Sunset Sailing: Wine Tasting on Stock Island

91 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 be sailing and enjoying an assortment of hors’devours while the sunsets in the distance. There will be a variety of wines, beers and non-alcohol beverages available.

What's Included

Carbonated beverages
Bottled water
Snacks
Up to 18 years old

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

(91 Ratings)

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1 star

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

Nicole

Oct 20, 2025

Sunset Cruise Did Not Disappoint - Had the best time in Key West for my husband’s 50th birthday. The sunset cruise was definitely a highlight! The crew were very professional, entertaining and accommodating. Highly recommend!

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P8557oqmiker

Oct 19, 2025

Sunset - Very relaxing and enjoyable! Had a great time. Would definitely recommend it as an alternative to the large catamaran sails.

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Katie

Oct 11, 2025

My happy place sun set and wine!!! - Lovely beautiful sunset cruise. The wine and food pairings with it were wonderful!! I felt very safe on this trip. Staff were all professional and informative. I can’t wait to return one day hopefully next year!!!

Review provided by Tripadvisor

Wmason43

Oct 5, 2025

Sunset sail, wine and snacks - Wonderful way to see a sunset. We enjoyed our sail and the wine and snacks were excellent. Luke, the captain, along with Conner and James made the sail exceptional. We took our moms on the cruise that we did four years ago and had a fabulous time. Our moms loved it. We love it. I will do it anytime I’m in Key West. I have enjoyed this both times and will definitely come back. I would recommend them to anyone. You’ll see some amazing views and potentially see some dolphins. I want to do it again. If I wasn’t leaving tomorrow, I would.

Review provided by Tripadvisor

Sandeel2016

Sep 30, 2025

Wonderful experience! - Wonderful crew, great wine tasting of 4 reds and whites with matching charcuterie and n a beautiful sailboat with a spectacular sunset. Who could want more?

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Adam_d

Aug 2, 2025

Great experience and great views! - This was an awesome experience. The food and wine selection was great! Staff was awesome! And the views of the sunset were top notch! Would highly recommend!

Review provided by Viator

Cliffordc_12

Jul 29, 2025

Rainbows after the storm - Waited out lightning & thunderstorms, but all was worth the wait. Sunset was beautiful & crew was awesome! Wine & apps were plentiful & met great people.

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Jason_d

Jul 24, 2025

Awesome sunset sailing experience - Sunset sail was absolutely amazing. The atmosphere was laid back and peaceful with top-notch hospitality. The Captain and first mate Lexi were exceptional. Definitely would sail again on this particular tour package and very interested in checking out other trip and tour offerings by Danger.

Review provided by Viator

249michelen

Jul 18, 2025

Intimate Wine and Sunset Sail - We have taken many cruises on Danger from downtown Key West. This was our first from Stock Island. It was wonderful, less crowded, more intimate and able to really get to know the Captain and Ship Mate. It was also our sister’s first time and she loved it. It felt more like a private charter. Highly recommend!

Review provided by Tripadvisor

Check Availability

From $115

up to 15 guests

1 - Adult