Sail Montauk

We had a great time sailing with Ali. She was very knowledgeable about the area and it's history. It's a great way to spend a few hours on the water while being able to relax and take in the sights, all while sipping a cocktail. Highly recommend Sail Montauk.

Darius is great with kids and people in general. If you have kids then he's the guy to book with because he involves them in the sailing and they have a blast.

We had a great time even though the weather was not perfect which is saying a lot. He put us at ease and gave us just the right amount of information so that we got a sense of the boat and sailing. It was a really nice way to see the area and we'd do it again.

I can't say enough about this company! What an amazing experience. If you are thinking about it, you should do it! I used them for a corporate team building event and everyone raved about it. Start to finish everything was perfect!

This was an amazing experience for my first sailing lesson! with no background at all, Darius, the instructor and owner, did a great job of explaining everything & teaching me about sailing and how a boat works. it was a lot of fun and he was nice enough to refund me $100 because it wasn't windy enough to sail that day, however we stayed on the boat for the full 3 hours to enjoy the water and the sun. would 100% recommend and go back!! :)

My best friends surprised me with a sunset sail for a graduation gift. We sailed with Darius who was extremely fun, professional, and accommodating. Though the weather was not ideal, we had a wonderful time seeing Montauk from the water and got some great photos while we were at it. I will 100% sail with them again when I am back in Montauk!

Our beautiful yacht, Justine, was the perfect backdrop to celebrate our 25th wedding anniversary. We were able to invite a small group of family members to share this special celebration and still be very well spaced out on this gorgeous vessel. The sunset cruise was spectacular and watching the too shores going from dusk to dark was incredible. The staff were all very accommodating and attentive throughout our voyage. I would highly recommend hiring this crew and this yacht for any special occasion!

Positive: Professionalism, Value
Amazing experience loved our captain and felt safe. Wish we booked longer time. Must try.

We had such a great time on our sunset cruise! Ali was so accommodating and you can tell they really enjoy sailing and it was a pleasure to be around the positive energy. Highly recommended and a must do when visiting Montauk!

Great private sunset sail. Brian our Captain was terrific. We picked our music and drank champagne. I have chartered many boats all over the world, I highly recommend Sail Montauk.

Worth every penny. My (now) fiancé and I booked a private sunset cruise the weekend after Labor Day. We were initially worried about the weather, but we lucked out and the evening ended up being an experience we will never forget. The views were stunning and the sail was even more romantic than we could've hoped for. We were even encouraged to bring our own wine and snacks. Most importantly, our captain, Ali was the perfect combination of professional and personable. We will definitely be booking again in the future!

Great experience. I took my girlfriend so it made for a very romantic evening. The captain was very cool and accommodating and took us where we wanted to go, within limits of course. The sunset was spectacular out on the water. Would definitely do it again.

Had a great experience sailing. Would highly recommend for a relaxing time!! Boat was very clean, comfortable. Cooler with ice and water provided. Hook up for your own music playlist (or they provide) and super friendly captain!

Family sailing trip was amazing! Big shout out to Darius (captain) for a excellent first tune ever trip.

Sailing around Montauk is one of those experiences that’s just necessary when visiting the area. Sail Montauk was a great company to choose for the experience - professional, informative, and entertaining! Very pleased and would highly recommend these charters.

This was our 3rd summer doing SailMontauk with our family of 5. We love it so much that we make it a must do during our Montauk visit each year. Every part of the trip is perfect from taking off at the yacht club to being able to explore the Sound and the Lake. The boats are beautiful and clean and they encourage our kids to sit anywhere they like. A highlight is getting to jump off the boat and swim in Lake Montauk. It is a perfect "10" experience and it's absolutely because of Darius and Ali.

Went out with Andrew on sunday and had an awesome time. He was easy going, friendly, and let us sail as much or as little as we wanted. Highly recommend Sail Montauk!! Thanks for a wonderful Father's Day sail!

Great experience! We took a sunset sail with captain Ali, very friendly and experienced sailor! Smooth and beautiful sail around Montauk area. Very good prices of sailing charters!

Took a two-hour private lesson with Darius to refresh some skills and acquire knowledge of local waters. I couldn't be more pleased with the experience. He passed along valuable insights and helped with a few finer points of boat handling. Arrangements were made by phone with Ali, and both she and Darius could not have been more accommodating. Highly recommend for lessons, charter, or a sunset cruise. Great folks who know their stuff!

Booked a 15 person flotilla experience for my birthday celebration in montauk. Sail montauk was friendly, affordable, fun and extremely accommodating. We met at the dock and quickly began our sail with captain Lauren taking us out. We had music set up with the Bluetooth speaker available for all boats. The weather was perfect and the sail was amazing. We had a water gun fight on the water then docked together, took pictures and had snacks. Everyone had so much fun! I will be trying the sunset cruise next...thanks sail montauk for the best birthday sail!

My family and I had a great time with Sail Montauk and Captain Darius. My wife and I took our two young children (2 and 4 years old) and they absolutely loved it. Darius kept it interesting and exciting and let them participate in the sailing. They were also very accommodating with our kids' lunch and many snacks on the boat.
This is very different from something like a river cruise. We've done those before but found sailing to be a unique experience.
My wife and I found it educational and fun and will definitely go back.

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 sail and our captain, Felix, took pics for us. Oh, you can connect your phone via Bluetooth to play music as well. I'll definitely be back to try the daytime sail!
Thank you Darius and Felix for your welcoming hospitality!!

If you are debating whether or not to go with Sail Montauk, think no more! I booked a flotilla boat party for 8 about 2 months in advance so I can secure the labor day Saturday afternoon (2pm-5pm). The registration is pretty simple with google form. We went on 2 boats on a beautiful afternoon. We signed the waiver and got our drinks in the cooler that they provided (and the honest teas and waters that they have), left our shoes in a basket on the pier, and off we go!
We first sailed out of the harbor a little bit, got the waves and the breeze. Then we turned around after 30 min and went back into

Amazing experience with Sail Montauk.
Reasonable pricing and great, new beautiful sail boat. Best of all...the staff and captain Darius was amazing. Great music and perfect sailing skills. Highly recommend!

Awesome ! Super fun experience and friendly staff. We went out into the ocean the bay and the lake went swimming and had a blast

Music can be connected via blue tooth
Soft drinks are provided

Bring a towel and sunblock !

Have fun :)