Sunset Sailing: Wine Tasting on Stock Island

101 Ratings

Monroe County

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Sail into the sunset on a 65-foot schooner, savor global wines, premium beers, and gourmet appetizers. Perfect for intimate gatherings.

Duration: 2 hours

Cancellation: 24 hours

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Highlights

Coconut Row - Guests will embark on a delightful sailing experience, savoring a selection of hors d’oeuvres as the sun sets on the horizon. A variety of wines, beers, and non-alcoholic beverages will be available for enjoyment.

What's Included

Snacks
Carbonated beverages
Bottled water
Alcoholic beverages

Additional Information

Board our 65 foot schooner for an intimate voyage with a select group of travelers. Savour internationally sourced wines, along with a choice of IPA, foreign or local beers. Relish a range of appetizers. Soak in a breathtaking sunset on the sea. Our offerings include 8 types of Wine - 4 Red, 3 White & a Champagnoise. Enjoy 5 Premium Beers - Imported &…

Location

Coconut Row

Check-in time for your excursion is 30 minutes prior to departure. Go down Shrimp Road, Turn into last parking lot at Perry Hotel and Marina, go down to the end of J dock, slip 5.

Cancellation Policy

For a full refund, cancel at least 24 hours before the scheduled departure time.

Customer Ratings

5.0

(101 Ratings)

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368ak

Apr 7, 2026

Sunset cruise - We had a great evening. The ship was clean and organized. There was enough seating for everyone. The staff was very friendly and accommodating. The wines were diverse enough to please everyone, it seemed. The appetizers were plentiful, well put together and tasty.

Review provided by Tripadvisor

Ny31fordor

Apr 6, 2026

Great way to spend evening! - Great time, crew very attentive and informative about wines being served.

Review provided by Tripadvisor

Jeaniem274

Apr 1, 2026

Spectacular Sunset Views - A fabulous experience- the captain and staff were friendly, efficient and very accommodating. Spectacular sunset views - an evening to remember!

Review provided by Tripadvisor

Hendersontrking

Mar 30, 2026

Fabulous Sunset Cruise! - Fabulous sunset cruise. Great staff on board, lots of vino, good snacks!

Review provided by Tripadvisor

Robert

Mar 28, 2026

Beautiful Sunset Sailing - Captain was excellent and crew was friendly and helpful. We sat in the back next to the captain affording us the benefit of his commentary. Nice wines and snacks. At sunset the captain steered us into an unobstructed view of a perfect sunset. A beautiful evening.

Review provided by Tripadvisor

Erieshores8

Mar 4, 2026

Another Great Evening with Danger Charters - We went out in The Sarah for the wine & sunset cruise. We have been out with Danger many times over the years and have always had a 5 star experience. Capt Mary and our crew members Anna and Morgan were amazing! We brought along friends for their 1st trip with Danger and they were blown away by a great evening of sailing. I highly recommend and ask for our crew they are the best!!!

Review provided by Tripadvisor

C5936avgregf

Feb 12, 2026

Two Hours of Bliss in the waters of Key West - This was, once again, a superb experience! The boat is comfortable and spacious, the crew and captain were all terrific! Lauren, who led the tasting was great - a lovely selection of wines - Prosecco, Albarino, French Chardonnay (my favorite), an Oregon Pinot Noir (delicious), an Australian Cabernet Sauvignon, and more! Excellent variety. The appetizers served were very tasty. We took my sister and brother-in-law for their first time - they loved it. We were all sad to be pulling back in to the dock! It's a great experience and we highly recommend it! Being on the water is a constant pleasure!

Review provided by Tripadvisor

Travellight007

Jan 20, 2026

The crew was personable and accommodating. The food and wine were explained and delicious. The craft was beautiful. The sunset w - Oops I wrote my review as the title. This was a super fantastic trip with a superb crew and delicious food and drink. I would definitely do it again.

Review provided by Tripadvisor

Larissa_v

Jan 12, 2026

Excellent! - We had a wonderful time on the Wind and Wine Sail! It was great meeting new people while enjoying delicious wine and tasty hors d’oeuvres. One of the highlights was seeing baby dolphins jumping out of the water—such a special surprise. The sunset was absolutely stunning, and the crew was incredibly attentive and knowledgeable throughout the trip. I would highly recommend this experience!

Review provided by Viator

Tcklassen

Oct 30, 2025

Sunsets, wine, and dolphins... - The Wind and Wine Sail from Stock Island with Danger is a real gem! The beautiful sailboat is not crowded, the area in which we sailed just included us and not other sailboats vying for the sunset, the captains and mates (we went on 2 trips!) were excellent, and the bonus was a visit by some dolphins on both trips. The mate serves a great selection of bubbles, whites, and reds, as well as tasty hors d'oeuvres. The evening was peaceful, the music was soft and low, and the atmosphere was perfect. Our party of 4 highly recommends this fabulous way to view a Key West sunset.

Review provided by Tripadvisor

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