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Top Key West Water 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

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 Sunset and Cocktail Cruise with Open Bar

clock 2 hours
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    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

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 Sunset Cruise with Live Island Music

clock 2 hours
  • Set sail on the salty sea and listen to some of Key West's greatest musical acts, all while taking in a breathtaking sunset. Join us for an unforgettable evening with food, drinks and live music as we watch the sun dip below the horizon. So take someone by the hand and let the music carry you away on this amazing Key West Sunset...Read more

90 Minute Tour of Key West Jet Ski Adventure

clock 1 hour 30 minutes
  • For all you thrill-seekers and explorers, our guided Jet Ski Tours are a great way to experience Key West. Let our guide take you on a 90-minute adventure around the entire island. This 27-mile exploration is a feast for the eyes and senses. We'll make several stops along the way, checking out all of the best-known attractions the island has...Read more

Key West Fishing 10am-4pm Daily

clock 6 hours
  • Since 1947, we have been the longest running deep sea fishing charter in Key West, Florida. Our 58-foot boat is inspected twice yearly by the US Coast Guard and is equipped with amenities such as restrooms, a galley serving snacks, and experienced Captains to assist anglers. Get your catch of the day on board our vessel - you can keep them or...Read more

Key West Sunset Dinner Cruise with Tropical Buffet

clock 2 hours
  • Come join us for the best sunset dinner cruise in Key West! Climb aboard our luxury catamaran and be mesmerized by the magnificent views of the setting sun. Our onboard chef will prepare an array of delicious tropical cuisine including Caribbean Roast Pork, Black Beans and Rice, Deep Fried Sweet Plantains, Grilled Marinated Chicken with...Read more

Private 2-Hour Tiki Boat Party in Key West

clock 2 hours
  • Climb aboard our tiki bar boat and bring up to 5 friends for a two-hour cruise to an idyllic sandy bottom anchorage. Leave the driving to your captain while you enjoy the shade from the thatched roofs and soak up some rays on our 6' x 18' floating mat! Don't forget your favorite cocktail, snacks, and fun-loving pals - plus, there's a walk-in...Read more

Key West Glass-Bottom Boat Tour with Sunset Option

clock 2 hours

  • View the only living coral barrier reef in the continental United States on this two-hour glass-bottom boat journey from Key West! Enjoy a relaxing cruise while looking down to see an abundance of marine life below, such as tropical fish, hard and soft corals, sponges, snails, jellyfish, anemones, crabs, lobsters, rays, sea turtles, nurse...Read more

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