural, winding, mangrove lined tidal creeks and then relax on a sandbar or island on one of our floats. Bring your own snacks and drinks and your dog!
4.9(37)
3h 30m
Key West
- Free cancellation
- Private tour
From
$600
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Viator
Classic Key West Schooner Sunset Sail with Full Open Bar
There's no better way to savor the magic of a Key West sunset than aboard a majestic schooner, complete with a full open bar. This enchanting journey blends the timeless elegance of traditional sailing with the lively spirit of Key West, promising an unforgettable experience for all. As you sail further into the sunset, the full open bar comes to life, offering an enticing array of cocktails, wines, and spirits to complement the evening's splendor. Sip on our signature Schooner Bloody Mary or Dark & Stormy as you watch the sky ignite with color. The skilled bartenders are on hand to craft your favorite drinks, ensuring that your glass is never empty as you drink in the sights and sounds of the sea. As the schooner begins its journey back to Key West, you find yourself lost in the timeless rhythm of the sea, grateful for the opportunity to witness the beauty of a Key West sunset from the deck of a historic schooner.
4.9(240)
2 Hours
Key West
- Free cancellation
- Likely to sell out
From
$109
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Viator
Full-Day Tour of Florida Keys Including Aquarium Encounters from Key West
Depart the island of Key West & enjoy a full day of sightseeing along the iconic Overseas Highway! You'll travel halfway up the keys to Marathon and stop along the way to explore the natural splendor and man-made wonders of the Florida Keys. Such stops will include the Florida Keys Aquarium Encounters, Bahia Honda State Park, and the Blue Hole on the National Key Deer Refuge. Your driver will provide fun and interesting commentary along the way. This tour will have a maximum group size of 12, with filtered water, lunch, and entry fees included. Customizable for private tours, call to make your tour private!
4.9(36)
7 Hours
Key West
- Free cancellation
From
$169
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Viator
Dinghy Drinking Tour through Key West Waters
On this tour, you will see the beautiful crystal clear waters around Key West from a dinghy, a small motor boat that seats up to 5. An experienced licensed boat captain who knows the waters will lead your tour. Dinghies can go through narrow tunnels in the mangrove trees that bigger boats cannot get through. Be ready to duck under branches. We will stop at waterfront bars. 2 or 3 stops depending on your preferences. If your group is larger, we will arrange additional boats. You can get in the water to swim or wade at any time. You will see lots of fish and sea creatures. Most of our guests bring beer, water or other beverages along for the tour. We have coolers to keep them chilled.
4.9(107)
3 Hours
Key West
- Free cancellation
From
$85
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Viator
Key West Craft Cocktail Crawl
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.
4.9(569)
3 Hours
Key West
- Free cancellation
- Likely to sell out
From
$94
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Viator
KeyWest Half-Day Inshore Fishing Private Charter
These trips are very customizable trips from all skill levels of charter fishing to just kicking it at the sandbar we are here to make this the best part of your vacation.
4.9(68)
4 Hours
Key West
- Free cancellation
- Private tour
From
$750
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Viator
Schooner Appledore Day Sail with Full Bar in Key West
Experience sailing Key West on a majestic 2-masted schooner, just like adventurers from the 19th century, while enjoying the luxurious state-of-the-art accommodations of a modern passenger schooner. Her decks are spacious and comfortable. Feel the sense of adventure as the crew hoists the sails. Participate in this age-old tradition by helping raise the sails. Take a turn at the wheel and feel the exhilaration of captaining a traditional tall ship.
4.9(113)
2 Hours
Key West
- Free cancellation
From
$49
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Viator
Key West Day Sail on Schooner America 2.0 with 2 Drinks
Sail aboard the fastest and most elegant schooner in Key West, Schooner America 2.0! This boat is a replica of the 1851 Schooner America that won the first America's Cup Race in 1851. Admire her beauty on the clear, calm Caribbean waters while sipping a beverage. Take in views of Key West sights like Fort Zachary Taylor, Mallory Square, Sunset Pier and Sand Key Light Tower. Soda and water are complimentary. Two alcoholic beverages are included with your ticket. Additional beverages are available for purchase.
