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. read more

See all

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. read more

A must do when in Montauk. Great sailing experience! Will be back, enjoyed every minute of it. read more

See all

I've been meaning to write this review for several weeks... We booked a sailboat on the 4th of July in the Hamptons, and Sail Montauk was an excellent choice. First of all, they're based out of the beautiful Montauk Yacht Club. Next, the staff are top notch. Our captain was a full time firefighter for the Queens Fire Department, and was a friendly guide on our sailing excursion. The weather was wonderful, and it was such a nice break from the hustle of New York City! They provide an ice chest full of ice and water on the boat. You're welcome to BYOB and pop it in the cooler. One thing to remember though is there is no restroom on the sailboat -- so take it easy on guzzling the beverages while on board! The sailboat charter is as hands on (or hands off) as you'd like. My two daughters took charge of the sailboat for a bit, and learned a bit about sailing. Whereas my husband and I just sat back and relaxed. My kids also liked the fact that they got to hook up their phone to the on board music player and they picked the music for the trip. Overall, we had an amazing experience and we'd definitely do it again. read more

Sail Montauk - Relaxing day off the coast of Montauk! - Boating Near Me - Montauk, New York

See all

Our family of 5 (2 adults, 3 kids ages 13, 10, and 3) had an amazing afternoon sailing aboard Ol' Blue with Captain Julian today. The boat was impeccably clean. Stocked with ice, water, cups, and a great sailing soundtrack. We brought snacks and adult beverages and made ourselves comfortable. We started in Lake Montauk, where Julian found us a nice spot to anchor and swim around. The boat had pool noodles and water shooting toys. After about an hour, we set sail again, heading out into Long Island Sound for a bit before heading back to port. Overall, we had a fabulous experience. Julian was knowledgeable, friendly, and inclusive with the kids. We can't wait to book again next summer! Thank you Sail Montauk for a fabulous experience! read more

See all

Saul montauk is the best! My bridesmaids and I (6 total) went out for one day on my bachelorette trip and had the BEST time. Our captain was great and it was such a nice relaxing day! Would recommend this to anyone looking for an activity in Montauk read more

We went sailing yesterday and it was a great experience! We loved it and will definitely do again next time we're in Montauk. Ally was knowledgeable, friendly and extremely accommodating! Would highly recommend. read more

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! read more

See all

What a fun experience! Highly recommend Sail Montauk if you're looking for a day out on the water. The booking process was super easy and they did a great job getting my two kids (who have never sailed before) familiar with the boat. The Taste of Sailing experience was perfect for our 9 and 6 year old, who both had a chance to steer the boat. The boat was in absolutely perfect condition. Captain Ali was so personable and friendly and did an awesome job engaging the little ones. It was just a really special and memorable experience to watch my daughter get a sailing lesson from her grandfather and I'm so thankful to Sail Montauk for making it such a wonderful experience. This was a memory our family will have forever. read more

See all

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! read more

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. read more

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! read more

Sail Montauk - Boating Near Me - Montauk, New York

See all

Gave a "Swim Package" as a B Day present to my boyfriend. We loved every min of the trip. Sail Montauk is a great adventure, you can choose how much u want to sail or you can leave it up to the Cap. But I recommend sharing in the sailing because it's a wonderful way to spend an afternoon. You walk away with a great experience. read more

Sail Montauk - Amazing sail with cap . Josh - Boating Near Me - Montauk, New York

I went to Montauk for the first time for my sister's bachelorette. There were nine girls and we chose the tandem sailing option through Sail Montauk. It was very relaxing and fun. Darius, the owner, responded faster than other companies which I appreciated. His co-captain, Josh was very chill. Darius had good energy and was enthusiastic. He taught the girls how to sail and allowed them to take part in the sailing experience. We had really good wind that day and so it worked out well. I would definitely recommend this for a bachelorette party. Make sure to bring food/snacks with you. We had taken our own cooler full of prosciutto, provolone cheese, italian bread with arugula. We also made tuna salad...actually one one of us made it ...and it wasn't me. When we were anchored, both our boats were tied together and we were able to walk over each others boats and just enjoy the food and sun. Beers and wine should be mandatory. read more

Dear Sail Montauk, Thank you for existing!! You all are so talented at what you do, and appears you have tons of fun sharing your skill. What a great way to spend a couple of hours! I'll be back. read more

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 :) read more

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 the harbor with calmer water. In another 30 minutes, we anchored (is that the right word?) and we all jumped into the lake! We all had a great and amazing time. At one point, there was another party boat around and some of the guys kayaked over and started telling us how they did the same thing 2 weeks ago and saw like 50 dolphins! You can help out with the sails but you don't have to. All of this is cost us about $115 per person including tip!! How great is that! This is staying on my summer list from now on. read more

See all

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. read more

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!! read more

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! read more

A must do when in Montauk. A fun and informative experience. Will definitely visit again.

