Key West Wind & Wine Sunset Sail

1,391 Reviews 4.95 out of 5 stars Based on 1,391 traveler reviews collected by Key West Water Sports and TripAdvisor |
Badge of Excellence |Badge of Excellence This experience is highly rated by travelers and has met our top quality standards.
Key West

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This is usually booked 17 days in advance.

2 Hours (approx.)
Mobile Ticket
Instant Confirmation

Overview

The Wind & Wine Key West Sunset Sail has been honored with a #1 rating on Key West Water Sports three years running.

Highlights

  • Rated #1 on Key West Water Sports 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 Key West Water Sports for three consecutive years. 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.

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What's Included

  • Sunset Sail Aboard a Modern Style Schooner
  • Fancy Cheeses, Crackers and Fruit
  • Premium Wine
  • Gratuities
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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.

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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! 


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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.

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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.

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Additional Info

  • Confirmation is instant and will be received at time of booking
  • Not wheelchair accessible
  • Vessel has a toilet
  • Suitable for travelers of all fitness levels
  • What to bring: camera, comfortable shoes, sunglasses, sunscreen, and a smile!
  • The minimum age for this tour is 13 (it is a wine-tasting sunset sail, after all)

Frequently Asked Questions

(13)

Q: Can we bring our own bottle of wine?

A: Yes, please inform the staff upon check-in that you have brought your own bottle of wine. They will place it in a cooler, and a staff member will serve it to you. Sep 2022

Cancellation Policy

You can cancel up to 24 hours in advance of the tour for a full refund.

Still have questions?

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Activity code: C-277559

Traveler Photos

Reviews

4.95
1,391 reviews

Average 4.95 out of 5 stars based on 1,391 traveler reviews collected by Key West Water Sports and partner sites such as Cool Destinations and TripAdvisor

5 stars
1,334
4 stars
42
3 stars
15
2 stars
0
1 star
0

Loading Options
Don't miss out!
This is usually booked 17 days in advance.

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Cancellation Policy

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100% refund
No refund

You can cancel up to 24 hours in advance of the tour for a full refund.

  • For a full refund, you must cancel at least 24 hours before the tour’s start time.
  • If you cancel less than 24 hours before the tour’s start time, the amount you paid will not be refunded.
  • Any changes made less than 24 hours before the tour’s start time will not be accepted.
  • Cut-off times are based on the tour’s local time.
  • This tour requires good weather. If it’s canceled due to poor weather, you’ll be offered a different date or a full refund.

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