Activities in Key West · Page 3
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Activities
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From US$135Key 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!
From US$159Key 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.
From US$171.95Key West: All-Inclusive Watersports Adventure with Lunch & Beer
Get ready for the thrill of a lifetime with our Do It All Watersports Combo, the ultimate way to experience the best of Key West! Dive into 10 exhilarating activities packed into one unforgettable day: jet skiing, parasailing, snorkeling, banana boat rides, kayaking, paddleboarding, a water trampoline, an inflatable slide, a climbing iceberg, and a waterslide! Hop aboard the lively Party Cat and cruise to our floating waterpark paradise, where the sun and fun await you. If you choose the parasailing option, you’ll soar high above the stunning turquoise waters of the Florida Marine Sanctuary, taking in breathtaking views like never before! After an action-packed day, savor a delicious grilled lunch along with refreshing soft drinks and unlimited draft beer. This all-inclusive package offers the best value for watersports in Key West, and when you book directly with us, you’re guaranteed the lowest price!
From US$57.32Key West Rum and Reggae: Reef Snorkel Adventure and Sunset Sail
Fury’s Snorkel Adventure is unique for its combination of thrilling snorkeling and a vibrant sailing experience. Guests board a spacious Fury Catamaran, part of the largest luxury fleet in the Florida Keys, and sail to North America’s only living coral reef, all while enjoying the upbeat sounds of Reggae music. What sets this trip apart is the seamless blend of adventure and relaxation. Before snorkeling, the friendly crew provides expert assistance and instruction, ensuring everyone feels comfortable and confident. Once in the water, participants explore the stunning underwater world filled with pristine coral and diverse marine life. After the snorkeling adventure, guests can unwind with complimentary Rum Punch, Fury’s signature tropical beverage, along with beer, wine, and champagne. This perfect mix of excitement, stunning scenery, and leisurely relaxation creates an unforgettable day on the water!
From US$150.45Key West's Happy Hour Sandbar & Sunset Cruise - Unlimited Drinks
Key West’s ONLY Happy Hour Sandbar Party & Sunset Cruise! Get ready for the ultimate Key West experience—the only Happy Hour at the Sandbar & Sunset Cruise! This exclusive trip takes you to a beautiful sandbar, where you can lounge on our floating lily pads while our crew turns into your personal bartenders, serving up unlimited draft beer, mimosas, wine, and champagne. For those looking to explore, grab a snorkel and discover the underwater world teeming with tropical fish, stingrays, and other marine life. As the sun starts to set, we’ll cruise through the Florida Marine Sanctuary, giving you a front-row seat to Key West’s famous sunset—keep an eye out for dolphins, sea turtles & more! Savor a taste of Key West at the sandbar! Enjoy Cuban sandwiches, veggie wraps, fresh fruit, cheese & crackers, pita with hummus & more—all paired with unlimited beer, wine, mimosas & champagne. The perfect happy hour on a boat! Whether you’re here to relax, party, or explore, this trip has it all.
From US$85.95Parasailing in Key West at Smathers Beach
Parasailing at in Key West Fl at Smathers Beach Fly high over the Smathers Beach Key West as you parasail from State of the art parasail boats All crews Licensed and insured
From US$89Key West Sunset Sail: Dolphin Watching, Wine, and Tapas
Our Captain’s Choice Dolphin Watch Sunset Sail is the ultimate VIP sailing experience! Limited to an intimate number of passengers, this 2.5 hour sail is more like a private cruise than a group tour and is one of the top things to do in Key West. As we leave behind the Historic Seaport, look for Key West landmarks like the legendary Mallory Square, opulent Sunset Key and historic Fort Zachary Taylor. On reaching open water, the sails are unfurled and your adventure begins as your captain tracks dolphin pods to provide you an up-close view of these elusive creatures. With the dolphin viewing over, your cruise is just getting started! Grab a drink and relax as your captain positions the luxury catamaran for the perfect view of a famous Key West sunset. A chef’s selection of Tapas including shrimp cocktail are served during the sail. Choose your favorite drinks, including boutique wines and champagne perfectly paired with our Tapas – all included in the cost of your tour!
From US$64.13Key West Glass-Bottom Boat Tour with Sunset Option
Step aboard the Pride of Key West, the island’s only Glass Bottom Boat. This family-friendly tour invites you to explore North America’s only living coral reef* from our state-of-the-art 65ft catamaran. Glide over crystal-clear waters and enjoy unobstructed views of stunning coral formations, which support over 300 species of tropical fish, rays, and sea turtles. Our specially designed glass "windows to the reef" ensure continuous viewing for all passengers, allowing everyone to marvel at the rich marine life below. Relax in the air-conditioned viewing cabin or step out onto the large sundeck for panoramic views. Our knowledgeable guides provide insights into the coral reef ecosystem and highlight fascinating marine creatures. For a truly memorable experience, join our final trip of the day to watch the sunset as you return to port—an amazing way to cap off your Key West adventure! *In the event of unfavorable conditions, the captain may opt for an alternate location
From US$90.19Southernmost 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.
From US$64.45Parasailing over the Historic Key West Seaport
Parasailing at in Key West Fl at the Key West bight Fly high over the Key West Seaport as you parasail from State of the art parasail boats All crews Licensed and insured
From US$804.96Private Boat Charter Key West, Dolphin Tour, Snorkeling & Sandbar
Escape the crowds and discover hidden sandbars on a private eco tour through Key West’s backcountry waters. Swim, snorkel, or simply relax on pristine beaches only accessible by boat, with a flexible itinerary customized just for you. • Watch wild dolphins in their natural habitat • Private eco-friendly tour, just for your group • Cruise Key West’s beautiful backcountry waters • Flexible departure times to fit your schedule • Learn about marine life from a local guide
From US$284.95Key West Mini Catamaran Eco Tour
Get ready for an unforgettable journey that takes you through the natural beauty of Key West’s surrounding waters. Our Craigcat boat tour will take you on an exhilarating, up-close adventure across crystal-clear waters, winding through lush mangroves, stopping at pristine sandbars, and exploring hidden islands that are off the beaten path. This is your chance to experience Key West like never before — in a fun, fast, and eco-friendly CraigCat boat! Perfect for All Levels: Whether you're an experienced boater or a first-time adventurer, the Craigcat is easy to handle and designed for fun and comfort. With a small, nimble design, you’ll have the freedom to explore areas that larger boats or jet skis can’t reach. Up to 4 boats per tour. 2 guests max per boat. If you have 4 people in your group please make two separate bookings to accommodate your party and so forth up to 8 guests.