We noticed that you're using an unsupported browser. The Tripadvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.
About Sail Montauk
Step off the dock and onto one of our private sailboats for an exhilarating sail on the waters of Montauk. Take the tiller or just sit back and relax; we'll make your sailing experience one of a kind. Get a Taste of Sailing with our private 2 hour sails, or spend some more time on the water with a Sail & Swim package. Book a Private Lessons will help you fine tune your skills. If you're just looking to relax, come aboard for a private Sunset Sail with the best views in Montauk, perfect for sweethearts and groups of friends. No matter what your level of experience, create ever lasting memories when you Sail Montauk.
Read more
Closed Now
Hours Today: 8:00 AM - 8:00 PM
See all hours

Sail Montauk
Booking unavailable on Tripadvisor

Want other options you can book now?
180Reviews4Q&A
Traveler rating
  • 176
  • 2
  • 2
  • 0
  • 0
Traveler type
Time of year
Language
Selected filters
  • Filter
  • English
Megan H wrote a review Jun 11
3 contributions1 helpful vote
Review of: Taste of Sailing
My best friends surprised me with a sunset sail for a graduation gift. We sailed with Darius who was extremely fun, professional, and accommodating. Though the weather was not ideal, we had a wonderful time seeing Montauk from the water and got some great photos while we were at it. I will 100% sail with them again when I am back in Montauk!
Read more
Date of experience: June 2021
Helpful
Share
Tara P wrote a review Jun 9
12 contributions2 helpful votes
Review of: Taste of Sailing
We stayed at Guerney's Marina and we scheduled sailing for a Sunday afternoon. it was such a beautiful day out on the water. I would highly recommend this activity to anyone staying in Montauk for the weekend. The instructor was friendly and showed us how to sail! a must do!
Read more
Date of experience: May 2021
Helpful
Share
Sidney L wrote a review Jun 8
4 contributions
Review of: Taste of Sailing
My boyfriend and I had an amazing experience sailing! We were enjoying this activity for my birthday and it definitely was an unforgettable experience for the both of us. I will definitely be returning to sail again throughout the summer. Would highly recommend this activity.
Read more
Date of experience: June 2021
Helpful
Share
Haley C wrote a review Jun 8
3 contributions
Review of: Taste of Sailing
We booked a sunset cruise with Sail Montauk this past weekend and had the best time! Darius explained that he was happy to give us as much hands on sailing experience as we wanted but we were also free to just drink wine and enjoy the views. Unfortunately the weather didn’t cooperate so we, but Darius offered us the option for a 50% refund off if we wanted to go in early since the weather was bad. He was friendly and professional and told us stories about Montauk and the surrounding area. Could not recommend more!
Read more
Date of experience: June 2021
Helpful
Share
Radwa A wrote a review Jun 1
1 contribution
Review of: Taste of Sailing
this was an amazing experience for my first sailing lesson! with no background at all, Darius, the instructor and owner, did a great job of explaining everything & teaching me about sailing and how a boat works. it was a lot of fun and he was nice enough to refund me $100 because it wasn't windy enough to sail that day, however we stayed on the boat for the full 3 hours to enjoy the water and the sun. would 100% recommend and go back!! :)
Read more
Date of experience: May 2021
Helpful
Share
Previous
123456