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Sunset cruises in Key West are one of the island’s defining rituals, marking the moment when the light softens and the day begins to let go. As the horizon settles into warmer tones, being on the water invites you to slow down and stay present rather than move on to the next thing.
The cruises and sails on this list offer different ways to experience that pause, from quiet trips that follow the wind and open water to relaxed outings with a drink in hand and the shoreline drifting behind you. However you choose to spend it, sunset in Key West is less about spectacle and more about the calm it creates.

A guided tasting of fine wines from around the world, with select beers and light bites including meats, cheeses, fruit, and chocolate.

Sunset sailing on the historic schooner Appledore, where classic seamanship and a slower pace define the experience. Beer, Wine, Liquors and hors d'ouvres are served aboard.

A classic schooner sail at sunset, paired with champagne and front-row views of Key West’s evening skies.

Sunset sailing on the historic schooner Appledore, where classic seamanship and a slower pace define the experience. Beer, Wine, Liquors and hors d'ouvres are served aboard.
Some links on this site are affiliate links, which means I may receive a small commission at no extra cost to my guests. This is standard in the industry and never influences my recommendations — I only share experiences I genuinely trust to deliver a premium experience.
KEy West, Florida
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