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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

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

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

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

Key West Dolphin Watch and Snorkel Cruise

clock 3 hours
  • Embark on a tranquil 3-hour cruise from Key West and make friends with one of nature's amicable mammals--the dolphin. Gaze at the scenic views while these playful creatures swim alongside your boat, then plunge into the Florida Keys' backcountry waters for snorkeling adventures. Uncover the captivating underwater world and observe a...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

Morning Reef Snorkel & Sail Adventure from Key West

clock 3 hours
  • . Come join us for a snorkeling journey to the only living coral reef in North America! We have some remarkable reefs on both the north and south sides of Key West that provide a distinct experience. It's an hour voyage out to the reef, you will stay there for an hour before we embark on our one-hour trip back to the dock. We offer...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

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