Key West
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Viator
Boat Excursion in Florida Keys with Snorkeling Equipment
Trips are customizable - to a point. Your friendly, knowledgeable guide has experience with all sorts of ocean activities and knows the waters around the Lower Keys really well. So there are a few different areas to choose from on where to go and we can decide based on weather, wind, etc. There is the option to bring up to 2 kayaks ($25 rental fee per kayak). Snorkel equipment available (just let us know in advance sizes). The guide would be glad to hop in and point things out just let him know ahead of time. Possibility of seeing dolphins. We love the ocean and have a passion for being on or under the water! Also we are kid friendly!
5.0(22)
4 Hours
Key West
- Free cancellation
- Private tour
From
$700
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Viator
Private Looe Key Snorkel from Big Pine Key
Looe Key Marine Sanctuary is part of the Great Florida Reef, the only coral reef in the continental USA, and the third largest barrier reef system after the Great Barrier Reef in Australia, and the Palancar Reef in Mexico and Belize. It is a special place for snorkeling.
5.0(442)
3 Hours
Key West
- Free cancellation
- Private tour
From
$599
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Viator
Shark and Wildlife Viewing Adventure in Key West
This is the only shark tour in the USA and to our knowledge the only tour where guests do not get in the water to view the sharks. Delight in close-up views of sharks and a variety of other marine life. In this eco-friendly catamaran, travel through shallow waters to a location a few miles from shore, observing dolphins, stingrays, barracudas and native birds along the way. Bait is used to attract lemon, nurse and other types of sharks to the side of the boat. Learn all about Key West wildlife and enjoy complimentary soda, juice and chips throughout this family-friendly tour.
5.0(3245)
2 Hours
Key West
- Free cancellation
- Likely to sell out
From
$99
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Viator
Guided Bike Tour of Old Town Key West
Ride with Key Lime Bike Tours for a truly unique and unforgettable Key West experience! See the islands top attractions with your own friendly knowledgable guide! Cruise Old Town, visit iconic landmarks, and hear stories about some of the colorful characters that have called Key West home. You will get the best Key West photos and see more in two hours then most visitors see their entire trip to Key West. Ride a bike from the Gulf to the Atlantic and see the Southernmost from Coast to Coast! Voted Key Wests #1 Land Excursion 10 years in a row! ALL OF OUR AMAZING RIDERS ALSO RECEIVE DISCOUNTS ON BIKE RENTALS AND OUR AWESOME MERCH! Cold bottled water and Key Lime pie included!
4.9(2705)
2 Hours
Key West
- Free cancellation
From
$59
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Viator
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
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
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
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
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
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 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
Sunset Sail in Key West with Beverages Included
Key West is famous for fabulous sunsets and Floridays is famous for our spectacular uncrowded champagne sunset cruise. Our reputation for personal service and attention to detail on our sunset cruise is legendary. Being out on the water for a Key West sunset is like being IN the sunset itself. There is nothing quite like it. Who knows, you may get lucky enough to witness that elusive green flash!
4.9(954)
1h 30m
Key West
- Free cancellation
From
$79
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Viator
Florida Keys Nature & History Tour from Key West
With your friendly and knowledgeable tour guide, this 4 Hour VIP Tour of the South Keys promises to amaze you. En route, you’ll learn the history, culture, and ecology of the Keys, listen to island music, and enjoy the breathtaking scenery! Feel free to ask questions, share your experiences, and point out wildlife. * We drive you from island-to-island on the iconic Overseas Highway, about 45 miles from Key West & over 20 bridges * Revel in the scenery as we drive over the iconic 7-Mile Bridge - twice! * Experience world-famous Bahia Honda State Park: dip your toes in the Gulf of Mexico AND the Atlantic Ocean, walk on a historic railroad bridge for spectacular views, and more! * Photograph endangered Key Deer on Big Pine Key on our world-famous Key Deer Safari * Visit the Blue Hole to check for alligators and other native wildlife You'll love this tour so much, you'll book it again next year! We sanitize our tour vehicles before each tour in accordance with CDC recommendations.
4.9(115)
4 Hours
Key West
- Free cancellation
From
$119
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Viator
Key West Cocktail Cruise Adults Only Sunset Cruise with Open Bar
“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!
4.8(177)
2 Hours
Key West
From
$65
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Viator
Key West Deep Sea Fishing: Big Fish
If you’re looking for some of the best fishing that money can buy out of Key West, Florida, you can’t go wrong with Corsair 2 Sportfishing. With over 3 decades of local fishing experience under his belt, Captain Russ McKinley is your man if you want to get the best out of these deep blue waters. His boat is a 50’ Hatteras saltwater fishing boat that can take up to 6 anglers fishing at the same time. Powered by twin 550 HP Detroit Diesel engines, this fishing machine is unstoppable on the water. The vessel comes rigged with state-of-the-art navigational electronics and safety equipment, outriggers, a fighting chair, a live bait tank, and ice-boxes. It’s also very comfortable and features 2 private restrooms, a kitchen, a flybridge, beds, and AC. This beauty can take you for some amazing deep sea and reef fishing up to 18 miles offshore on full day trips. This trip will also provide higher chances of catching Marlin!
4.8(113)
4 Hours
Key West
- Private tour
From
$1,000
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Viator
Key West Kayak Rental
A 2 hour kayak rental will allow you to explore the calm, clear waters between Stock Island and Key West on your own from the comfort of your single or double kayak (book per person not per kayak) Glide over sea grass and through mangrove tunnels as you look for fish, birds, sharks, rays and maybe even a manatee. Great for paddlers of all experience levels though all guests must know how to swim.
4.8(127)
2 Hours
Key West
- Free cancellation
From
$40
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Viator
Marathon: Historic 7-Mile Bridge Sunset Cruise
✔️ What Sets This Sunset Cruise Apart - Friendly, attentive local crew focused on guest experience - Spacious, comfortable boat with excellent sunset views - Calm, relaxed atmosphere (not a party cruise) - Light island music that never overpowers the moment - Crew happy to help take photos during golden hour
4.8(57)
1h 30m
Key West
- Free cancellation
From
$125
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Viator
Key West Parasailing - Next to Cruise Port with Amazing Views
Fury’s Key West Parasailing offers an exhilarating way to experience the stunning beauty of Key West from the sky. This unique adventure combines breathtaking views with the thrill of flight, making it a must-do for both beginners and seasoned adventurers. As you take off, you'll feel the rush of soaring above the azure waters, enjoying bird’s-eye views of the island that are truly unmatched. You can fly tandem or triple, depending on the Captain's discretion, ensuring a safe and fun experience for everyone. One of the standout features is the optional ocean dip, where you can cool off in the refreshing waters before heading back up into the sky. Keep an eye out for dolphins swimming below or colorful tropical birds alongside you for added excitement. To capture these unforgettable moments, digital photos are available for purchase at the end of your trip. Get ready for a sky-high adventure that combines thrill, beauty, and lasting memories!
4.8(421)
50 Minutes
Key West
- Free cancellation
From
$64
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Viator
Key West Historic Old Town Food Tour with 5 Authentic Tastings
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.
4.8(306)
2h 30m
Key West
- Free cancellation
From
$108
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