4.9(212)
1h 30m
Key West
- Free cancellation
- Likely to sell out
From
$79
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Viator
PRIVATE Welcome to Key West Walking Tour
Welcome to Key West! Stroll through Old Town Key West with a long-time local, see & learn about the unique places you can visit during your vacation. This is private tour is customizable, meaning you can request to adjust the meeting point to better suit your day, and even request what kind of stories you'd like to hear. Perfect for wedding party, couples, family & friends, bachelor/bachelorette, birthdays, reunion, corporate groups, and more! If it's too far or too hot to walk, you can hop on the Duval Loop bus with your guide It's air-conditioned with several convenient stops throughout Old Town. The best part about your own private tour is you can ask questions and customize the tour to your interests! Feel free to include notes in your booking about: - what you want to know about Key West - points of interest you'd like to include - if you're celebrating an event - mobility challenges or other needs we can accommodate Total distance about 1 1/2 miles.
4.9(22)
1h 30m - 3 Hours
Key West
- Free cancellation
- Private tour
- Likely to sell out
From
$138
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Viator
Key West Mangrove Kayak Eco Tour
Along with your experienced guide you will paddle at a relaxing pace and explore the shallow, calm, blue-green waters of the back country of Key West. You will glide through the winding mangrove creeks and paddle through inches of water, where you can easily view and learn about the geological structure of the Keys along with its inhabitants, all from the comfort of your kayak. Your adventure will give you a chance to view the mangrove environment up close, along with its marine life including tropical fish, crabs, sea stars, jellyfish, sea cucumbers, sponges and various aquatic birds. Every trip leads us on a different adventure! all guests must know how to swim. Rest rooms to change on site. No lockers but things can be left behind at paddle shack. Beginners welcome!
4.9(2341)
2 Hours
Key West
- Free cancellation
From
$80
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Viator
Half-Day Trip from Key West with Kayaking, Snorkeling & Sunset
This trip combines sailing, snorkeling, kayaking, and local insight in a laid-back, small-group setting. You'll sail on an authentic schooner into the calm, protected waters of the Key West National Wildlife Refuge—a remote area only accessible by boat. With group sizes limited to 20 guests, the experience feels personal, spacious, and relaxed! Our crew truly sets us apart. They’re knowledgeable, passionate, and always ready to share the history, wildlife, and ecology of the Keys in a fun, engaging way. Whether you're in the water or relaxing on deck, they’re there to guide, support, and make everyone feel welcome—regardless of experience level. Snacks, beer, wine, soda, and water are included onboard, adding to the comfort of your time at sea. If you join the afternoon trip, you'll also enjoy a beautiful sail back to Key West timed with the sunset, making the day even more memorable.
4.9(1759)
4h 30m
Key West
- Free cancellation
- Likely to sell out
From
$125
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Viator
Biologist Owned & Operated: Dolphin Watching & Guided Snorkeling
Introducing Squid! The quietest experience you will have on a boat while watching dolphins. We worked with David Walworth, an MIT educated Naval Architect and Principal Engineer known for his high-efficiency catamaran designs, to build the perfect boat for our trips from scratch. Our amazing crew are closely trained by our Honest Eco Biologists. Crew training starts on land with research and mission alignment before moving onto the water where we hone our seamanship skills and work to become as effective as possible at delivering on our Purpose. We Work to Spread the Value of Wildlife Conservation “People Protect What They Love.” Jacques Costeau said it, and it inspires us at Honest Eco as we work to help people discover and fall in love with the environment we are all part of. We are continuously learning and pushing ourselves to be as environmentally responsible as possible.
4.9(555)
4 Hours
Key West
- Free cancellation
From
$143
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Viator
Key West Schooner Sunset Sail with Bar & Hors d'oeuvres
Enjoy an exquisite 2-hour sunset sailing adventure aboard a stunning modern-built schooner! Take in the sights aboard Schooner America 2.0, the most elegant schooner in Key West, as you sail by Mallory Square, Sunset Pier, Sand Key Light Tower and more. Enjoy complimentary beverages throughout your sail along with individually plated hors d'oeuvres. Sit back and relax as your captain sails you effortlessly through the emerald green Key West waters and off toward the horizon for a quintessential Florida sunset experience.
