Key West Wind & Wine Sunset Sail
Overview
Wind & Wine has been the #1 rated sunset sail on Cool Key West for over a decade. In our opinion, this is the best wine tasting sunset cruise in the United States and is a Key West "must do."
Highlights
- The #1 rated Key West sunset cruise for over a decade
- Premium wine, ice cold beer, and yummy hors d’oeuvres
- The trip feels exclusive, with just over twenty passengers
- Spectacular views of the Key West sunset
- Attentive and friendly crew (you'll see it's VERY obvious they love their job)
Why Travelers Choose This Activity
The best sunset sail in Key West by a mile, and, quite possibly, all of the United States.
Description
The Wind & Wine Key West Sunset Sail has been honored with the #1 rating on Cool Key West for over a decade. 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. Wine drinkers love this cruise, since it is virtually the only sailing excursion in the US that serves “real” wine.
Sailing nightly, the crew announces and generously pours eight wines: four red, three white, and a Champenoise. You can enjoy everything in a structured "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 bottled water, are also served.
Charcuterie boards are served throughout the evening 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.
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. Guests are also welcome to bring their own food aboard.
What's Included
- Yummy hors d’oeuvres, paired nicely to the wines, are served throughout
- 8 premium wines, all poured generously
- 5 imported and domestic beers
- Cans of soda and bottled water
- Gratuities
What To Expect
5-Star Resort (check-in)
After a quick and easy check-in, you’ll embark on a modern, yet beautiful, 65 ft skipjack schooner.
15 Minutes (approx.)
Sailing
As you sail out of the harbor past boats crammed with 100+ people, you will thank yourself for making a good decision on how to spend your evening. Good job! Now 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
The crew announces and generously pours eight wines: four red, three white, and a Champenoise. You can enjoy everything in a structured "wine tasting" format or stick with one that "hits the spot." Five different imported and domestic beers and lagers, as well as cans of soft drinks and bottled water, are also served.
Hors d’oeuvres, in the form of charcuterie boards, are served throughout the evening and include a varying 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.
Enjoy the spectacular 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. A sensational pairing with your wine tastings!
Additional Info
- Confirmation is instant and will be received at time of booking
- What to bring: camera, comfortable shoes, sunglasses, sunscreen, and a smile!
- The minimum age for this activity is 13 to attend and 21 to drink alcohol
- This activity will have a maximum of 26 travelers
Frequently Asked Questions (13)
Q: Can we bring our own bottle of wine?
Cancellation Policy
Still have questions?
We're here to help.
Activity code: C-277559
Traveler Photos
Reviews
Average 4.95 out of 5 stars based on 1,702 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 (13)
The answers provided below were previously given in response to questions from Cool Key West customers.
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Yes, you may! Please inform the check-in staff that you’ve brought your own. They will put it in a cooler and serve it to you.
Dec 2021Yes, there is. In 2017 the decision was made to disallow anyone 12 and under from Key West Wind & Wine Sunset Sail. The feedback on this move has been tremendously positive, as it is, after all, a wine tasting cruise.
Feb 2023The 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 activity start time.
- If you cancel less than 24 hours before the activity start time, the amount you paid will not be refunded.
- Any changes made less than 24 hours before the activity start time will not be accepted.
- Cut-off times are based on the activity local time (EDT).
- Yummy hors d’oeuvres, paired nicely to the wines, are served throughout.
- 8 premium wines, all poured generously.
- 5 imported and domestic beers.
- Cans of soda and bottled water.
- Gratuities.
This activity requires good weather. If it’s canceled due to poor weather, you’ll be offered a different date or a full refund.
Apr 2025The minimum age for this activity is 13 to attend 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 2025Detailed check-in instructions – including meeting point address, Google map, and parking information – for Key West Wind & Wine Sunset Sail 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
- Yummy hors d’oeuvres, paired nicely to the wines, are served throughout
- 8 premium wines, all poured generously
- 5 imported and domestic beers
- Cans of soda and bottled water
- Gratuities
Additional Info
- Confirmation is instant and will be received at time of booking
- What to bring: camera, comfortable shoes, sunglasses, sunscreen, and a smile!
- The minimum age for this activity is 13 to attend and 21 to drink alcohol
- This activity will have a maximum of 26 travelers
