Sunset Sails

A local saying in Key West is “see you at sunset.” Throughout Key West’s history, dramatic sunsets have weaved their spell over visitors. Watching the sunset has become an integral part of everyday life in paradise. You may be asking yourself, the sun sets everywhere, what makes a Key West sunset so special? The answer to that question becomes apparent when you experience one for yourself.

The best place to watch the sunset in Key West is on the deck of a boat, drink in hand, wind in your hair and the sun slowly sinking into the ocean. There are many ships to choose from, whether you want a catamaran, sailboat or a schooner, we can make it happen.

Call your concierge today at 305-292-6266 or email to discuss your sunset cruise options.

Sailing Adventures

Take in a breathtaking sunset aboard a true sailing ship

Wine Tasting Sunset Sail

  • Sailing on a schooner
  • Up to 8 different varieties of wine
  • Craft and domestic beers available
  • Hors d'oeuvres complementing the wines
  • Explore the calm waters of the island's west coast

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Catamaran Cruises

Key West knows how to have a great time and nothing proves it more than cruising on one of our catamaran sunset sails!  Some feature live music, all feature open bars and a great time to be had!

Full Bar, Live Music & Appetizers

Enchant your evening with Key West's premier sunset sail on a spacious sailing catamaran. Feast your eyes on the beautiful Historic Seaport fading behind you while you enjoy premium drinks and appetizers. Sail past the jugglers and entertainers at the renowned Mallory Square Sunset Celebration. Gaze at opulent Sunset Key and historic Fort Zachary Taylor during your sailing tour of Key West landmarks.

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Live Music Sunset Cruise

Leave your worries behind and sail off into Key West’s famous sunset aboard a spacious state-of-the-art Catamaran. Dance along with premier musicians on the unforgettable “Commotion on the Ocean” Sunset Sail while you enjoy frosty margaritas, cold beer, wine, champagne and delicious appetizers.

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Private Charters

Whether you want a romantic sail or a large boat for your group, we can help you find the perfect charter

Call 305-292-6266 for further information regarding private charters

Private Sailing Catamaran

A breathtaking way to wrap up your day! On this exclusive private Sunset Sail, you sail through several extraordinary locations and watch the sun drop with the music of your choice creating a sonic landscape that matches the occasion. Enjoy some of your favorite adult beverages and appetizers.

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Dolphin Watch & Sunset

Find some dolphins and take some incredible twilight pictures as the sun sinks into the ocean

Dolphin Watch & Sunset Sail

Our Captain’s Choice Sunset Sail is a truly VIP sunset sailing experience! Limited to an intimate number of passengers, this three-hour sail is more like a private cruise than a group tour and is one of the top things to do in Key West.

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