We had an amazing experience with Captain Chase and First Mate Jamie. They were very informative as to the area, local wildlife and, since it was our first sailing adventure, the boat and how it all works. Highly recommend this activity!!
About Activity
What's Included
Includes
- Bottled water
- Private charter
- Captain and mate
- Soft drinks
Excludes
- Gratuities
- Alcoholic drinks (available to bring)
- Hotel pickup and drop-off
Departure & Return
Departure Point
- 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.
Return
- 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.
Itinerary
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!
Language Offered
Additional Info
Cancellation Policy
Reviews
A beautiful afternoon on the water with fresh winds and good stories. Will and Cass made the most of our excursion down Fleming, around Sunset Key, and along the waterfront. Hang on to the dog, rails in the water!
We took the private day sail on december 22, 2025 age range from 15 to 72 a family of 5. Will and Cameron were the best crew we could of possible had. The day was windier than normal so turned out to be excellent day for sailboating. They were very knowledgable and also alot of laughs. This is agreat opportunity for all age groups . Would definately recommend to anyone coming to Key West . This was on our bucket list and would definately do again with this crew if come back to key . Tell the boys if they ever come to Indiana to look us up.
We had a great time on a private sail. Captain Harley was a great sailor, very friendly and informative. His first mate engaged in conversation and kept us entertained. HIGHLY RECOMMENDED
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.
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’.
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!!
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 🥂
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!
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!!
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!!
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!
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 😎👍
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.
We went out on the High Tide a week ago. Our captain was Mark. He was great! We enjoyed sailing around and then we stopped for a dip in the water. He provided the drinks and some snacks! It was a great time - enjoyed talking to the crew and hearing all of their stories. It was nice to get away from the hustle of downtown and actually enjoy the area from a different perspective. Thanks Captain Mark!
Captain Eric and first mate Shaun took us out on an amazing sailing experience!! I had never sailed before and now I wish I had tried it sooner! Beautiful scenery and amazing crew! Would definitely sail with them again. And little Lalana was an awesome addition to the crew
On a tight floridian trip - The High Tide & her crew, captain Kelsey and mate Sean created a moment on the sea with the wind on starboard we all cherished as a starmoment of Christmas 2018.. We give them our best recommendation.. Nicolai, Nikolai, Lene & Henrik..
We sailed on Dec 17, 2017. We booked the 90 minute private sailing on the High Tide. I received a call the day before to say that our boat was still in dry dock overall, and they offered us to sail on a larger boat for the same price. They picked us up, brought us to our boat and we left on time. The sailing weather was perfect, and the crew was friendly and accommodating. There were cold drinks in the cooler. We, 11 yr old son, husband and myself really enjoyed ourselves together on this excursion.
This is our third year of doing the Starlight Sail on the High Tide. It continues to be the highlight of our trip! Sean and Kelsey were amazing hosts and we truly had a great time! If you have never experienced this, you do not know what you are missing! Thanks again for the amazing night among the stars.
We had a fabulous time on our 90 minute sailing excursion around the keys in October 2017. The crew was super flexible and responsive and helped us reschedule our sail due to weather. We had a beautiful day and loved it! Crew is friendly and fun. I would definitely recommend doing this while in the keys. Unbelievable views!
Monday through Friday 9 am to 7 pm EST
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