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

Summary

Key west schooner sunset sail wine tasting calm waters

You’ll step aboard a classic schooner in Key West for a small-group sunset sail with guided wine tasting and light hors d’oeuvres. Chat with locals or fellow travelers as you sample global wines (and beers too), all while watching the sky shift over calm water. The relaxed vibe and friendly crew make this more than just another day trip — it’s one of those evenings you’ll want to remember.

What’s the experience like?

Someone’s pouring a glass of chilled white as the sails catch that first bit of wind — it’s softer than I thought it’d be, almost quiet except for the water tapping the hull. Our guide, Mike (I think? He had that sun-faded baseball cap), grinned and asked if anyone wanted to try the “weird” Spanish red next. I was still working on my cheese plate, trying not to drop olives on the deck. The air smelled a little salty, but also like fresh bread from somewhere upwind. It’s funny how quickly you stop thinking about your phone out here.

We drifted past Mallory Square just as people started gathering for their own sunset rituals — someone waved, and one of the crew waved back with both hands. There were maybe fifteen of us on board, so you could actually move around without bumping elbows. I ended up talking with Li from Miami about how this wasn’t like any other day trip in Key West she’d done; she laughed when I tried to pronounce “hors d’oeuvres” properly (still not sure I nailed it). The wines kept coming — eight in total, from dry whites to something sparkling that tasted like apples and summer. Didn’t expect to like them all but…well, maybe it was the sea air.

The sky went pink-orange behind Sunset Key and everyone just sort of went quiet for a minute. Even Mike stopped telling stories and let us listen to the sails creak. It felt kind of rare — not showy or loud, just…good company and enough space to breathe. I still think about that view sometimes when things get noisy back home.

Step-by-step itinerary

Day 1 — Key West sunset sail with wine tasting

• Check in 30 minutes before departure
• Enjoy sailing with fine wines and hors d'oeuvres

Top questions

How many people are on the Key West sunset sail?

The tour is small-group only, so there’s plenty of space — usually around 15 guests per sailing.

What drinks are included on this sunset cruise?

The cruise includes eight different wines from around the world, plus craft and domestic beers, unlimited soft drinks, and water.

Are food or snacks served during the sail?

Yes, you get light hors d’oeuvres: meats, cheeses, crackers, crudités, fruit, and chocolate paired with the wines.

Is this sunset sail suitable for kids?

The minimum age is 13 years old; guests must be 21+ to drink alcohol.

Where does the Key West wine sail depart from?

You check in at their storefront half an hour before departure; location is central in Key West near public transport.

Is pickup included for this tour?

No hotel pickup is included; you meet at the storefront before boarding.

How long does the Wind & Wine Sunset Sail last?

The exact duration isn’t listed but it covers sunset hours each evening.

What’s included

Your evening includes check-in at a central storefront before boarding a historic schooner for a guided tasting of eight international wines (plus beer options), unlimited soft drinks, and generous hors d’oeuvres with meats, cheeses, fruit, crackers—even chocolate—all poured by a local crew as you watch sunset over Key West waters.