Key West Wind & Wine Private Charter (up to 30 guests)
Overview
The Wind & Wine Key West Sunset Sail has been honored with a #1 rating on Key West Water Sports three years running. See the sunset on a beautiful 65ft sailing boat.
Highlights
- Rated #1 on [BRAND] for three years running
- Beautiful sailing boat
- Exclusive Trip with just over twenty passengers
- Amazing Key West sunset views
- Attentive and Friendly Crew
Description
The Wind & Wine Key West Sunset Sail has been honored with the #1 rating on [BRAND] for so many years we've lost count. Wind & Wine is an incomparable sunset experience amid the warm tropical caribbean waters of the Florida Keys.
Rated a Top Sunset Cruise in North America by Coastal Living Magazine, the Wind and Wine Sunset Cruise is unparalleled for folks who want an upscale, yet relaxed and intimate, sunset sail. Sailing nightly, we serve eight different fine wines from all over the world, usually four red, three white, and a Champagne.
Wine drinkers love this cruise, since it is virtually the only sailing excursion in the U.S. that serves “real” wine. In addition, an array of quality beer, and hors d’oeuvres are also served, making the evening an unforgettable start to a great Key West night!
Choose from up to 8 different types of wine from around the world (taste through them all, or focus on your favorites). Choose from 5 different types of imported and domestic beer. Enjoy a wonderful variety of delicious appetizers like Havarti Dill, Smoke Gouda and Summer Sausage, Caprese Skewers, Water Crackers with Brie, Green Apple with a Honey Drizzle, and more.
What's Included
- Sunset Sail Aboard a Modern Style Schooner
- Fancy Cheeses, Crackers, and Fruit
- Premium Wine
- Imported and Domestic Beer
- Sodas and Bottled Water
- Gratuity is included — no tipping on the night!
What To Expect
5-Star Resort (check-in)
After a quick and easy check-in, you’ll embark on a beautiful 65 ft Skipjack schooner.
15 Minutes (approx.)
Sailing
As we sail through the stunning waters of Key West, kick back and enjoy the views. The beauty of the Florida Keys will surround you, and you might even spot a dolphin or two along the way!
1 Hour 55 Minutes (approx.)
Food & Drinks
You can choose from up to 8 different types of wine from around the world (taste through them all or focus on your favorites). You can also choose from 5 different types of imported and domestic beer. You can also enjoy a wonderful variety of delicious appetizers like Havarti Dill, Smoke Gouda and Summer Sausage, Caprese Skewers, Water Crackers with Brie, Green Apple with a Honey Drizzle, and more.
Enjoy The Key West Sunset
Sailing into the Key West sunset is a breathtaking experience that perfectly captures the magic of this tropical paradise. As the sun dips below the horizon, the sky transforms into a canvas of fiery oranges, soft pinks, and deep purples, reflecting off the tranquil waters of the Gulf of Mexico. Key West's unique position at the southernmost tip of the continental U.S. offers an unobstructed view of this daily spectacle, often accompanied by the silhouette of dolphins or seabirds in the distance.
Additional Info
- Confirmation is instant and will be received at time of booking
- What to bringCamera, comfortable shoes, sunglasses, sunscreen, and a smile!
- The minimum age for this charter is at your discretion and 21 to drink alcohol
- This charter will have a maximum of 26 passengers
Frequently Asked Questions
(10)Q: What food and drink is served on Wind & Wine?
Cancellation Policy
Still have questions?
We're here to help.
Activity code: C-757
Traveler Photos





Reviews
Average 4.95 out of 5 stars based on 1,690 traveler reviews collected by Key West Water Sports and partner sites such as Cool Destinations and TripAdvisor
Additional Info
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