Wind and Wine Sunset Sail

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Sail into the Key West sunset while sampling 8 fine wines from around the world, beer, and delicious hors d'oeuvres. Rated one of the top two sunset tours in North America by Coastal Living Magazine, this intimate and luxurious 2-hour sunset sail on a historic Schooner won't disappoint. Make new friends, enjoy tropical music, and delight your palate as you watch the sun melt into the water.

Activity Highlights

  • Relaxing sunset sail with wine, beer, and appetizers
  • Sample 8 carefully selected wines and 5 beers from around the world
  • One of the only sailing excursion in the US to serve "real wine"
  • Take in the sights and sounds of Key West at dusk with fellow wine enthusiasts


Appetizers such as (Varies):

  • Havarti Dill.
  • Smoked Gouda.
  • Green Apple with drizzled honey.
  • Summer Sausage.
  • Caprese Skewers.
  • Water Crackers with Brie.

What's Included

  • Wine offerings typically include 4 reds, 3 whites, and one Champagne or sparkling wine (produced via the Méthode Champenoise)
  • 5 types of beer (imported and domestic)
  • Appetizers
  • Water and sparking water
  • Pepsi, Diet Pepsi, and Gingerale

What to bring

  • Hat
  • Camera
  • Sunglasses
  • Weather appropriate clothing
  • Cash or credit card for gratuities


  • Must be 21 or older to consume alcohol.
  • No customer under age 13 permitted.
  • Maximum of 25 guests.
  • Not handicap accessible.
  • No service animals.

Additional information

  • Parking is available on-site for a fee.
  • Gratuity is not included.
  • For parties of 5 or more, a gratuity of 15% will be collected upon arrival.
  • Must arrive 30 minutes prior to departure.
  • Restrooms available on board.

Cancellation policy

Customers with parties of four or less must cancel at least 24 hours prior to their arrival date and time to receive a full refund minus a $5 service fee. Customers with parties of five or more must cancel at least 72 hours prior to their arrival date and time to receive a full refund minus a $5 service fee. Customers canceling after the stated period will not be eligible for a refund. If the vendor deems the weather unfavorable the experience may be rescheduled for a later time/date or a full refund will be issued. No-shows will not be refunded. Customers may make changes to the reservation without any fees as long as it's requested 72 hours before departure.

Check Availability/Book online

Read what other TripShock! travelers think about the Wind and Wine Sunset Sail. What they loved, what they liked and what they think could be improved, it's all here to help you make the most of your next trip. Only TripShock! customers may leave reviews. Please login to your reservation to post your review.

1-10 of 16
  • Kristina pohl USA about 13 days ago


    Verified TripShock! Traveler Review
  • Laura Schneider Alabama, USA about 2 months ago


    Verified TripShock! Traveler Review
  • Rocky Moreno USA about 4 months ago

    Great Fun

    All female crew and they rocked it. The wines were good. The crew didn't make us adhere to a strict tasting (i.e. they let us skip around the sampling and have refills on the wines we liked). All three of the crew members were accommodating, friendly, and fun. The food was good. The sunset ending up being blocked by clouds, but the crew worked hard to get to the best vantage point. All in all it was a great trip. We look forward to doing it again.

    Verified TripShock! Traveler Review
  • Cydell Jarquin USA about 4 months ago


    Great trip. Crew with Brianna was the best! Thanks!

    Verified TripShock! Traveler Review
  • Dean Hemohill USA about 4 months ago

    Beautiful sunset

    Nice selection of wine, need more sweet selection. Crew was great, boat was in nice shape, hors d’ouvers were tasty!

    Verified TripShock! Traveler Review
  • Richard Jones USA about 4 months ago

    Crew was professional and fun.

    Super time. Good wine. Well done.

    Verified TripShock! Traveler Review
  • George Hoverkamp USA about 5 months ago


    Great time. Appetizers were great. Crew was fantastic.

    Verified TripShock! Traveler Review
  • Fran Plumley USA about 5 months ago

    Sunset sail

    Very personable and knowledgeable. The crew were excellent.

    Verified TripShock! Traveler Review
  • Ethan Uguccioni USA about 6 months ago

    Great sunset cruise

    Great cruise. Crew was wonderful and entertaining. Well worth the cost. Beautiful boat.

    Verified TripShock! Traveler Review
  • United States about 8 months ago

    perfect evening

    We took the Wind and Wine Sunset Cruise and it was absolutely our most perfect evening in Key West. Check in was very easy, the cruise itself was calm and we enjoyed the food and wine, and there were no bad seats. This cruise should not be confused with a dinner cruise as the food is very light, yet very good. The wine tastings were great and they made sure there was plenty for all. Having taken the cruise, I would do it again—it was just that good.

    Verified TripShock! Traveler Review
1-10 of 16
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