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, admi...

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 ...

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 suns...

Sail aboard the fastest and most elegant schooner in Key West, Schooner America 2.0! This boat is a replica of the 1851 Schooner America that won the first America's Cup Race in 1851. Admire her beauty on the clear, calm Caribbean waters while sippin...

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 Wes...

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 s...

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 cock...

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 kin...

Join us for a snorkel adventure to the only living coral reef in North America. We have several fantastic reefs to choose from on both the north and south sides of Key West, each offering a unique experience. It’s about an hour trip out to the reef...

Join us for a snorkel adventure to the only living coral reef in North America. We have several fantastic reefs to choose from on both the north and south sides of Key West, each offering a unique experience. It’s about an hour trip out to the reef...

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...

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 dolph...

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 wil...

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 m...

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 ch...

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 bus...

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 ...

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...

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 ...

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...