Sail Montauk
Sail Montauk
5
8:00 AM - 8:00 PM
Monday
8:00 AM - 8:00 PM
Tuesday
8:00 AM - 8:00 PM
Wednesday
8:00 AM - 8:00 PM
Thursday
8:00 AM - 8:00 PM
Friday
8:00 AM - 8:00 PM
Saturday
8:00 AM - 8:00 PM
Sunday
8:00 AM - 7:00 PM
Full view
About
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.
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Most Recent: Reviews ordered by most recent publish date in descending order.
Detailed Reviews: Reviews ordered by recency and descriptiveness of user-identified themes such as wait time, length of visit, general tips, and location information.
5.0
254 reviews
Excellent
250
Very good
2
Average
2
Poor
0
Terrible
0
Melissa C
1 contribution
Aug 2024 • Friends
This is a fantastic company to go sailing with out of Montauk NY. They are very responsive when making reservations and make every effort to accommodate your needs. The captains are all certified and top notch and are socially sensitive to whomever is onboard.
Written August 29, 2024
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
AndrewModelski
New York1 contribution
Jul 2011 • Couples
My sister, girlfriend and I were visiting Montauk for the first time this 4th of July when I decided not to spend another day roasting on the beach but to get out on the water, specifically looking for a little sailing adventure. I first called a larger charterer at Sailing Montauk (vs. Sail Montauk, reviewed here), and was referred by the captain there to Darius at Sail Montauk. Darius was extremely friendly on the phone and reassuring when it came to our fears of getting flipped. He promised me that his Catalina 22s are very stable and that there's essentially no risk of being tossed into the water, while at the same time, the boats are small enough that novices can get a decent feel for sailing the boat. Darius was waiting for us at the Crabby Cowboy well before our meeting time and had the boat ready to go. He gave us a little lesson on raising the sails and we were off. Winds were strong, and Darius was a very entertaining and accommodating instructor, allowing my group to steer the boat and manage the sails. He even had some drinks and snacks for us. Because Darius didn't have another charter until a little later in the evening, he allowed us to sail longer than our allotted time. The experience was really perfect, and the Crabby Cowboy was a terrific spot to grab a few beers after the sail. I'll definitely be giving Darius a call again next time I'm in Montauk.
Written July 7, 2011
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Susan H
New York City, NY7 contributions
Sep 2018 • Couples
What a great way to celebrate the end of summer. If you are looking for a party boat this is not it. It is a small, sweet sailboat with a great captain (Brian!) who plays good music, has great conversation and shares his love of sailing with you for 2 blissful hours at sea.
Written September 18, 2018
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
We loved having you aboard!
Written March 18, 2019
This response is the subjective opinion of the management representative and not of Tripadvisor LLC.
Aarya R
Bengaluru, India9 contributions
May 2017 • Family
The best thing I did in montauk, and sailing now is a memory I will keep as our instructor Darius made our experience very fun and easy! Would love to come back to montauk just for this! Thank you Darius!
Written May 25, 2017
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Melissa R
2 contributions
Aug 2016 • Friends
I've always dreamed of sailing and our sunset sail with Captain Seth exceeding my expectations. Not only did my friends and I have a blast, I also learned about sailing and even got to perform some of the moves myself. Seth rolled with our music tastes and really showed us a good time. I highly recommend this sailing adventure and cannot wait to book another trip when I visit again.
Written September 2, 2016
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
oatmeal922
New York City, NY1 contribution
Aug 2016 • Family
Everyone was so professional and great to work with. Our sunset sail was perfect for the family and when my kids 3 & 6 lost interest about an hour into the trip, our guide brought out water guns which made it enjoyable for all. highly recommend!
Written August 30, 2016
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
PhoenixCam
Hempstead, NY2 contributions
Jun 2016 • Couples
My kids and I bought a 2 hour session for my husband as a Father's Day gift. My husband and I absolutely loved the whole experience! It was our first time on a sail boat and my husband got to steer the boat the entire time. We had drinks and slowly transitioned into a deep relaxation that lasted the entire day . It was truly memorable and our Captain was delightful! She was so sweet and knowledgeable. We are coming back with our adult children next time!
Written June 22, 2016
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Wear_the_rose
Weybridge, UK59 contributions
Aug 2015 • Couples
Well organised sunset sail. Great views of Montauk and local area. The skipper for the evening was charming and very knowledgeable. A great adventure.
Written October 24, 2015
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
adoraq2015
New York City, New York8 contributions
Aug 2015 • Couples
The guys at sail Montauk just made everything so enjoyable. We had sunset sailing and lessons every week. Will come back and have more next year for sure!
Written September 13, 2015
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
russelljunrath
Union City, New Jersey1 contribution
Aug 2015 • Family
Our guide, Darrius (spelling?) was great! We have twins that are almost 4. He explained about the sail boat to them, had an awesome personality and really made the trip what it was. I would def. do this again and would hope to get him again.
Written August 27, 2015
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Hola muy buenas tardes me gustaria saber si puedo alquilar un bote por 4 horas?
Written July 1, 2019
Hello,
We do 2 and 3 hour private charters. Let me know if you have any other questions or would like to book.
Best,
Emily
Written July 3, 2019
Are sunset sails only available through the summer? My husband and I are looking to book a sunset sail during the first week of October, but the website doesn't look like that is an available time.
Thank you!
Written September 17, 2018
I am not sure of the timing but they do go south to sail during the winter. I would call and ask Darius or Ali how late in the season they will operate out of the Montauk location.
Written September 17, 2018
Is there a catamaran or any boat available for a day-sail for 8 people?
Written March 28, 2016
Hi Ellen,
We do not have a catamaran but for a group your size I would suggest one of our Flotilla Boat Parties. Book multiple boats and sail along side each other flotilla style. Raft up for picnic parties and swimming, experience a head to head race or play cat and mouse with waterguns to gain bragging rights for the season. All of our sails are hands on, so do as much or as little as you want. Perfect for bachelor/bachelorette parties, corporate events, family reunions and team building workshops.
I hope this answers your question!
Written March 29, 2016
Who do we contact to go for sail boat rental? I am new here and today driving from Hamptons to montauk first time ...if u can give phone number or add - many thanks
Written June 3, 2015
Hi Anu,
You can call us at 631-522-5183 with questions or to book, or visit our website and fill out the online reservation form.
Thanks, we hope to have you aboard!
Written June 3, 2015
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