4.9(893)
2 Hours
Key West
- Free cancellation
- Likely to sell out
From
$123
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Viator
Key West Full-Day Ocean Adventure: Kayak, Snorkel, Sail
Danger Charters is the only tour operator in Key West offering sailing excursions on a historic schooner into the remote backcountry of the National Wildlife Refuge. Our trips are truly small-group, with a max of around 20 guests, so you'll never feel crowded—whether you're snorkeling, kayaking, or relaxing on deck. On the Premium Day Trip, we often stop at a shallow sandbar, a guest favorite for swimming, wading, or just enjoying the view! What really sets us apart is our crew. They're passionate about what they do, and it shows in the way they lead each activity, share local history, and give fun, informative eco talks. Whether you're brand new to snorkeling or a seasoned paddler, the crew offers guidance, support, and an easygoing atmosphere that makes everyone feel welcome. This trip combines adventure, education, and laid-back sailing in one of the most beautiful and untouched parts of the Florida Keys.
4.9(813)
6h 30m
Key West
- Free cancellation
- Likely to sell out
From
$159
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Viator
Private 90-Minute Harbor Sailing Charter in Key West
Live the high life on this private chartered day sail in Key West. Set sail on your boat for a 90-minute adventure around the Florida Keys and view the city from the water in peace and tranquility. You may even get to see some friendly dolphins off the bow!
4.9(19)
1h 30m
Key West
- Free cancellation
- Private tour
From
$395
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Viator
Southernmost Food & Cultural Walking Tour by Key West Food Tours
Enjoy a taste of Key West on this 3-hour food walking tour, led by an expert guide. Along the way visit 5 locally-run “mom and pop” establishments in historic old town, dining on typical Cuban dishes, local seafood, and of course -- Key Lime Pie. Food samples are enough for a hearty lunch. Between tastings walk like a local, away from the touristy streets, as your guide shares insights about city history, food and architecture. This is a small-group tour, with a maximum of 12 people, ensuring a personalized experience.
4.9(1874)
3 Hours
Key West
- Free cancellation
- Likely to sell out
From
$90
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Viator
Small Group Key West Adult Sunset & Moët Sail & Amazing Cheeses
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!
4.9(987)
2 Hours
Key West
- Likely to sell out
From
$109
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Viator
Key West Schooner Backcountry Eco Tour Sail Snorkel and Kayak
Departing from Key West’s Historic Seaport, the Appledore Star’s sails are raised for an authentic sail experience on the way to Key West’s backcountry. Your day is spent exploring Key West’s uninhabited mangrove islands in the Key West National Wildlife Refuge. Keep an eye out for dolphins, sea turtles, manta rays and many other wildlife that call the Refuge home. Your captain knows where dolphins are frequently seen and will let you know if he spots any. Upon reaching the mangrove islands, the schooner anchors and your exploration begins. Your day is divided between guided kayaking tours and guided snorkeling tours. The warm, shallow water is calm, sheltered by the uninhabited mangroves, making kayaking a breeze. After your tours, come back aboard and wash off with our fresh water rinse, and relax on deck. Choose from plenty of complimentary cold drinks – frosty cold beer, wine, homemade sangria, chilled sodas and filtered water. This is the best of laid-back island living.
4.9(102)
5 Hours
Key West
- Free cancellation
From
$119
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Viator
Guided Mangrove Eco Tours Kayak or Paddleboard Adventure
Explore the serene mangrove waterways of Geiger Key on this guided eco-tour. Perfect for all ages and levels of experience. Choose between a single kayak, double kayak, or stand-up paddleboard as you glide through the lush scenery. Your knowledgeable guide will point out the hidden gems of this unique Florida Keys ecosystem, ensuring a memorable and educational experience. With safety gear, paddle instruction, bottled water, and dry bags provided, all you need to bring is your sense of adventure. Enjoy complimentary shuttle pick-up from Key West and immerse yourself in nature for two hours of tranquility.
4.9(18)
2 Hours
Key West
- Free cancellation
From
$75
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Viator
Key West Historic Seaport Food & Walking Tour
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.
4.9(671)
3 Hours
Key West
- Free cancellation
- Likely to sell out
From
$93
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Viator
Key West Photo Shoot at Your Resort or Beach
Whether you are visiting Key West for a special occasion, Anniversary, Romantic Getaway, Family Reunion. We can meet you at your Resort or one of Key West beaches to have a personal photo shoot We are at times available for Sunset timeframe and on weekends, so please email me for availability directly - This is priced for (1) couple or (1) family unit - not group extended family - please ask for pricing for larger groups.
4.9(35)
45 Minutes
Key West
- Free cancellation
- Private tour
From
$350
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