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Address: 32 Star Island Rd, Slip 412, Montauk, NY 11954-5271
Phone Number: +1 631-522-5183
10:00 am - 7:00 pm
Closed now
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Sun - Sat 10:00 am - 7:00 pm
Recommended length of visit: 2-3 hours

Step off the dock and onto one of our private sailboats for an exhilarating...

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. Groups can enjoy a Flotilla Boat Party, perfect for large groups, reunions and team building events. Basic Sailing Courses and our Junior Sailing Program offer a chance to learn to sail, and 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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TripAdvisor Reviewer Highlights

Read all 93 reviews
Visitor rating
  • 90
  • 1
    Very good
  • 2
  • 0
  • 0
Wonderful morning at sea

Great time w Felix..relaxed, easy going and just fun! Got to learn a little about sailing, swam a bit, brought great tunes and just relaxed

5 of 5 starsReviewed 1 week ago
via mobile
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93 Reviews from our TripAdvisor Community

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Showing 93: English reviews
Level Contributor
134 reviews
47 attraction reviews
common_n_attraction_reviews_1bd8 44 helpful votes
5 of 5 stars Reviewed 1 week ago via mobile

Great time w Felix..relaxed, easy going and just fun! Got to learn a little about sailing, swam a bit, brought great tunes and just relaxed

New York City
2 reviews
5 of 5 stars Reviewed 2 weeks ago

Easy to book (credit card over the phone). Easy to find. Showed up and got right on the boat. Darius (captain) was fantastic. Knew all about Montauk and sailing. Taught us how to sail, but also let us relax and enjoy the sunset. Perfect evening. Highly recommended.

Thank waxy_maize
1 review
5 of 5 stars Reviewed 3 weeks ago

They have a variety of options available. Bare-boat sailing (no Captain) with a Captain, lessons, Sunset Cruises, etc. As I have sailing experience I did the bare-boat option. They checked out my abilities and then watched us set off. The staff were professional, but also very cool. The sail was reduced or reefed due to a decent amount of wind.... More 

Thank William P
Montauk, New York
1 review
5 of 5 stars Reviewed 4 weeks ago

Darius was an excellent captain and guide on our afternoon sail to a private cove. The water was crystal clear and swimming was awesome. The Jimmy Buffet sighting was an added plus! We highly recommend Sail Montauk! Darius and Ali...Congratulations!

Thank RobertandJacqueline
Seattle, Washington
Level Contributor
4 reviews
5 of 5 stars Reviewed June 28, 2016 via mobile

I am so excited to say the Sail Montauk crew was fantastic. Sailing Lake Montauk and Block Island Sound was a first for my daughters who are in their twenties. A weeks vacation in the Hamptons and a visit to Montauk led us directly to Sail Montauk. Seth was very nice and willing to share his vast knowledge of sailing,... More 

Thank RandyI
Hempstead, New York
1 review
common_n_attraction_reviews_1bd8 1 helpful vote
5 of 5 stars Reviewed June 22, 2016

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... More 

1 Thank camillemorrison
Royersford, Pennsylvania
Level Contributor
3 reviews
common_n_attraction_reviews_1bd8 3 helpful votes
5 of 5 stars Reviewed June 1, 2016

Darius was an excellent instructor, very knowledgeable and entertaining! He made our family feel relaxed and we had a lot of laughs along the way! We all can't wait to visit Montauk again! Thanks Sail Montauk!

Thank Margaret L
Hudson Valley, NY
Level Contributor
11 reviews
5 attraction reviews
common_n_attraction_reviews_1bd8 6 helpful votes
5 of 5 stars Reviewed May 25, 2016

If you're looking for a fun way to spend a couple of hours with your friends, family, or partner in Montauk, consider booking a sailing trip with Sail Montauk. I booked the 2-hour Taste of Sailing trip during a recent mother-daughter getaway. The booking process was very easy and there was terrific follow-up via email with the owner, Ali, who... More 

1 Thank Cathy K
long island, new york
Level Contributor
45 reviews
14 attraction reviews
common_n_attraction_reviews_1bd8 21 helpful votes
4 of 5 stars Reviewed April 26, 2016

We were given a gift of a two-day lesson. Darius was an excellent instructor. Sailing isn't easy, but he made it seem fun and stress-free. Keep in mind that the initial certification is not difficult to obtain, but it doesn't mean you're ready to start sailing on your own. It's only the first step.

1 Thank julia m
Sayville, New York
1 review
common_n_attraction_reviews_1bd8 1 helpful vote
5 of 5 stars Reviewed February 2, 2016

Darius made our sunset sail relaxing, fun, so enjoyable. We will definitely do it again. (This was our 2nd sail with him)

Review collected in partnership with this attraction

1 Thank 848moniqueg

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Typical questions asked:
  • Will you pick up and drop off at my hotel?
  • I have a family of 7. Can your tour accommodate all of us together?
  • How should I dress for this tour?