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Top Key West Attractions & Tours

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Key West Sunset Sail Aboard Schooner

clock 2 hours
  • Enjoy an exquisite 2-hour sunset sailing adventure aboard a stunning modern-built schooner! Take in the sights aboard Schooner America 2.0, the most elegant schooner in Key West, as you sail by Mallory Square, Sunset Pier, Sand Key Light Tower and more. Enjoy complimentary beverages throughout your sail along with individually plated hors...Read more

Small-Group Key West Sunset Sail with Wine

clock 2 hours
  • Cruise into the sunset with wines from all around the world, imported and domestic beers as well as hors d'oeuvres. This cruise is great for a romantic evening or just to enjoy time with friends. Please arrive 30 minutes prior to your departure to check...Read more

Adults only Champagne Celebration Sunset Cruise from Key West

clock 2 hours
  • Get out on Key West’s beautiful shallow waters on the Adults Only sunset cruise, to sip Moët & Chandon champagne while enjoying the sunset. Included in the tour price are the house champagne Chandon Brut, 7 premium red and white still wines, 3 kinds of ice-cold beers and a champagne-inspired Gourmet Cheese Buffet (naturally gluten free) that...Read more

Key West Sunset Champagne Catamaran Cruise

clock 1 hour 30 minutes
  • Watch the famous Key West sunset on a 1.5-hour catamaran cruise. While you enjoy twilight views of the sea as the sun goes down, enjoy included wine, sparkling wine, beer, sangria or margaritas on board the boat. . As you sail through the water, admire views of the island with a cold beverage in hand — the perfect way to end a beautiful day in...Read more

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

clock 6 hours
  • Beautiful Key West is surrounded by sparkling blue waters of the Gulf of Mexico, making kayaking and dolphin watching the perfect way to spend a fun day in the sun. On the Island T’ing adventure, you’ll sail on a large catamaran away from the bustle of Key West, kayak among the natural backcountry mangrove islands in the Key West National...Read more

Key West Premium Sunset Sail aboard Schooner with Hors D'oeuvres and Full Bar

clock 2 hours
  • Picture the perfect Key West sunset, as you sail and sit on the deck of a romantic two-masted schooner. With the wind blowing in your hair, the tall ship sails into the sunset over the Southernmost Point of the U.S. Among the sights, your captain will take you past Mallory Square's Sunset Celebration and the Navy Mole where big ships dock....Read more

Key West Full-Day Power Adventure: Sailing & Watersports Package

clock 6 hours
  • This Key West experience lets you enjoy all that the island has to offer. Sail on a sleek catamaran along the smooth waters of the Gulf of Mexico and choose from several water activities, including kayaking around backcountry mangroves, snorkeling in the crystal-clear waters, parasailing along the world famous Key West waterfront, and more! A full...Read more

Key West Sunset Sail with Full Bar, Live Music & Hors D'oeuvres

clock 2 hours
  • Admire an exquisitely painted sky during this premium sunset cruise in Key West. Create fantastic memories as you set sail on one of Sebago's modern sailing catamarans while sipping sparkling wine or your favorite cocktail and feasting on shrimp cocktail on your way to the best sunset viewing spot. You'll enjoy twilight views of the island as you...Read more

Sunset Sip and Sail with Open Bar, Live Music, and Appetizers from Key West

clock 2 hours
  • Sunset Sip & Sail: Come see the legendary Key West Sunset on a Brand New Catamaran

    Sail Boat.
    • Open bar
    • Live Music
    • Great Appetizers

    Welcome aboard Key West's newest catamaran, the "Sandie Cat" as we literally sail off into the sunset. This trip includes live local music, great appetizers and an open well...Read more

Key West Snorkel and Sunset Sail: Rum n' Reggae

clock 3 hours
  • This Caribbean-themed trip offers two bucket list items that Key West is famous for - a tropical coral reef and amazing sunsets. Rum punch, lively reggae and a vibrant tropical island reef habitat await adventurers on this thrilling snorkel and sunset...Read more

