Sail Montauk
Boat Tours • Lessons & Workshops • Boat Rentals
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8:00 AM - 8:00 PM
Monday
8:00 AM - 8:00 PM
Tuesday
8:00 AM - 8:00 PM
Wednesday
8:00 AM - 8:00 PM
Thursday
8:00 AM - 8:00 PM
Friday
8:00 AM - 8:00 PM
Saturday
8:00 AM - 8:00 PM
Sunday
8:00 AM - 7:00 PM
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 sails, or spend some more time on the water with a Sail & Swim package. Book a 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.
Montauk, New York

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Detailed Reviews: Reviews order informed by descriptiveness of user-identified themes such as cleanliness, atmosphere, general tips and location information.

5.0
241 reviews
Excellent
237
Very good
2
Average
2
Poor
0
Terrible
0

David James
World5 contributions
Aug 2022 • Friends
Last night, our group of four took off at 6 for a two hour ride on the sound around Montauk. Julian was our guide, and was an absolute treat. He was knowledgeable about the area, the boats, and was considerate to everyone on board.
The boat was well sized for a group of 4, I could see up to 8 people comfortably fitting inside and outside of the boat. Everything was immaculately clean and safe.
The trip itself lasted perfectly into the sunset, and ended with a moonrise just before the sturgeon super moon.
Amenities provided worked great! They do suggest going to the bathroom before the trip, and that’s a pretty fair warning. I would keep your cooler size to something mid-range. We brought a massive cooler and really didn’t need it, but that’s on us. There is a Bluetooth speaker on board, works great.
Overall 10/10, absolutely would take this trip again, and even the owners offered well-wishes on our return.
Written August 11, 2022
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.

Michael D
West Orange, NJ2 contributions
Jun 2022 • Couples
My girlfriend and I did the sunset cruise. It was the first time on a sail for both of us and we both enjoyed it very much. Our captain took us back and forth across Lake Montauk, then we took a trip out into the Bay Area where the water was a bit more exciting. We both had a lot of fun and will definitely be coming back next time we visit Montauk.
Written June 25, 2022
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.

Donna L
3 contributions
Aug 2022 • Couples
Sail Montauk was a very simple easy sail experience. Peter was an awesome captain we enjoyed the lake. 2 hours was perfect timing rather than other sail companies where you have to commit to 5 hours. We had an awesome time!
Written August 30, 2022
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.

Katiep0524
2 contributions
Jun 2022 • Couples
We booked the 6pm sunset cruise and it was such a wonderful experience! Ali was our captain and she was so friendly and knowledgeable. She interacted with us when we had questions or was sharing something interesting and also sat back let us enjoy ourselves, it was perfect!

We lucked out with amazing weather and smooth waters so it really made for an awesome night. We split the cost with another couple and felt it was so well priced considering it's the hamptons and it was worth every dollar! Would recommend booking with Sail Montauk if you're thinking about it as we'd absolutely book with them again in the future.
Written June 19, 2022
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.

REBLE
New York City, NY82 contributions
Jun 2022
The weather was beautiful and so was the sunset cruise. Captain Alley was informative which made for a pleasurable sail around Lake Montauk . I recommend this trip to all couples looking for an enjoyable time on the water.
Written June 12, 2022
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.

Marilyn S
Normandy beach3 contributions
Aug 2022 • Couples
Our captain Declan was wonderful. Perfect amount of time to cruise around and catch a beautiful sunset. We left our basket of cheese and wine and they immediately called us and put the cheese I. Their fridge until we could grab in the morning!
Written August 26, 2022
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.

MamaMamiNJ
2 contributions
Aug 2022 • Family
Captains Peter and Ali took our family of four and five other friends for a fun two boat Sunset Sail. The children (all strong swimmers with some sail experience) loved it, even swimming off the boat and trying to attack us with water guns! We sailed the Lake and watched the sunset over the sound. It was perfect. I highly recommend this activity for anyone.
Written August 30, 2022
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.

Natalia
New York City, NY2 contributions
Jun 2022 • Family
Highly recommend this experience. We decided to take advantage of an opportunity to go sailing as part of our stay in Montauk and it was the highlight of our trip. The team at Sail Montauk are so friendly, professional and accommodating. This was our first time sailing and we enjoyed every minute. The sunset was beautiful, the vibes were perfect and we will absolutely do this again. It was just us two and our daughter along with our awesome captain Julian, so we just talked about life and plans and soaked up the beautiful views. You can bring drinks and snacks and a playlist, but you will be ok if you don’t, there is complementary water provided. Make sure to bring a sweater or a hoodie, the day we went it was 68 degrees and we were perfectly dressed in jeans and hoodies to be comfortable. On our way back we even enjoyed encountering a seal - one of two who live in the harbor. Very special. Loved it!
Written June 24, 2022
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.

Holly P
New York City, NY1 contribution
Jun 2022
I didn't know what to expect taking a trip on a sailboat.. IT EXCEEDED MY EXPECTATIONS! My friends and I had the best time. We were there for a very small bachelorette weekend. We were first welcomed with open arms and our items were put into a cooler on the sailboat. The sail was overall very relaxing and I would choose sailing over a bigger boat any day after this experience. Julian was awesome and was basically part of our crew. The weather was just right to jump in the water after anchoring.. the water was frigid but we enjoyed a short dip with noodles and water guns. I would truly recommend this. I go out to Montauk every summer and I want to do this excursion every time. :)
Written June 24, 2022
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.

Melissa W
7 contributions
Sep 2022
My husband and I took a lovely sunset sail with Peter. This was our first time sailing and we got to sit back and relax while learning about the boat and the tasks involved. The entire crew were nice and friendly and made it a great experience! We had amazing weather and views and were in great hands for our experience! We highly recommend the sailing experience!
Written September 11, 2022
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.

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Sail Montauk - All You Need to Know BEFORE You Go (with Photos)