Search for "Paris" or "Colosseum"
Book online or call: (888) 651-9785

Small-Group Key West Sunset Sail with Wine

Badge of ExcellenceKey West, United States
Likely to Sell Out

From $99.95

Select Date and Travelers

Reserve Now & Pay Later
Secure your spot while staying flexible
Free cancellation
Up to 24 hours in advance.
  • 2 hours (approx.)
  • Mobile ticket
  • Offered in: English
  • Good for avoiding crowds


Escape to the still waters off the coast of Key West on this small-group, sunset wine-tasting cruise. Enjoy the scenery and peaceful calm of a late afternoon sail on board a 65-foot schooner. Sample up to eight different wines and/or five different beers. Also included is a gourmet cheese buffet and other appetizers, like summer sausages, water crackers with brie, green apples with a honey drizzle and more. Then watch as the sun glistens and gently settles into the water, a perfect ending to a perfect cruise.
  • Enjoy a sunset cruise off the coast of Key West
  • Sample a variety of wine and beer
  • Snacks and beverages included
  • Small group ensures a personalized experience

What's Included

  • Unlimited beer, wine and soft drinks
  • Wine tasting
  • Light refreshments
  • Gratuities

Meeting And Pickup

Meeting point

  • 255 Front St
    255 Front St, Key West, FL 33040, USA

    Please arrive 30 minutes prior to your departure to check in. We are located at the base of the Opal Key Resort. Walk up the ramp between the Resort and the Art Museum and we will be the second shop on the left

End point

This activity ends back at the meeting point.

What To Expect

Additional Info

  • Confirmation will be received at time of booking
  • Minimum drinking age is 21 years
  • Not wheelchair accessible
  • Near public transportation
  • Must be 13 or older for this trip.
  • Most travelers can participate
  • This tour/activity will have a maximum of 26 travelers

Cancellation Policy

You can cancel up to 24 hours in advance of the experience for a full refund.

  • For a full refund, you must cancel at least 24 hours before the experience’s start time.
  • If you cancel less than 24 hours before the experience’s start time, the amount you paid will not be refunded.
  • Any changes made less than 24 hours before the experience’s start time will not be accepted.
  • Cut-off times are based on the experience’s local time.
  • This experience requires good weather. If it’s canceled due to poor weather, you’ll be offered a different date or a full refund.

about cancellations.

Frequently Asked Questions

The answers provided below are based on answers previously given by the tour provider to customers’ questions.

Q:What is the policy on sanitization during Small-Group Key West Sunset Sail with Wine?

A:The policies on sanitization are:
  • Regularly sanitized high-traffic areas
  • Gear/equipment sanitized between use
  • Transportation vehicles regularly sanitized

Traveler Photos

See more
631 reviews
Total review count and overall rating based on Viator and Tripadvisor reviews
Reviews by Viator travelers.
Showing 1-10 of 631 reviews
Donald_M, Aug 2022
Great Crew! Great time! Highly recommend, Great value, hors d’oeuvres were very good. Would definitely will come back
Crew was very friendly...
Jennifer_D, Aug 2022
Crew was very friendly and informative. Wine and snacks were great. Saw some dolphins. All in all a great experience.
Beautiful night on the water away from the crowds
Krista_T, Aug 2022
Beautiful sailing tour with a small group of people! Crew was awesome, wines were delightful and we will 100% do it again! Thanks!
Victoria_H, Jul 2022
Beautiful night on the water. Great crew on the boat. A must do in Key West. A night we will remember forever.
Don’t hesitate!
Kim_M, Jul 2022
The whole experience was great. It was a hot and humid day and this trip was a welcomed respite. It was very comfortable on the water. The crew was very personable and engaged. The wine and snacks exceeded expectations.
The staff was very...
Mark_B, Jul 2022
The staff was very welcoming and hospitable! And the cruiser was perfect. Best part of our trip. Would definitely recommend it to anyone down here for vacation
Stunning sunset sail
Lori_D, Jul 2022
Captain Mary and crew made this trip memorable and fun. The best sunset we saw on our week at Key West.
Fun night!
Amanda_S, Jul 2022
This sunset sail was fantastic! The weather was perfect and the crew was amazing! Bronza, Rose, and Dan made the experience very enjoyable for all. They came around several times with wine and appetizers. The small size of the group also made for a great experience. We got to meet some other couples and there was plenty of seating for everyone.
Wine and sunsets never get old.
dianefuchs, Jul 2022
This was the best sunset cruise we have ever taken. And we have taken many. We actually sailed most of the trip until it was time to motor to the dock. Would definitely do it again and highly recommend this trip for anyone.
Amazing sunset sail!
Jean_W, Jul 2022
What an amazing cruise! Great crew, unique and delicious appetizers and nice selection of wines! The crew took the time to get to know each guest and were always very attentive!
Captain Mary and her...
Shelley_H, Jul 2022
Captain Mary and her experienced crew provided impeccable wine service with a perfect selection of music to salute the end of a beautiful Key West!!
Sunset sailing!!!
Jimmy_V, Jul 2022
First time on a sail boat. Awesome experience! Crew and staff were great. I will book again on return visit.
Fun and memorable
Sanket_A, Jun 2022
Great fun crew. Good times and memorable. We Would do their half day trip if we had extra time. Appreciated the smaller passenger count as we watched other boats with standing room only.
Don’t Book With TripAdvisor, Call Operator Directly.
Craig_S, Jun 2022
No problem with operator, problem is with TripAdvisor. Sunset Sail was raining with choppy seas. We called the operator and they said I had to deal with TripAdvisor. I messaged TripAdvisor and they refused my refund of 234.00. Crazy! Who wants to do a sunset sail in rainy choppy seas. Don’t use TripAdvisor, book directly with merchants!!
Great captain and crew....
Cheryl_K, Jun 2022
Great captain and crew. Very accommodating to our group. Appreciated the extra touch iof music requests and proving us the coordinates for our memory of the sunset.
Great experience!
Suzanne_H, Jun 2022
It was a great experience! Very nice schooner. The wine tasting was a nice addition. Bronco, the captain, Dani and Logan, the crew were super nice, knowledgeable and very helpful. I would definitely sail with them again!
Sunset Cruise with the Best Crew
David_E, Jun 2022
Captain Mary and crew were amazing. They were very engaging and fun. I had the best sparkling wine I’ve ever tasted, the sunset was beautiful, and the crew really improved the experience. Would recommend to anyone visiting to check this out.
Spectacular and informative
Jean_S, Jun 2022
Just a wonderful experience with an incredible crew.. Great views, spectacular sunset and The Eagle too.
Great experience
Judy_C, Jun 2022
Megan was our captain and she was great as were the young men serving the wine and snacks. It was gorgeous night with a magnificent sunset. I would do it again in a heartbeat!
Perfect Sunset Cruise
Erika_H, Jun 2022
We had a great time on this tour! Bronza was our captain and did a great job, as well as as the rest of the crew. The wine and snacks were great. It was a beautiful evening and a greta sunset! I highly recommend this tour and the staff!!!


Product code: 7506P2