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

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 102 reviews
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  • 99
    Excellent
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    Very good
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Very friendly staff

Ali and the team are very friendly and all of their equipment is in tip top shape. Definitely a positive to have new outboards that turn over easily.

5 of 5 starsReviewed 2 weeks ago
JA33609
,
Tampa, Kansas
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102 Reviews from our TripAdvisor Community

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Showing 102: English reviews
Tampa, Kansas
1 review
5 of 5 stars Reviewed 2 weeks ago

Ali and the team are very friendly and all of their equipment is in tip top shape. Definitely a positive to have new outboards that turn over easily.

Helpful?
Thank JA33609
Level Contributor
7 reviews
5 attraction reviews
common_n_attraction_reviews_1bd8 7 helpful votes
5 of 5 stars Reviewed 3 weeks ago

Fantastic sunset sail manned by Captain Darius. Weather was perfect, the sunset gorgeous, the wind just the right velocity....what more could you ask for? Oh, how about a knowledgeable, charming and funny Captain to help make the 2 hour sail so enjoyable. Darius is The Man, and he encouraged us (there were 3 of us) to handle the rudder and... More 

Helpful?
Thank mark e
New York City, New York
1 review
5 of 5 stars Reviewed 3 weeks ago

The three of us sailed for 2 hours with Ali at the helm on a Friday evening. There was plenty of room for all of us as we sailed in the inner inlet and then out to Block Island Sound. The sunset was awe inspiring and the waters very calm. Ali was terrific and made us feel very comfortable. This... More 

Helpful?
Thank patrickmullin2016
2 reviews
5 of 5 stars Reviewed 4 weeks ago

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... More 

Helpful?
Thank Melissa R
New York City, New York
1 review
5 of 5 stars Reviewed 4 weeks ago

I treated my best friend to a little sailing adventure. I chose Sail Montauk. This was the most amazing experience. Both of us couldn't have asked for a better time. Aly was super helpful and our Captain, Darius was fantastic- he was experienced, friendly and gave us history about Montauk, and suggested other fun activities for our Day Trip. We... More 

Helpful?
Thank tiffabf
Montauk, New York
2 reviews
common_n_attraction_reviews_1bd8 1 helpful vote
5 of 5 stars Reviewed 4 weeks ago

Our Captain, Ali, is gracious, knowledgable and fun to be out with on the water. Since my children have gone to sailing school with her, she continues to teach them when they are out on a casual sail. We went from Lake Montauk out of the harbor and stayed north of Culloden and then east towards the lighthouse. It was... More 

Helpful?
Thank mtkyoga
New York City, New York
1 review
5 of 5 stars Reviewed 4 weeks ago

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!

Helpful?
Thank oatmeal922
Level Contributor
10 reviews
common_n_attraction_reviews_1bd8 1 helpful vote
5 of 5 stars Reviewed 4 weeks ago via mobile

My boyfriend and I went on a sunset cruise for my 30th birthday. It was simply amazing! The experience was wonderful from start to finish. You can book online and receive confirmation within a hour. Bring your snacks and wine (champagne for me!). Come with your phone fully charged to take memorable photos and videos. My phone died during the... More 

Helpful?
Thank Channell M
New York City, New York
1 review
5 of 5 stars Reviewed August 24, 2016

It's absolutely worth sailing with Sail Montauk. It was a first time out to Montauk for my sister and I, and we absolutely loved the experience. We did the sunset cruise, it goes from 6pm-8pm on a sail boat. It's a small intimate boat that comes with a cooler to bring your own drinks, they provide you with Honest tea,... More 

Helpful?
Thank heynatalie18
NJ
Level Contributor
134 reviews
47 attraction reviews
common_n_attraction_reviews_1bd8 46 helpful votes
5 of 5 stars Reviewed August 16, 2016 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

Helpful?
Thank CMSCLS

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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?