Key West Wind & Wine Private Charter (up to 30 guests)

1,690 Reviews 4.95 out of 5 stars Based on 1,690 traveler reviews collected by Key West Water Sports and TripAdvisor | Recommended by 99% of reviewers | Key West

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On average, this is booked 66 (55.20) days in advance.

2 hours (approx.)
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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.

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What's Included

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

    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.

    Read 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.

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    Show 2 more

    Sample Menu

    HORS D'OEUVRES Example items

    • Smoked Gouda cheese with summer sausage
    • Caprese skewers
    • Water crackers with Brie
    • Honey-drizzled green apple
    • Crudités
    • Fresh Fruit
    • Chocolate

    WINE Generously poured by crew

    • Four Reds
    • Three Whites
    • A Champenoise

    BEER Selection of five

    • Imported beer
    • Premium lager
    • Domestic beer

    NON-ALCOHOLIC Ice cold

    • Canned soda
    • Bottled water

    •—•

    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, and if you bring your own favorite bottle of wine, the crew will be happy to open and serve it to you.

    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?

    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

    Cancellation Policy

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

    Still have questions?

    We're here to help.
    Activity code: C-757

    Traveler Photos

    Reviews

    4.95
    1,690 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

    5 stars
    1,620
    4 stars
    51
    3 stars
    19
    2 stars
    0
    1 star
    0

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    Don't miss out!
    On average, this is booked 66 (55.20) days in advance.

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    What's Included

    Activity name

    • 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

    Activity name

    • 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

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    Free Cancellation

    100% refund
    No refund

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

    • 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).

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