Key West Private Harbor Sailing Charter

Experience luxury with this private day sail charter in Key West. Embark on an immersive 90-minute journey around the Florida Keys while enjoying serene water views of the city. If luck is on your side, you might also spot some playful dolphins near the bow!

Duration: 1 hour, 30 minutes
Cancellation: 24 hours
Highlights
  • Sunset Sail Key West - Our Captain and mate will greet you at the boat. You’re welcome to board 15 minutes before departure. Soft drinks and water are included and you are welcome to bring your own adult beverages and snacks. We have ample ice and cooler space. To find the boat: Go to 202 William St. Key West, FL. Walk down the dock in front of the Schooner Wharf Bar and look for our sign in front of the first floating dock. Walk down that floating dock and you will see the pretty green sailboat name HIGH TIDE.
    Welcome Aboard!
    If you would like to add more time or a swim to your sail, please make sure to call ahead to ensure that we can accommodate!
    Sit back and relax and enjoy the sail or ask the Captain to let you take a turn at the wheel and become a sailor!
What's Included
  • Bottled water provided
  • Exclusive private charter
  • Expert captain and mate on board
  • Complimentary soft drinks
What's Not Included
  • Gratuities
  • Alcoholic drinks (available to bring)
  • Hotel pickup and drop-off
Additional Information
  • Children must be accompanied by an adult
  • Minimum drinking age is 21 years
  • Pricing is per boat/charter
  • Maximum on the boat is six (6) people
Location
Sunset Sail Key West
William Street
Come down the dock in front of the Schooner Wharf Bar. Look for our company sign - Sunset Sail Key West. Walk down that floating dock you will see the pretty green sailboat named HIGH TIDE. If you have any difficulties finding the vessel, please don't hesitate to give us a call at 305-587-4488.
Cancellation Policy

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

Customer Ratings
4.9
(15 Ratings)
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1 star
Joshua_b
Sep 4, 2024
Awesome time! - Great time and awesome crew! We were able to drop off wine and snacks and they put in the cooler for us. Enjoyed chatting with them. Boat was great.
Review provided by Viator
Lindabeckenham
Aug 1, 2024
A great time out on the waters - Had a wonderful time sailing out on High Tide with Harley and Kasey who were very knowledgable and full of interesting stories. Our teenage daughter was not enjoying the sailing experience and obviously prefers the more thrilling speed where there is less ‘tilt’ but nonetheless it was one of our best experiences and we were so lucky as the thunderstorm hit 20mins after we stepped back on shore. It was meant to be!!
Review provided by Tripadvisor
Navigate10347026640
Jan 27, 2024
7 star experience compared to other adventure companies in keywest . - From booking staff Austin at duval to check in guy Marshall and jet ski crew Stefanie ( 7 star) Ben every sunset adventures keywest staff is friendly and humorous. They are real assets. I am a local keywest residence.. they treated all tourists and local the same. Great experience with this company compared to other local tour / adventure companies . I will give 7 star to staff and management also company. My 11 year old son enjoyed . He can’t wait to be 16 to ride jet ski by himself . Cheers 🥂
Review provided by Tripadvisor
Rainwater9
Aug 28, 2023
Great sunset sailboat cruise in Key West! - We had an outstanding time and experience. Jade and Tabitha did a great job piloting the sailboat and hosting our group. Look forward to a repeat trip next year!
Review provided by Tripadvisor
Freds_trips
Apr 5, 2021
Awesome Adventure! - Awesome first time sailing experience. The crew was great - very friendly, knowledgable and experienced! Even thought the winds were high, the ride as smooth! Would highly recommend!!
Review provided by Tripadvisor
Wendi
Aug 15, 2020
Awesome!! - The boat was a little hard to find, but that's my only complaint. The boat, our captain and crew and the tour were all incredible!! Our Captain had just returned from maternity leave and was so fun, personable and knowledgeable. Our First Mate was awesome, too! We will definitely book this tour the next time we're in key West! Thank you!!
Review provided by Tripadvisor
Lria
Mar 8, 2020
Amazing Incredible Outstanding - This was my first time in a sailboat and it was AMAZING!!! Spent this experience with my husband and kids! Libby and Harley made my 50th birthday INCREDIBLE!! They are knowledgeable, helpful, fun, and just the absolute best!!!! Thank you so much! We will see you again!
Review provided by Tripadvisor
Excursion201122
Feb 1, 2019
Wonderful day on the water - We had a wonderful afternoon on the High Tide!! The crew was awesome, with warm weather you can only get in Key West in January. I would highly recommend this cruise to everyone 😎👍
Review provided by Tripadvisor
Jaxhopper
Jul 12, 2018
GREAT Time on this Sailing Charter - Do not hesitiate to charter the High Tide. The four of us had an awesome afternoon. The sky was blue, the sun was shining, the winds were blowing and the sea was calm, but most importantly was the skill and friendliness of Captain John. Just loved the sail and can't wait to come back.
Review provided by Tripadvisor
Linda_s
Aug 7, 2024
Trip was excellent; waste of time going through Viator. - Had a wonderful time sailing out on High Tide with Harley and Kasey who were very knowledgable and full of interesting stories. Our teenage daughter was not enjoying the sailing experience and obviously prefers the more thrilling speed where there is less ‘tilt’ but nonetheless it was one of our best experiences and we were so lucky as the thunderstorm hit 20mins after we stepped back on shore. It was meant to be!! The ooor experience was relating to aviator themselves as I contacted them the day before to try and get an earlier time sailing due to impending storms and the lady said she could not do anything for same day trips (!!!! It was not same day))) and when I said it was next day she said she still couldn’t do anything, dismissed us and gave us the direct company phone number which we couldn’t call as we have UK phones and would cost too much. Complete waste of time going through an ‘agent’. Will book direct next time. The hotel concierge we were staying at was way more helpful for us, coming up with suggestions and being ‘helpful’.
Review provided by Viator
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