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 a guided tasting of fine wines from around the world, along with a selection of craft and domestic beers and light hors d'oeuvres including crudites, meats, cheeses, crackers, fruit, and chocolate.

With small group sizes, there’s plenty of space to move around and enjoy the view without the crowds. It’s perfect for a romantic date or a fun evening with friends—upscale, but never uptight.

What really sets this trip apart is the crew. They’re fun, welcoming, and passionate about what they do—ready to pour your next glass, share a story, or make sure you’re having a great time. Add in a Key West sunset, and you’ve got one of the most unique and enjoyable evenings on the water!

Public transportation options are available nearby

Suitable for all physical fitness levels

Minimum drinking age is 21 years

Must be 13 or older for this trip.