Key West Wind & Wine Sunset Sail

1,332 Reviews4.95 out of 5 stars Based on 1,332 traveler reviews collected by Inside Key West 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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2 Hours (approx.)
Mobile Ticket
Instant Confirmation

Overview

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

Highlights

  • Rated #1 on Inside 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 Inside Key West 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
  • Near paid parking
  • Suitable for travelers of all fitness levels
  • Not wheelchair accessible
  • 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

The answers provided below are based on answers previously given to travelers by the Inside Key West customer support team.

What food and drink is served on Wind & Wine?

Choose from up to 8 different types of wine from around the world (taste through them all, or just choose your favorites).

Choose from 5 different types of imported and domestic beer.

Enjoy a wonderful variety of delicious appetizers like Havarti Dill, Smoked Gouda and Summer Sausage, Caprese Skewers, Water Crackers with Brie, Green Apple with a Honey Drizzle, and more.

Is there an age limit for the Wind & Wine Key West Sunset Sail?

Yes, 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.

What is the weather cancellation policy?

If the Key West Wind & Wine Sunset Sail must be canceled due to bad weather, and you cannot go on another day or time, you will be issued a refund by Inside Key West.

Where can I park my car?

If required, parking instructions for the Key West Wind & Wine Sunset Sail will be included in your confirmation email.

Where is the meeting point for this activity?

Detailed 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 Inside 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!

Cancellation Policy

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

Still have questions?

We’re here to help.
Live Chat, Text, Call, or Email our friendly customer support with your questions.

Activity code: C-277559

Reviews

4.95
1,332 reviews

Average 4.95 out of 5 stars based on 1,331 traveler reviews collected by Inside Key West and partner sites such as Cool Destinations and TripAdvisor

5 stars
1,274
4 stars
42
3 stars
15
2 stars
0
1 star
0

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