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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

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 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

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

Luxury Sailing Catamaran - Private and Group Charters

clock 2 hours
  • If you're looking for something more private than the large, crowded boats, look no further than our luxurious 44-ft catamaran, exclusively reserved just for you. Snorkel the best reef in Key West while soaking up the sun's rays on one of our trampolines or jump off the boat into crystal clear turquoise waters with a cocktail in hand....Read more

Private Looe Key Snorkel from Big Pine Key

clock 3 hours
  • The Looe Key Marine Sanctuary is a part of the Great Florida Reef, which is the only coral reef in the continental United States and ranks third amongst barrier reefs worldwide; behind Australia's Great Barrier Reef and Palancar Reef in Mexico/Belize. It is a great place for snorkelers to...Read more

The Original Key West Island Jet Ski Tour from the Casa Marina

clock 1 hour 30 minutes
  • Billy began his Original Island Jet Ski Tour back in 1992. There have been plenty of others that have tried to imitate, but there is only one true original! Our guides are certified and live on the island, so they know these waters like their own backyard - because it really is!

    We adjust our tour route based on the weather and waves...Read more

Glass Bottom Boat Island Eco Adventure

clock 3 hours 30 minutes
  • Max 6 people can embark on a journey of exploration in the Looking Glass, our 28' glass bottom boat. This vessel allows you to craft your own adventure, be it snorkelling at the reef, investigating an offshore island, searching for dolphin and other sea creatures or simply taking pleasure in lounging on a sandbar with your feet partly...Read more

Private Key West Sunset Sail

clock 2 hours
  • Please note: price is for up to 6 guests. The perfect Key West sunset sail - peaceful, private and exclusive! Your captain and mate will take you out to watch the sunset from your own private classic sailing vessel, with soft drinks with ice provided for any adult beverages you choose to...Read more
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