Key West
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Viator
Private Boat Tour to Sand Bar Snorkel Dolphins and Sunset
Join me, a true seventh-generation local captain for a personalized Key West adventure on my private boat. Spend the day exploring the stunning turquoise waters and hidden islands of the Florida Keys, with opportunities to snorkel, search for dolphins, visit a sandbar, enjoy light fishing, or simply relax and take in one of Key West’s world-famous sunsets. Every trip is fully private and tailored to what you want to experience — whether it’s adventure, leisure, or a bit of both. Departing conveniently from Garrison Bight Marina, your journey promises incredible views, local insight, and unforgettable memories on the water.
5.0(27)
3h 30m
Key West
- Free cancellation
- Private tour
From
$600
No similar experiences found
Viator
Key West Historic Private 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. As a private tour, everything works around you! Our start times are much more easy going, dates can open up. It's a much more intimate and cozy experience.
5.0(15)
2h 30m
Key West
- Free cancellation
- Private tour
From
$370
No similar experiences found
Viator
Hula Hank's Key West Tipsy Tiki Sunset Cruise
Imagine gliding over gentle waves aboard the Lazy Lady, a 53-foot, one of a kind tiki boat. Soak in the vibrant colors of an iconic Key West sunset - hues of orange, pink and purple. Sip on ice-cold beverages prepared by your friendly crew while the warm sea breeze carries the sounds of island music and laughter. The atmosphere is relaxed and festive, perfect for making new friends or sharing moments with loved ones. Expect a laid-back and enjoyable trip while unwinding with a refreshing beverage from the bar. As the last sliver of sun disappears below the water, watch for the green flash, an enchanting touch of magic. Sail back to Key West Harbor under the star-filled sky, creating a Key West memory to last a lifetime.
5.0(6)
1h 30m
Key West
- Free cancellation
From
$80
No similar experiences found
Viator
Exclusive Key Lime Pie Show and Tasting in Key West
A quick culinary adventure awaits at the Exclusive Key Lime Pie Show in the vibrant heart of Mallory Square. In just 30 minutes, discover the secrets to crafting the iconic Key lime pie, from mastering the graham cracker crust to achieving that perfect, creamy filling. After the lively demonstration, savor a slice of the world-famous pie, made without any green food coloring. Plus, take home the official recipe card to recreate this delicious treat at home, ensuring your taste of Key West lasts well beyond your visit.
5.0(1)
30 Minutes
Key West
- Free cancellation
- New
From
$32
No similar experiences found
Viator
Dolphin Watch, Snorkel, Open Bar & 1 Day Hop-On Hop-Off
This is the best 1 day combo where you will enjoy the water and land in Key West. Get to Hop On Hop off the conch train, one of Florida's most popular attractions, going to Truval Village: Steps away from the Ernest Hemingway Home and Museum, the Key West Lighthouse, the Southernmost Point and Key West Butterfly and Nature Conservatory. Start the day with a Catamaran adventure going Delphine watching and then snorkeling in 1 of the worlds largest reefs. We may even see sea turtle and other exotic fish. On the return enjoy and open bar that includes well mixed drinks, draft beer, margaritas, rum runners and a great selection of wine & champagne. As an added benefit join us at the Sails and rails museum to learn our history.
5.0(1)
1 Day
Key West
- Free cancellation
From
$150
No similar experiences found
Viator
Key West Craft Cocktail Experience
Explore the lively world of craft cocktails in a unique 1.5-hour session at Key West's oldest brick building. Get your hands on authentic bar tools to create two cocktails, while also sampling three others. Delight in tasty bites as you soak in tales of local legends like William Curry and the charming history that shaped this island paradise. With expert bartenders guiding you, this hands-on experience is perfect for anyone looking to mix it up while learning about Key West's vibrant past. Plus, take home some fun SWAG as a memento.
5.0(1)
1h 30m
Key West
- Free cancellation
From
$91
No similar experiences found
Viator
Key Lime Pie Walking Tour of Key West Historic Seaport
Taste the sweetest adventure in Key West—sunshine, stories, and the island’s most iconic dessert. Led by a Key West expert who’s part historian, part foodie, and fully obsessed with the island’s iconic slice, this small-group tour is a feast for all your senses. Wander the Historic Seaport while savoring three decadent Key Lime Pie tastings, each with its own tropical twist, and sip a refreshing Key Lime cocktail. Along the way, your guide shares insider tales, quirky legends, and secret local spots you won’t find in any guidebook. Fun, flavorful, and unforgettable—this is the Key West experience you’ll be raving about long after the crumbs are gone.