Key West Wild Dolphin Sail and Shallow-Water Snorkel

clock 4 hours
  • Spend a beautiful Florida day out in the clear, blue waters on a snorkeling and dolphin-watching sailing excursion. Enjoy cruising on a roomy catamaran that books less than half their passenger limit for comfortable social distancing, spot wild dolphins hunting and playing with their babies, and snorkel shallow water coral reefs, wreck sights or...Read more

Key West Private Morning Sail on Schooner America 2.0

clock 1 hour 30 minutes
  • Enjoy a morning sailing experience and have Schooner America 2.0 all to yourself! Let us whisk you and yours away on a glorious morning sail across the beautiful waters of Key West on your own private yacht! This 1.5 hour charter aboard the America 2.0 grants you all the luxuries of yachting on your own private schooner. Let our crew do the work...Read more

Key West Sunset Sail on Traditional Schooner

clock 2 hours
  • The Tall Ship Schooner Jolly II Rover offers an exciting, traditional sailing experience - with a hint of Piracy! Yes - there are cannons! You will actually be sailing on the most photographed ship in Key West! The Rover is a replica of an early 1800's American Coastal Schooner. It is the only square rigged, topsail, gaff rigged schooner in the...Read more

Mimosa Day Sail aboard Schooner America 2

clock 1 hour 30 minutes
  • Take to the water on the fastest, most elegant sailboat in Key West, Schooner America 2.0. Namesake off the first sailboat to win the America's Cup in 1851, this stunning 105-foot sailboat features teak decks, mahogany trimmings and ample seating. Her 3,600 square feet of sail will propel you smoothly through the crystal green waters of Key West....Read more

Schooner Key West Day and Sunset Cruises with Full Bar

clock 2 hours
  • Experience sailing Key West on a majestic 2-masted schooner, just like adventurers from the 19th century, while enjoying the luxurious state-of-the-art accommodations of a modern passenger schooner. Her decks are spacious and comfortable. Feel the sense of adventure as the crew hoists the sails. Participate in this age-old tradition by helping...Read more

Sunset Sail in Key West with Beverages Included

clock 1 hour 30 minutes
  • Key West is famous for fabulous sunsets and Floridays is famous for our spectacular uncrowded champagne sunset cruise. Our reputation for personal service and attention to detail on our sunset cruise is legendary. Being out on the water for a Key West sunset is like being IN the sunset itself. There is nothing quite like it. Who knows, you may get...Read more

3-Hour Private Catamaran Sunset Sail of Key West with 1 Activity

clock 3 hours
  • Private sail with your friends, which can include either snorkeling, paddling or fishing, but always ends with some appetizers, drinks (BYOB) and a Key West Sunset!

    Private Single Activity Trip – Perfect to Play on the Reef or Just Sail and Enjoy the Sunset:

    Enjoy a traditional sailing charter Key West style, embarking from the...Read more

Key West Dolphin Watch Sunset Sail with Premium Wine, and Tapas Pairings

clock 2 hours 30 minutes
  • Our Captain’s Choice Dolphin Watch Sunset Sail is the ultimate VIP sailing experience! Limited to an intimate number of passengers, this 3 hour sail is more like a private cruise than a group tour and is one of the top things to do in Key West.

    As we leave behind the Historic Seaport, look for Key West landmarks like the legendary Mallory...Read more

Key West Sunset Snorkel Sail with Open Bar, Live Music, and Appetizers

clock 3 hours
  • Enjoy this 3 hour sunset combo trip. We will sail out to Key West’s best reef location, where you are welcome to jump in and enjoy an evening snorkel. If you do not feel like getting in the water, no worries, the bar is open! Grab a tropical mixed drink and dance to a live performance from one of Key West’s best entertainers while enjoying the...Read more

Key West Schooner Backcountry Eco-Tour: Sail, Snorkel & Kayak

clock 5 hours
  • Set sail aboard our classically-styled schooner as she departs Key West's Historic Seaport for a full day of sailing and exploration through the  pristine waters of the Gulf of Mexico.  Observe complex ecosystems and flourishing marine life as you snorkel the backcountry's own unique patch reef and kayak through centuries-old, uninhabited...Read more
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