Key West Sailing

Entice yourself with the starburst blaze of colors that is the Key West sunset on a luxurious sunset sail. See local landmarks and sail past Sunset Key and historic Fort Zachary Taylor as you dine on a tasty selection of varied hors d'oeuvres. Watch the sunset with your favorite drink in your hand and your loved ones by your side. Enjoy live music from local musicians! These are moments you’ll savor long after you leave town! Don't miss the boat. Book your spot today!

Experience the best afternoon you'll find on the straits of the Florida Keys by snorkeling this gorgeous coral reef. Climb aboard a luxurious catamaran as you cruise the crystal water to North America's only living coral reef. Dive into the sparkling, tropical water for underwater exploration, teeming with brightly colored tropical fish and corals. You don't have to be a jet setter to have a world-class time, so book your trip on this Coral Reef Snorkeling Catamaran Trip with Margaritas Included today!

Sail away with an ocean breeze for a night of music, drinks, and dancing on this Live Music Sunset Cruise in Key West, Florida. Experience some of Key West’s best musicians as you dance to the backdrop of a gorgeous, tropical sunset. Eat, drink, and be merry aboard a spacious and comfortable catamaran and take in all of the stunning sights and sounds. For an evening you'll want to last forever, set sail on this Live Music Sunset Cruise! Book your experience today!

Imagine yourself swimming in warm tropical waters with swarms of vibrant colorful fish all around you as you begin the day in the lap of luxury on an expansive 69’ sailing catamaran with Sebago Watersports. Sail seven miles off Key West’s majestic coast to the shallow Caribbean water of the Florida Keys Reef. Set off on this adventure and book your Morning Reef Snorkel with Sebago Watersports today.

Sail into an unforgettable Key West sunset while sampling beer, delicious hors d'oeuvres, and 8 fine wines from around the world. Rated one of the top two sunset tours in all of North America by Coastal Living Magazine, this luxurious Wind and Wine Sunset Sail on a historic Schooner will not disappoint. Make some new friends, enjoy tropical music, and delight your palate as you watch the sun melt into the water. Book your spot today!

Take an afternoon and plunge into the depths of Florida's coral reef for an amazing snorkeling experience. The Sandie Cat is Key West's newest snorkeling catamaran, which allows you to get to the reef with speed, comfort, and some serious style. Join the captain and crew, round up your group, and hit the waves for an unforgettable Key West experience packed with fun, sun, and tasty spirits. This all-inclusive trip boasts an open well bar including unlimited mimosas (mango, strawberry & orange) & a variety of soft drinks! Book your spot today!

Take an adventure into the depths to explore Florida's best reef on a snorkeling experience you will never forget! The Sandie Cat is Key West's newest and fastest snorkeling catamaran, which means less time wasted and more time for exploring the deep blue sea! Join the crew as they hoist the sail and get you and your family and friends out for a true Key West experience. Enjoy a complimentary breakfast, as well as unlimited mimosas (mango, strawberry & orange) & unlimited draft beer, in this all-inclusive snorkel experience. Reserve your spot today!

Explore the high seas in style on the Schooner America 2.0, the namesake of the first sailboat to win America's Cup in 1851. This stunning 105-foot sailboat features teak decks, mahogany trimmings, and ample seating for the whole family. The sights you’ll see along the way include a waterside view of Fort Zachary Taylor, the famed Sand Key Lighthouse, Mallory Square, and Sunset Pier. So sit back and feel the warm breeze dance across your skin as you watch the sights of the beautiful water around Key West. Book your spot today!

Set sail on Key West’s most elegant historic schooner, the When and If. Built in 1939 for General George Patton’s dream of sailing around the world “When and If” he was able, is available to the public for the first time in the yacht's lifetime. Sit back and experience the beautiful Key West sunset in style as the wooden schooner glides through the water driven by wind power alone. Meet the crew as they serve up a beautiful array of gourmet cheeses and share their stories of old Key West and the sea.

Spend a romantic evening aboard an authentic wooden schooner on this Windjammer Schooner Sunset Sail. This sailing vessel is fit for royalty, with its wide decks and ample seating and includes an open bar. Journey in comfort to landmark sites like the Navy Mole, Fort Zachary Taylor, Sunset Key, and more as the sails are hoisted and the tropical breeze whisks your cares away. Witness the beauty of a Key West Sunset and behold the grandeur of the star-filled Southern sky on this 2 hour pleasure cruise.

Immerse yourself in the tropical waters of Key West when you set out on a snorkel and sailing adventure. Watch swarms of colorful fish and marine wildlife swim around you as you explore the only living coral barrier reef in North America. The experienced captains will select the perfect reef based on the afternoon's water and wind variables so you can have the best snorkeling experience possible. See Key West's coral reef and book the Afternoon Reef Snorkel and Sail today!

Experience some morning snorkeling in the sparkling water of the Florida Keys on this Morning Coral Reef Snorkel Adventure & Catamaran Cruise. Climb on board a luxurious state-of-the-art catamaran and journey to a nearby reef teeming with tropical fish. Enjoy sightseeing around North America’s only living coral reef as you soak in the wonders around you. Book today for the ultimate snorkeling experience and catamaran cruise in Key West!

Have you ever wanted to take the wheel or hoist the sails of a real schooner? If so, here's your chance! This half-day Bugeye Backcountry Tour is an amazing mix of sailing, snorkeling, and kayaking among the most scenic settings in the Florida Keys, including the Sponge Garden Reef and Mangrove Island. Discover the amazingly diverse ecosystem of Key West’s backcountry and observe the abundant wildlife from the water. This tour is a MUST for outdoor enthusiasts! Book your spot today!

Experience snorkeling in the Florida Keys on an adventure like no other. Explore the crystal-clear water on this two-stop double-dip snorkel trip. Travel aboard the fastest catamaran around to explore North America's last coral reef. Dive in and venture out amongst the abundant marine life in 2 different locations with top-of-the-line provided snorkeling gear. Get acquainted with some of the most magical marine creatures as you swim around in their natural habitats during this underwater tour. Enjoy complimentary beer and wine served after. Book your experience now!