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 Cool Key West three years running. See the sunset on a beautiful 65ft sailing boat.
Highlights
- Rated #1 on Cool Key West 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 Cool Key West 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
- Not wheelchair accessibleThe marine head (restroom) requires navigating steps to access.
- Vessel has a toilet
- Paid parking nearbyIf you are going to park your car downtown, give yourself an extra 20 minutes to be on the safe side.
- Suitable for travelers of all fitness levels
- 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
(11)Q: What food and drink is served on Wind & Wine?
A: The crew announces and generously pours eight wines: four red, three white, and a Champenoise throughout the sailing. You can enjoy everything in this “wine tasting” format or stick with one that just “hits the spot.” Five different imported and domestic beers, as well as cans of soft drinks and filtered drinking water, are also served. Charcuterie boards are served throughout the cruise and include a rolling selection of meats, cheeses, crackers, fruit, crudités, and chocolate. Choices include Havarti dill, smoked Gouda and summer sausage, caprese skewers, water crackers with Brie, green apple with a honey drizzle, to name a few. Read more Dec 2024
Traveler Photos
Reviews
Average 4.95 out of 5 stars based on 1,407 traveler reviews collected by Cool Key West and partner sites such as Cool Destinations and TripAdvisor
Additional Info
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Frequently Asked Questions (11)
The answers provided below were previously given in response to questions from Cool Key West customers.
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The crew announces and generously pours eight wines: four red, three white, and a Champenoise throughout the sailing. You can enjoy everything in this “wine tasting” format or stick with one that just “hits the spot.” Five different imported and domestic beers, as well as cans of soft drinks and filtered drinking water, are also served.
Charcuterie boards are served throughout the cruise and include a rolling selection of meats, cheeses, crackers, fruit, crudités, and chocolate. Choices include Havarti dill, smoked Gouda and summer sausage, caprese skewers, water crackers with Brie, green apple with a honey drizzle, to name a few.
Dec 2024Yes, we can accommodate you. If you have any specific dietary restrictions or follow a vegetarian or vegan diet, please inform us by mentioning it in the “booking notes” section when making your reservation. The crew will do their best to provide suitable alternatives whenever possible.
You are also welcome to bring your own food aboard.
Apr 2025Yes, restrooms are located in the building at the Dock Master’s Office.
Mar 2022Yes, by nature of the sails, there is plenty of shade on board. In the summer months or when the wind is minimal, we can add a canopy for shade.
Feb 2022No, there is no WiFi available.
Dec 2021- For a full refund, you must cancel at least 24 hours before the charter start time.
- If you cancel less than 24 hours before the charter start time, the amount you paid will not be refunded.
- Any changes made less than 24 hours before the charter start time will not be accepted.
- Cut-off times are based on the charter local time (EDT).
- 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!.
The minimum age for this charter is at your discretion and 21 to drink alcohol.
Apr 2025If a date or time is not listed on the calendar, it’s sold out or unavailable for another reason. Support cannot assist further if a date or time is not on the calendar.
If you find a date and time that works for you, book it NOW because things always sell out at this time of year.
Apr 2025Accessibility information for the Key West Private Wind & Wine Charter (for up to 30 guests) is as follows:
- Not wheelchair accessible
- Suitable for travelers of all fitness levels
Detailed check-in instructions – including meeting point address, Google map, and parking information – for Key West Private Wind & Wine Charter (for up to 30 guests) will be included in your confirmation email from Cool Key West. Please be sure to double and triple check your email address is correct at checkout so this important email makes its way to you!
Mar 2024What'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!
Additional Info
- Confirmation is instant and will be received at time of booking
- Not wheelchair accessibleThe marine head (restroom) requires navigating steps to access.
- Vessel has a toilet
- Paid parking nearbyIf you are going to park your car downtown, give yourself an extra 20 minutes to be on the safe side.
- Suitable for travelers of all fitness levels
- 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
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