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Top Key West Attractions & Tours

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Sunset Sail Cruise in Key West

clock 120 minutes
  • Sailing on the Rover is an exciting, traditional sailing experience with a Hint of Piracy! Yes - We have cannons! Come sail on Key West's most photographed ship! The Schooner Jolly II Rover is the only squared rigged, topsail schooner in the Historic Seaport! It is Key West's famous "Red Sails in the Sunset" Tall Ship! There is no band playing or...Read more

Gulf of Mexico Sunset Kayak Tour of Key West

clock 2 hours
  • We are the only Kayak business on Stock Island's Gulf side that offers direct access to the Gulf, allowing patrons to witness a stunning sunset without...Read more

4-Hour Private Sand Bar Cruise on a Tiki Bar Boat in Key West

clock 4 hours
  • Party like a local by visiting one of the Florida Keys' Back Country sand bars. Your knowledgeable captain will choose the optimal location based on conditions, leading you to breathtaking turquoise waters and vivid blue skies. You may be lucky enough to spot rays, turtles, fish, or even dolphins while there! Don't forget your swimsuit,...Read more

Sunset Tiki Boat Tour in Key West

clock 2 hours
  • Key West is renowned for its spectacular sunsets, and they can't be beat when experienced from a private sunset cruise on board our custom tiki bar boats. Accompanied by up to 5 of your friends, you will be able to raise a toast to the setting sun with your preferred beverage (BYOB). We set sail an hour and fifteen minutes before sundown so...Read more

Adults only Champagne Celebration Sunset Cruise from Key West

clock 2 hours
  • Escape to the stunning shallows of Key West on an Adults-Only Champagne Celebration Sunset Cruise, where you can savor Moët & Chandon champagne while admiring the sunset. The tour cost includes house champagne Chandon Brut, 7 varieties of red and white still wines, 3 types of ice-cold beers and a gluten-free Gourmet Cheese Buffet featuring 4...Read more

Key West Craft Cocktail Crawl

clock 3 hours
  • Come along with us on a delicious tour through Key West, as we visit 5 of its craftiest bars and most secret local spots. Sample five local cocktails, paired perfectly with two food tastings, to get an authentic taste of the island life! Hear the unique stories behind some iconic drinks like the Hemingway Daiquiri, and explore tiki-era...Read more

Guided Bicycle Tour of Old Town Key West

clock 3 hours
  • Embark on a journey with us for a remarkable and unforgettable Key West experience! Your own local guide will show you the islands' top sights. Sail through Old Town, explore famous landmarks, and listen to tales about the interesting people who have lived in Key West. Our leisurely 2.5 hour ride is great for both you and our stunning...Read more

Half-Day Cruise from Key West with Kayaking and Snorkeling

clock 4 hours 30 minutes
  • Don't miss out on one of the best activities Key West has to offer—a half-day sailing tour that takes you through the waters of the Florida Keys. During your cruise, you'll have a chance to kayak in a mangrove eco-system and spot various birds, followed by snorkeling in the crystalline sea. Snacks, beer, wine, and use of...Read more

Private Key West Historic Homes and Island History Walking Tour

clock 2 hours
  • Tripadvisor ranked our tour as the top 10 history tours in North America for 2022. Our award-winning guides will take you on a memorable 2.25 hour stroll through the captivating Old Town district of Key West, home to many historic homes and iconic architectural edifices that have long been part of the culture and folklore of this remarkable...Read more

Key West Sushi Sunset Cruise

clock 2 hours
  • Looking for an enjoyable way to conclude your day? Come join us on the Seabreeze and sail in comfort with this calming, catered cruise across the Key West horizon. Enjoy a bit of shade under the bimini or bask in the sun from the bow as you take in one last glimpse of daylight. Sunset Cruises are a prized experience in Key West with...Read more

Key West Southernmost Food and Cultural Walking Tour

clock 3 hours
  • Sample: Indulge in a flavor of Key West during this 3-hour culinary walking tour, guided by a specialist. Visit 5 local "mom and pop" stores in historic old town, sampling typical Cuban cuisine, seafood from the area, and the iconic Key Lime Pie. Food samples are sufficient for a satisfying lunch. As you wander away from the touristy streets...Read more

Key West Historic Seaport Food Tasting and Cultural Walking Tour

clock 3 hours
  • Uncover the flavors of the ocean on this guided 3-hour culinary journey around Key West. Savour maritime heritage with scrumptious seafood (or non-seafood options) cuban sandwich & key lime pie tastings. Relish classic ingredients like Key West pink shrimp, Caribbean warm-water lobster, and fresh fish. Sample white wine after walking through...Read more

Key West Sunset and Cocktail Cruise with Open Bar

clock 2 hours
  •  

    The Key West Cocktail Cruise is an absolute must for anyone looking to experience the most amazing Sunsets that Key West has to offer - it's better than cameras and...Read more

Key West Sunset Sail Aboard Schooner

clock 2 hours
  • Relish in a magnificent two-hour sunset voyage on board a breathtaking modern schooner! Witness the majestic sights of Key West from Schooner America 2.0, the most exquisite schooner around, as you sail past Mallory Square, Sunset Pier, and Sand Key Light Tower and more. While indulging in complimentary libations, savor individually prepared...Read more

Group Sunset Cruise from Duck Key

clock 1 hour 30 minutes
  • The Solé Watersports Sunset Cruise at Hawks Cay Resort is the only Sunset Cruise in the Duck Key area. It includes cruising along the resort and homes of Duck Key, into open water and over to the uninhabited islands of Tom's Harbor. During the cruise, we'll watch for coastal birds hiding in the mangroves, pods of dolphins, and other sea life...Read more

Dolphin Watching and Snorkeling Adventure in Key West

clock 3 hours 30 minutes
  • Observe bottlenose dolphins as they frolic in their natural environment on a Key West dolphin excursion. Afterwards, take a voyage to the backcountry for some exhilarating snorkeling. Hunt for marine creatures and underwater plants like coral formations and more.

    We're locals, so our captains are familiar with the waters around Key...Read more

2-Hour Private Sunset Cruise on Tiki Bar Boat in Key West

clock 2 hours
  • Key West is renowned for its breathtaking sunsets, and they are even more spectacular when viewed from a private sunset cruise aboard one of our custom tiki bar boats. Accompanied by up to five guests, you can cheers the setting sun with your favorite beverage (BYOB). Tours depart an hour and fifteen minutes before sunset in order to find the...Read more

Sunset Sail on Historic Schooner in Key West

clock 2 hours
  • Set sail for a beautiful Key West sunset on the historic schooner When And If! Commissioned by then Colonel George Patton "When the war is over and if I return, Bea and I will sail around the world!" Step foot on the gorgeous teak decks, help raise sail, take a turn and the wheel or sit back and relax as Sunset Sail Key West does what it's best...Read more

Parasailing at Smathers Beach in Key West

clock 1 hour
  • . Soar above the waters of Smathers Beach in Key West, Florida from the safety of a state-of-the-art parasail boat. All crew members are licensed and insured for your...Read more

Key West Sunset Champagne Catamaran Cruise

clock 1 hour 30 minutes
  • Witness the renowned sunset over Key West from a 1.5-hour catamaran sail. While you bask in the dusk vistas of the ocean as the sun sets, sip some complimentary wine, champagne, beer, sangria or margaritas on board the vessel. As you cruise across the water, appreciate sights of the island with a chilled beverage in hand — an ideal way to...Read more

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