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 fea... More

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 K... More

The Wind & Wine Sunset Sail offers a boutique experience unlike any other in Key West! This isn’t your typical party boat—it’s a calm, uncrowded sail aboard a historic schooner with an intimate, relaxed vibe. You’ll enjoy ... More

Our afternoon dolphin watch is limited to an intimate number of passengers to optimize your views! Enjoy sailing aboard a 60' catamaran to the dolphin playground to view wild dolphins play and frolic in their natural habitat. Atla... More

Rise and Reef Key West Snorkel Trip on The 65 foot custom built Sandie Cat. Your 3 hour snorkel trip will start with a Light Breakfast and sail to the Key West living reef where you will see coral and tropical fish. All snorkeling... More

Our Captain’s Choice Dolphin Watch Sunset Sail is the ultimate VIP sailing experience! Limited to an intimate number of passengers, this 2.5 hour sail is more like a private cruise than a group tour and is one of the top things ... More

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... More

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 comf... More

Dip and Sip Key West Snorkel Trip on The 65 foot custom built Sandie Cat. Your 3 hour snorkel trip will start a sail to the Key West living reef where you will see coral and tropical fish. All snorkeling equipment is provided an... More

The Sunset Watersports Dolphin watch triple combo is the best way to watch Dolphins, Snorkel the Key West tropical waters, and see the world famous Key West Sunset all in one trip.... More

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 thr... More

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 ... More

There's no better way to savor the magic of a Key West sunset than aboard a majestic schooner, complete with a full open bar. This enchanting journey blends the timeless elegance of traditional sailing with the lively spirit of Ke... More

Avoid the crowds and Sail on Key West’s beautiful shallow waters on this Adults Only Sunset & Moët cruise, to sip Moët & Chandon champagne and indulge your palate while being washed in the colors of the Key West sunset! Incl... More

All while avoiding the crowded big boats, spend part of your Florida vacation day out on the tropical waters of Key West on Catamaran Echo - making vacation memories since 1991. Enjoy a premium shallow snorkeling and dolphin-watc... More

Embark on an adventure off the shores of Key West, where the turquiose waters of the Gulf of Mexico and the Atlantic Ocean meet in a symphony of beauty and tranquility. Your day begins as you board a luxurious catamaran, your vess... More

Aboard our spacious 42-foot sailing catamaran, you'll experience the pure joy of sailing as the lightweight boat glides across the water, catching every gust of wind. This tour is perfect for all ages and offers a wide-open, unob... More

Get out to the Key West barrier coral reef in style on a former luxury sailing catamaran yacht now licensed for 30 passengers, but with only 17 passengers maximum. Avoid the crowds and enjoy sailing, coral reef snorkeling and the ... More

This private charter is designed for a relaxed, flexible day on the water, perfect for groups who want a casual, unstructured experience. Instead of a formal, guided eco-tour, this trip offers a more laid-back vibe, allowing you t... More

Departing from Key West’s Historic Seaport, the Appledore Star’s sails are raised for an authentic sail experience on the way to Key West’s backcountry. Your day is spent exploring Key West’s uninhabited mangrove islands... More