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Open today: 08:00 - 20:00

Sail Montauk
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Traveller Overview
  • Excellent98%
  • Very good1%
  • Average1%
  • Poor0%
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Travellers talk 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...more
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Hours Today: 08:00 - 20:00
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Suggested duration: 2-3 hours
32 Star Island Rd, Slip 412, Montauk, NY 11954-5271
+1 631-522-5183
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Reviews (140)
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All reviews amazing experience actual experience great teacher great conversation trip enjoyable bring your own alcohol beautiful sunset awesome captain fun experience bachelorette party two hours ali lesson ally boats instructor flotilla
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1 - 10 of 140 reviews
Reviewed 19 September 2018

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...More

Date of experience: September 2018
Thank Susan H
Reviewed 8 September 2018

Beautiful two hours! Lesson in sailing, very comfortable and very pleasant female Captain. Will recommend to friends!

Review collected in partnership with this attraction
Date of experience: August 2018
Thank Joann S
Reviewed 8 September 2018

Went sailing on our 1st anniversary and came back for the 4th this summer. Such an excellent time! Will be back next summer for sure!

Review collected in partnership with this attraction
Date of experience: August 2018
Thank mblack9664
Reviewed 7 September 2018

Sail with this crew and you will not only have the best time, you will learn a lot about Montauk. Professional and chill, best day ever!

Review collected in partnership with this attraction
Date of experience: August 2018
Thank F404BLlauraf
Reviewed 3 September 2018 via mobile

One of the Best Things I Did in the Hamptons this Summer! After a 5-day sailing course at Montauk Sailing, I earned my basic sailing certification. Ally (and her husband, Darius) are both such genuine, nice people and patient instructors. And how can you beat...More

Date of experience: August 2018
Thank staciem211
Reviewed 28 August 2018 via mobile

We had a great time last evening with Darius as our captain for a sunset sail. Thank you for the great time and conversation and for teaching us a little bit about sailing!!

Date of experience: August 2018
Thank 998timothyt
Reviewed 25 August 2018 via mobile

My girlfriend and I had a fun and very enjoyable sunset cruise. You can bring your own alcohol and food. Plus the captain let's you control the boat and teach you about sailing if you like. Very friendly, made me and my girlfriend want to...More

Date of experience: August 2018
Thank Sigmund F
Reviewed 10 August 2018 via mobile

Myself and 7 other friends rented 2 sailboats for a flotilla party and it was one of the best things we’ve done all summer! Darius and Lauren were great captains and really facilitated an amazing experience. While booking, I spoke with Allie who was very...More

Date of experience: August 2018
Thank nejlarenee
Reviewed 7 August 2018 via mobile

Everyone we met was fantastic! We had a wonderful, relaxing, beautiful sunset cruise with a very accommodating captain. A good time was had by all, highly recommend!

Date of experience: August 2018
Thank mikewanich1
Reviewed 1 August 2018

We've been sailing Sail Montauk every summer for 5 years now. The owners and the crew are wonderful and accommodating to your desires (music? no music? sail in the lake or not?).

Review collected in partnership with this attraction
Date of experience: July 2018
Thank tonicortese9194
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Questions & Answers
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Amanda S
17 September 2018|
Response from 998timothyt | Reviewed this property |
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.
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!