Join us for Key West's Best Sunset Dinner Cruise. This 2 Hour trip Includes an amazing tropical food buffet, live music and open well bar. Climb aboard our custom luxury catamaran for a sunset trip out into the Key West sunset. As... 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

What makes Fury’s Live Music Sunset Sail unique is the combination of luxury and a vibrant, immersive experience. Guests embark on a spacious 65-foot catamaran, ensuring comfort and plenty of room to enjoy breathtaking views of ... 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

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

Step aboard the Pride of Key West, the island’s only Glass Bottom Boat. This family-friendly tour invites you to explore North America’s only living coral reef* from our state-of-the-art 65ft catamaran. Glide over crystal-clea... 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

Looking for the perfect way to end your day? Join us on the Seabreeze and ride in comfort with this relaxing, catered cruise into the horizon on Key West’s gentle seas. Relax in the shade under the bimini or sunbathe on the bow ... More

Key West is famous for it's sunsets and it doesn't get any better then on a private sunset cruise aboard our custom tiki bar boats. You and up to 5 guests will toast the sunset with your favorite libation(BYOB). Tours depart an ho... More

Key West is famous for it's sunsets and it doesn't get any better then on a private sunset cruise aboard our custom tiki bar boats. You and up to 5 guests will toast the sunset with your favorite libation(BYOB). Tours depart an ho... More

Embark on a tour around the island of Key West. Your guide will be talking you through many points of interest around the island. Make sure to keep an eye out for wildlife throughout the tour. About 20 minutes before the sunset, y... More

“The Key West Cocktail Cruise is the best thing to happen to Sunsets since cameras and sunglasses!” This is not your average Key West pleasure cruise.   Our 2 hour Key West Cocktail Cruise is what happens when true Hospita... 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

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... More

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 scho... More

Embark on an unforgettable journey as the sun dips below the horizon, casting vibrant hues across the endless expanse of the ocean. About Our Sunset Cruise in Key West is a magical experience where you'll witness nature's masterp... More

2 Hr. Private charter sailing from downtown Key West onboard Key West's First sailing charter boat, the pretty green sloop "High Tide" USCG Certified for up to 12 passengers, the Sloop High Tide and Sunset Sail Key West make for t... More

Please Note: Price of $695 is for up to 6 guests. Enjoy this private charter with friends or that special someone! Soak up the afternoon sun and cool off in the bright aqua waters of the Keys as you snorkel and explore Florida's a... More

Rent your own private yacht and savor the beautiful Key West sunset away from the crowds. Do it all on a luxury catamaran reserved just for you! Dolphin watch, jump off of the bows of the boat, sail along the Key West coastline, a... More