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Top Key West Boat, Cruises & Sailing 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

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

Small-Group Key West Sunset Sail with Wine

clock 2 hours
  • Sail off into the sunset with an array of international and homegrown wines, brews and hors d'oeuvres. Whether you're looking for a romantic evening or just some time to relax with friends, this cruise will be perfect. Please make sure to arrive 30 minutes before you set sail to check...Read more

Key West Mangrove Kayak Eco Tour

clock 2 hours
  • Alongside your veteran guide, you will leisurely paddle and discover the still, serene, azure-hued waters of the back country of Key West. You will cruise through the meandering mangrove waterways and traverse inches-deep depths, enabling you to easily observe and learn about the Keys' geography and its inhabitants from the coziness of your...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 Premium Sunset Sail aboard Schooner with Hors D'oeuvres and Full Bar

clock 2 hours
  • Imagine the ideal Key West sunset as you lounge on the deck of a romantic two-masted schooner. Feel the wind against your hair as the boat sails off into the sunset near America's Southernmost Point. As you admire the view, your captain will show you Mallory Square's Sunset Celebration and Navy Mole, where enormous ships dock.

    Treat...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

Key West Full-Day Island T'ing Eco-Tour: Sail, Kayak and Snorkel

clock 6 hours
  • Encompassed by the glistening azure waves of the Gulf of Mexico, beautiful Key West offers kayaking and dolphin watching as an amazing way to enjoy a day in the sun. With Island T’ing, you'll hop on board a large catamaran and set off from the hustle and bustle of Key West. Paddle through serene mangrove islands located within the Key West...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
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