4.9(50)
1h 30m
Key West
- Free cancellation
From
$70
No similar experiences found
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
No similar experiences found
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
No similar experiences found
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
No similar experiences found
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
- Likely to sell out
From
$49
No similar experiences found
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
No similar experiences found
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(1875)
3 Hours
Key West
- Free cancellation
- Likely to sell out
From
$90
No similar experiences found
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
No similar experiences found
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
No similar experiences found
Viator
Key West Tiki Bar Boat to Popular Sand Bar with Turquoise Waters
Experience the Florida Keys like a true Conch! Our 4-hour Backcountry Sandbar Excursion takes you to a stunning location chosen by your captain based on the day's weather and tides. Immerse yourself in the intoxicating beauty of turquoise waters and deep blue skies. Keep an eye out for the incredible local wildlife – you might spot rays, turtles, fish, and even playful dolphins! Once we arrive at the sandbar, you'll have ample time to swim, soak up the sun, and simply unwind in this island paradise. Just bring your swimsuit, towel, sunscreen, and any snacks and drinks (including alcohol) you'd like to enjoy. This private trip is perfect for up to 6 passengers and runs daily from noon to 4 pm.
4.9(136)
4 Hours
Key West
- Free cancellation
- Private tour
From
$565
No similar experiences found
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
No similar experiences found
Viator
Key West Cooking Show Chef Demonstration with Meal
Looking for an unforgettable culinary experience? The expert chefs are passionate about sharing the unique flavors of Key West while keeping you entertained. Watch as they bring fresh, local ingredients to life with traditional cooking techniques and island flair. From savory entrees to irresistible tropical desserts, you’ll enjoy an interactive and delicious experience—topped off with a taste of paradise!
4.8(41)
1 Hour
Key West
- Free cancellation
From
$91
No similar experiences found
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
No similar experiences found
Viator
The Hemingway Experience in Key West
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.
4.8(53)
4 Hours
Key West
- Free cancellation
- Likely to sell out
From
$185
No similar experiences found
Viator
Key West Tiki Bar Sunset Cruise (by the seat) BYOB Adventure
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.
4.8(172)
2 Hours
Key West
- Free cancellation
- Likely to sell out
From
$81
No similar experiences found
Viator
Key West: Private Sunset Cruise on an Authentic Tiki Bar Boat
Key West is famous for it's sunsets and it doesn't get any better then on a private 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 tv and 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.
4.8(68)
2 Hours
Key West
- Free cancellation
- Private tour
- Likely to sell out
From
$457
No similar experiences found
Viator
Key West Sandbar Safari on One of a Kind Tiki Boat
Picture yourself aboard our unique tiki boat, the Lazy Lady, cruising through the crystal-clear waters toward a secluded sandbar. The sun is shining bright, and the air is filled with the scent of salt and sunshine. As you approach the sandbar, the boat glides over shallow waters, revealing stretches of soft, white sand inviting you to explore. Once you anchor, the fun begins! You can jump off the boat and wade into the warm, shallow waters, where the gentle waves lap at your feet. The atmosphere is relaxed, with laughter and conversation floating through the air. Some folks might set up beach games, while others enjoy swimming or soaking in the sun. Time seems to slow down as you enjoy this little slice of paradise, surrounded by friends or newfound acquaintances. Whether you’re collecting seashells, taking a dip, or simply lounging in the sun, a sandbar trip on a tiki boat is a perfect blend of relaxation and adventure.
4.7(128)
3h 30m
Key West
- Free cancellation
From
$139
No similar experiences found
Viator
Sweet Treats of Key West: A Tasty Walking Tour of Old Town
Discover the sweeter side of paradise on the Key West Sweets Tour! This fun and flavorful walking tour takes you through the heart of Old Town, along the harborfront and seaport, with stops at some of the best local spots for delicious donuts and sweet treats. Along the way, you’ll learn all about Key West’s rich and colorful history, from pirates and pioneers to artists and eccentrics. With plenty of photo-worthy moments, historic sites, and tasty bites, it’s the perfect outing for families, friends, and anyone looking to explore Key West in a unique and memorable way. Come hungry, bring your camera, and get ready to enjoy a one-of-a-kind tour through this tropical island treasure!
4.7(20)
1h 30m - 2 Hours
Key West
- Free cancellation
From
$70
No similar experiences found
