Key West Small-Group Sunset Sail with Wine and Hors d'oeuvres

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, relax

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!

From: $0.00

Location: Key West

What's Included

Community Discussion

Q&A

Q: Are there any age limits for this sunset sail experience in Key West?

A: Yes, while the experience is geared towards adults, children are welcome if they're accompanied by an adult. Just keep in mind that it's mainly a wine tasting and the vibe is pretty relaxed, so it might not be super fun for younger kids. If you're thinking of bringing children, maybe check with the provider first to see if they have any specific recommendations.

Q: What should I wear for the sunset sail? Is it casual or more dressy?

A: The vibe is pretty laid-back, so casual attire is totally fine. Many people wear shorts or sundresses, but you might want to bring a light jacket for when the sun goes down. Just remember, you're on a boat, so comfy shoes are a plus! If you're planning to drink wine, maybe avoid anything too fancy that you wouldn’t want stained.

Q: How's the parking situation at the dock for the sunset sail?

A: There are a few public parking lots near the dock, but they can fill up quickly, especially during tourist season. I’d recommend arriving at least 30 minutes early to find a spot. If you don’t mind walking a bit, there are cheaper lots a little further away. Also, keep in mind that you'll have to carry your stuff, so pack light!

Discussions

Just got back from the Wind & Wine Sunset Sail! Absolutely loved it!

Wow, just wow! My partner and I went on the sunset sail last weekend, and it was one of the best experiences we've had in Key West! The crew was super friendly and the wines were just amazing. We also loved the light hors d'oeuvres, especially the cheese platter. The sunset views were breathtaking! We booked it through Danger Charters, and everything went so smoothly. Highly recommend for a romantic evening!

Thinking of gifting the sunset sail experience—any tips?

I’m considering giving the Wind & Wine Sunset Sail as a gift for my parents' anniversary. They love wine and sunsets! Has anyone done this? Any tips on how to make the experience extra special for them?