Key West, FL > Sunset Cruises
06/06/2020 ~ 06/12/2020

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

Duration: 2 Hrs.


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.


255 Front St, Key West, FL 33040, USA

Wind and Wine Sunset Sail

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Don't take our word for it

Verified Traveler Reviews

Sunset trip

about 3 months ago
It was great - the crew was excellent
Bobby E

Sunset cruise with no sunset

about 4 months ago
Great crew that took care of us! The sunset alluded is that evening but we saw a spectacular moonrise and watched a man propose to his girlfriend. Very impressed that crew member Joe had memorized everyone’s names in about 30 minutes. I would definitely recommend.
Randall B

Great Fun

about 8 months ago
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.
Rocky M


about 9 months ago
Great trip. Crew with Brianna was the best! Thanks!
Cydell J