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Wind & Wine Sunset Sail

4 Reviews
5.00 out of 5

$75 YouTube Video

Wind & Wine Sunset Sail

4 Reviews
5.00 out of 5

$75 YouTube Video

Top-rated Wind & Wine Sunset Sail is an unforgettable sunset experience—sailing on the warm tropical Caribbean waters of Key West.

  • #1 rating on for three consecutive years
  • Exclusive intimate Trip with just over twenty passengers aboard a beautiful sailing boat
  • Exceptionally Attentive and Accommodating Crew & Captain

Times Available: Daily / Duration: 2.5 Hours

Product Description

The Wind & Wine Sunset Sail is an incomparable sunset experience amid the warm tropical caribbean waters of Key West.

Rated among other Top Sunset Cruises in North America by Coastal Living Magazine, the unmatchable Wind and Wine Sunset Cruise is for people who want an upscale, yet casual sunset sail.

Departing nightly, we serve a selection of eight different wines from across the globe, to include four red, three white, and a Champagne selection, which makes wine aficionados love this excursion. It is virtually the only sailing excursion in the U.S. that serves “actual” wine. But for others, we provide an array of quality beer.

Hors d’oeuvres are also offered, making the evening a great start to enjoying Key West nightlife!

Additional Information


Romance, Special Occasions

Time of Day



2 hours




Complimentary fancy cheeses and crackers, fruit, imported and domestic beer, premium wines, sodas and bottled water.

Where is the departure point for this tour?
Detailed check-in instructions will be included in your confirmation email.

When do I need to arrive for check-in?
Please arrive for check-in 30 minutes before the tour begins. The exact tour start time may be based on your chosen options and will be noted on the confirmation you receive after booking.

Where can I park?
Parking is available on the 400 block of Caroline Street (it is a pay lot).

Do you provide a shuttle to the tour?
Currently, we do not provide transportation to the tour.

Can you pick us up from the airport?
Currently, we do not provide transportation from the airport.

More questions?
Please read the Inside Key West FAQs, or call +1 (866) 259-1333 for assistance with online booking.

4 reviews5.00 reviews for Wind & Wine Sunset Sail

  1. 5 out of 5


    When I first heard of the wind and wine sail, I first thought that this was another one of those tourist traps. But after going through the brochure and talking to my husband about it, we decided that it would actually provide a very good experience.

    The trip made me feel very special. Everything was carefully organized, the boat had a lot of space, and everyone was so nice to each other. The crew have also been friendly which helped make the atmosphere the best it can be.

  2. 5 out of 5


    At first, I wasn’t sure whether to join this sunset sail but my daughter convinced me to go. The truth was, I only went because I didn’t want her to go alone. It seems to me that a wind and wine sail would be the type of thing that only couples go to. Upon setting foot on the sailing boat though, I was suddenly glad I decided to join in.

    The staff was attentive to my every need so my trip felt special. The wines they served came from all over the world. If I remember correctly, it was three white wines, four red wines, and champagne. But what I enjoyed the most was seeing the Key West sunset views. It is now etched in my mind. The wine only came secondary to the experience. This is a trip a would recommend to anyone – whether you’re going with your daughter, son, or best friend – it’s a sailing experience you’ll enjoy.

  3. 5 out of 5


    If you’re looking for something that would spice up your relationship, I think that the Wind and Wine Sunset Sail would do the trick for you. My husband and I had an amazing time during the trip. I also like the fact that the weather is warm and night. It created an intimate atmosphere especially as the boat glided through the waters.

    Some people might be curious about the wine. Well, I’m not a wine connoisseur but the wine they offered during the trip tasted fine to me. They served white wines, red wines, and a type of Champagne. It all felt very sophisticated. Overall, the sail was relaxing and there was no stress at all. I enjoyed it thoroughly.

  4. 5 out of 5


    I’ve been to many sunset cruises but this one really tops them all! My wife and I had an amazing time on the Wind & Wine sail. It reminded me of a time when I was younger and more carefree. This really brings back all the good memories.

    The calm water, the stunning scenery, and the attentiveness of the crew are all very commendable. I’d definitely say go for it if you want to experience a romantic sunset sail here at Key West.

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