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Address: 32 Star Island Road, Slip 412, Montauk, NY 11954
Phone Number: +1 631-522-5183
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Today
10:00 am - 7:00 pm
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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...
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

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Great sailing experience!

We booked an evening sail, saw the most beautiful sunset. So nice to experience an amazing sailing with just your family of three onboard. Very intimate and relaxing.

Review collected in partnership with this attraction

5 of 5 starsReviewed August 27, 2015
,
bedford new york
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74 Reviews from our TripAdvisor Community

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Date | Rating
  • English first
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English first
bedford new york
Level Contributor
17 reviews
common_n_attraction_reviews_1bd8 6 helpful votes
5 of 5 stars Reviewed August 27, 2015 NEW

We booked an evening sail, saw the most beautiful sunset. So nice to experience an amazing sailing with just your family of three onboard. Very intimate and relaxing.

Review collected in partnership with this attraction

Was this review helpful? Yes
Union City, New Jersey
1 review
5 of 5 stars Reviewed August 27, 2015 NEW

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.

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Luxembourg District, Luxembourg
1 review
5 of 5 stars Reviewed August 26, 2015 NEW

A top rated event in Montauk, our highlight of the week. Easy booking, warm welcome, easy going team. I could steer the boat throughout the sailing time. Our captain Ally was just perfect : light touch, smile, nice company. All you need is a bathing suit, a camera and your favourite beverage. I recommend to everyone, every age. Can't wait... More 

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Queens, New York
1 review
5 of 5 stars Reviewed August 22, 2015 NEW

I will deficient my recommend. Me and my boyfriend had a great time. I would love to do it again. So fun!!

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Sag Harbor, New York
1 review
5 of 5 stars Reviewed August 22, 2015 NEW

Engaging captain (Darius) and perfect boat for a family of four. Highly recommended for an introduction to sailing.

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Brooklyn, New York
1 review
5 of 5 stars Reviewed August 19, 2015

What a lovely evening! We took a sunset sail and saw a pod of around fifty dolphins feeding. Our captain Ali followed them so we were surrounded by them throughout our sail. Ali was very fun and knowledgeable - she even let me steer the boat! The boat was clean, and they provided refreshments. We were also able to bring... More 

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Greenville, South Carolina
1 review
5 of 5 stars Reviewed August 16, 2015

What a great sailing trip out of Montauk! Ali was a great skipper, the boat was clean and comfortable and the experience was so relaxing. I would definitely recommend Sail Montauk to anyone who loves sailing or who wants to experience it for the first time.

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Montrose
1 review
5 of 5 stars Reviewed August 13, 2015

My family- consisting of my wife, 30 year old son, his girlfriend and best friend, we're looking for a special experience to celebrate our son's best friend's special 30th birthday. We found it on the waters of Montauk. Our very skilled, very personable and knowledgeable captain (Seth) was engaging and sympathetic to the choppy travel as he navigated us back... More 

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Chicago
1 review
5 of 5 stars Reviewed August 12, 2015

This was a delightful way to spend an afternoon! We chartered two boats, and our captains, Ally and Darius, were so much fun and complete professionals! The route around the lake was beautiful, and our guides were quite knowledgeable about the surrounding Montauk area, as well as sailing, in general. They were great with our kids, all of whom LOVED... More 

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Montreal, Quebec
1 review
5 of 5 stars Reviewed August 8, 2015

We enjoyed our time out. Everyone got to steer the boat when they wanted, but the friendly guide would handle the boat if we'd rather sit back with a beer. Both my dad who has been sailing for the past 30 years and mom who is usually quite scared on a boat had a great time. Highly recommended.

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Questions & Answers

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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?