(855) 274-1023 Key West Questions? Call Us Now!

Key West Wind & Wine Private Charter

140 Reviews | Key West

Loading Options

2.5 Hours (approx.)
Likely To Sell Out
Mobile Ticket


Keeping you safe during COVID-19
What you can expect during your visit
Face masks required for guides in public areas
Face masks required for travelers in public areas
Hand sanitizer available to travelers and staff
Regular temperature checks for staff
Regularly sanitized high-traffic areas
Social distancing enforced throughout the experience
All boats regularly sanitized

The Wind & Wine Key West Sunset Sail has been honored with a #1 rating on Trip Advisor three years running. See the sunset on a beautiful 65ft sailing boat.


  • Rated #1 on Trip Advisor for three years running Beautiful sailing boat
  • Exclusive Trip with just over twenty passengers
  • Amazing Key West sunset views
  • Attentive and Friendly Crew



What's Included

What To Bring

Additional Info

Frequently Asked QuestionsFAQ



Average 4.89 out of 5 stars based on 140 verified reviews from Tours of Key West and TripAdvisor

5 stars
4 stars
3 stars
2 stars
1 star
Key West Wind & Wine Private Charter
donp441, Jan 2022 Verified
Great evening on the water! Sampled 8 different wines plus appetizers. Would definitely recommend. Staff were friendly and very capable.
Key West Wind & Wine Private Charter
Chris_M, Dec 2021 Verified
Megan, Nicole and Ellen were all fabulous, Great service and attention and really made the trip fun. Fun engaging personalities. Girl power!
Key West Wind & Wine Private Charter
Robin_M, Dec 2021 Verified
Fantastic and very professional crew. Great time! We will book again with Danger charter group for sure.
Key West Wind & Wine Private Charter
daleokid, Dec 2021 Verified
Danger Charters was recommended to us and they didn't disappoint. Great crew, excellent choice of wine, relaxing environment. Highly recommend them.
Key West Wind & Wine Private Charter
MateuszDziubek, Dec 2021 Verified
Amazing trip and an amazing proposal! Thank you so much!!! We loved it!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!! The crew was very helpful with my surprise by taking pictures.
Key West Wind & Wine Private Charter
stephen h, Dec 2021 Verified
Great evening, great hosts. Our ship, trip and view was excellent! Our hosts were even better...would go again next time visiting
Key West Wind & Wine Private Charter
85lubak, Dec 2021 Verified
Great evening, all of us enjoyed. The crew, captain Bronza and Rose, were wonderful, really made the trip special. More interesting than your standard sunset cruise!
Key West Wind & Wine Private Charter
jeffdR5699NN, Dec 2021 Verified
Anna was knowledgeable on wine and sailing. Very engaging with everyone and had info to share re Key West. Good wine and food pairings. Good times thanks
Key West Wind & Wine Private Charter
Asvgiridhar, Dec 2021 Verified
Captain bronza and other crew members were really good.it was an amazing experience for sunset I will definitely recommend for everyone
Key West Wind & Wine Private Charter
ishkbibel, Dec 2021 Verified
We have done the sunset cruise a number of times and always a memorable experience. The sailboat, wine and food, and crews are all fantastic, plenty of drink options and your glass is never empty along with a nice selection of appetizers too. This year we joined the all Girl crew and they are first class, Captain Mary, Rose and Ann made our trip super special with wonderful conversations and fun sailing on a beautiful sunset evening. A Big Thank You to the crew and the office help as well on our arrangements. Will be back next year!

Still have questions?

We’re here to help. Call (855) 274-1023 to speak with a Destination Specialist
Product code: C-757

Similar Tours & Activities

Beach Day With Picnic Lunch

 3 to 5 hours  Hotel pickup offered  Instant Confirmation

Champagne Celebration Sunset Cruise

 2 hours  Instant Confirmation

Key West Sunset Dinner Cruise

 2 hours  Instant Confirmation

Customers Who Bought This Tour Also Bought

Badge of Excellence Badge of Excellence This experience is highly rated by travelers and has met our top quality standards.

Key West Split Fishing Charter

 4, 6 or 8 Hours

Key West Light Tackle Fishing Charter

 4, 6 or 8 Hours  Instant Confirmation
Best Rate

Key West PADI Open Water Certification

 3 Days
Best Rate