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Sail Montauk

32 Star Island Rd, Slip 412, Montauk, NY 11954-5271
+1 631-522-5183
Review Highlights
Great unique Montauk experience

We did a sailing tour with a large group. We had 3 separate sail boats that sailed separately then... read more

Reviewed 3 weeks ago
Rebecca B
Awesome Sailing Experience

We sailed on a sunset cruise with Darius and can't say enough nice things about the experience. He... read more

Reviewed 3 weeks ago
via mobile
Read all 105 reviews
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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.
  • Excellent98%
  • Very good1%
  • Average1%
  • Poor0%
  • Terrible0%
Travellers talk about
Closed Now
All hours
Hours Today: 10:00 - 19:00
Suggested Duration: 2-3 hours
32 Star Island Rd, Slip 412, Montauk, NY 11954-5271
+1 631-522-5183
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Reviews (105)
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1 - 10 of 105 reviews

Reviewed 3 weeks ago

We did a sailing tour with a large group. We had 3 separate sail boats that sailed separately then were tied together at Navy Beach. Crew is amazing and super experienced. Great adventure and highly recommended!

Thank Rebecca B
Reviewed 3 weeks ago via mobile

We sailed on a sunset cruise with Darius and can't say enough nice things about the experience. He encouraged me to take the helm for most of the sail with just a bit of his guidance and it ended up being really fabulous. Unlike most...More

Thank CT-Freeze
Reviewed 25 May 2017 via mobile

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!

2  Thank Aarya R
Reviewed 11 September 2016

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.

1  Thank JA33609
Reviewed 6 September 2016

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...More

1  Thank mark e
Reviewed 4 September 2016

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...More

1  Thank patrickmullin2016
Reviewed 2 September 2016

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...More

2  Thank Melissa R
Reviewed 31 August 2016

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...More

1  Thank tiffabf
Reviewed 30 August 2016

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...More

1  Thank mtkyoga
Reviewed 30 August 2016

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...More

2  Thank oatmeal922
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Ask a question
Questions & Answers
Ellen C
28 March 2016|
AnswerShow all 2 answers
Response from Kathy H | Property representative |
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... More
3 June 2015|
Response from Kathy H | Property representative |
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!