Key West Sunset Sail with Wine Tasting: Small-Group Schooner

★★★★★★★★★★ 4.92 (1,478 reviews) 95% rated it 5 stars

Free cancellationTravelers' pick

1/13

Duration2h

GroupUp to 26

LanguagesEN

Mobile ticketAccepted

Eight wines, a calm schooner, and the Key West sunset without the party boat rush

The Wind & Wine Sunset Sail is a small-group sailing tour in Key West aboard a historic schooner, where you taste fine wines from around the world, sample craft and domestic beers, and eat light hors d'oeuvres while watching the sunset over the water. The crew handles everything—wine service, stories, timing—so you show up 30 minutes before departure and spend two hours on the water without arranging a thing. Minimum age is 13; you must be 21 to drink alcohol.

Step-by-step itinerary

Sunset sail with wine tasting

Check in 30 minutes before departure
Enjoy sailing with wine and hors d'oeuvres

The Experience

If you land in Key West with a free afternoon or an evening to fill, this sail solves the problem of finding something that feels special without the noise of a party boat. You check in at the storefront 30 minutes before departure, then board a historic schooner built for the kind of sailing where you can actually talk to the people you came with. The boat stays small—that's the whole point—so there's room to move around the deck, lean on the rail, and watch the light change without standing shoulder-to-shoulder with strangers.

The wine is the real draw here. The crew pours eight different wines from around the world—usually four reds, three whites, and a Champagne—which is rare on any sailing excursion in the U.S., let alone one on the water. If wine isn't your thing, there's craft beer, domestic beer, and soft drinks, all unlimited. The hors d'oeuvres change with the wines: crudités, meats, cheeses, crackers, fruit, and chocolate. Nothing fancy or fussy; it's the kind of food that makes sense with a glass in your hand and the horizon in front of you. The crew knows what they're doing—they're there to pour, to talk, to make sure the evening works. Two hours is long enough to feel like a real escape and short enough to fit into an evening that already has plans.

What’s included

Two hours of sailing aboard a historic schooner.
eight fine wines from around the world with unlimited craft beer, domestic beer, and soft drinks.
light hors d'oeuvres including crudités, meats, cheeses, crackers, fruit, and chocolate.
crew service throughout.

Good to know

Easy physical levelPublic transport nearby

Operated by Danger Charters

Is this one for you?Book this sail if you want a real sunset over water without the noise and crush of a party boat. The small group size and the crew's focus on the experience—not the headcount—make the difference for anyone looking for an evening that feels intentional instead of generic.