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! read more

MONTAUK may be know for its fishing, there is still room for sailors. Located on the north side of the Montauk Yacht Club, myself along with my son (18), daughter (14), and nephew (10), had an excellent afternoon with a bareboat rental. The staff is wonderful, the boat in perfect working order, and the location works for both Jr and seasoned sailors. We started in the lake where we went to shakedown the crew (kids). After sorting out positions, reviewing the protocol for adressing the skipper, and putting a few tacks, we were ready to head out thru the channel into the sound. Note that the boat is setup for single handed sailing, but we divided duties to make it more interesting and perhaps create more Jr sailors. As it turned out there was allot more wind (10 knots with gusts to around 14), in the lake with all sorts of interesting wind shifts. In the sound it was a consistent 8 to 10 knot southerly with mostly flat seas. Perfect for an afternoon cruse with snacks and other nautical nonsense . We all took turns driving, worked on our tacks and again reminded the crew how the skipper is the absolute authority on the boat. Registration was easy. Having never rented a bareboat before I went the day before for the checkout sail with Ali (great instructor/coach). I was probably over thinking it, since the alternative in the event I did not checkout would be to bring along an instructor. I would certainly recommend this experience to any sailors visiting Montauk. read more

Sail Montauk - Our Crew.. - Boating Near Me - Montauk, New York

Rented a bareboat Catalina 22 from Sail Montauk on 07/20/2016 for a sail with my 13yo daughter. The boat was in great shape for the amount of use it must get, had a new outboard engine and well rigged for me to sail single handed while teaching my daughter to sail something bigger then she has sailed before. They supply a VHF radio, handheld depth finder, Bluetooth speaker, cooler with ice and drinks, and made sure the fuel tank was topped off. The staff was more then friendly and helpful while at the same time evaluating me, my sailing experience and knowledge of the harbor, lake and bay. At the end of the day the staff met us at the dock and were genuinely interested in how our day and sail went. I would recommend this company to anybody looking for a great bareboat rental, sailing lesson, or charter. read more

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. read more

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

Great experience!! Awesome husband and wife duo. We got to participate in the sailing and also sit and relax on the bow. Definitely worth doing next time you're out in Montauk!! read more

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. read more

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! read more

Seriously the nicest and most helpful people I could ask for. Long story short, I got engaged on one of their sunset cruises (which I highly recommend-- great experience and very reasonably priced), and everyone at the company worked really hard to make sure it occurred without a hitch. Oh, and my original plan fell through at the last moment, so they arranged everything within 24 hours. A special shout-out to Emily and Captain Martin whom I met, and I could tell they really love what they do, and want everyone to enjoy their experience to the fullest. Thank you guys!!! You really are awesome! read more

I love Sail Montauk! I have done a number of their sailing packages and it has been nothing short of amazing! I first went on a Sail & Swim and had a blast! Having never been sailing before, I was a bit nervous, but our captain Ali showed us around the boat, explained the basics of sailing, and was so patient and a great teacher. She even had time to give us some local tips on what to do/where to eat/what we couldn't miss in Montauk, which I appreciated as someone who had never been there before. They took us to a great swimming spot too! We had a blast! I loved it so much that I went back that same week for one of their Tuesday Night Regatta races. I went solo (my friends opted to watch from the main boat) but it didn't matter because the captain, this time Darius, did a great job of making us feel like a team right from the start--which is good because were actually sailing the boat for the races! After a quick refresher (Darius is also a great teacher) we were off! By the end of the 3 races, I felt like a professional and I didn't want it to end! Even though we didn't win (3rd place!) I had so much fun! And my teammates and I hung out at the bar afterwards for pizza, beer, and an awards ceremony. What a great experience! Also they were so nice and accommodating when we made our bookings. They returned my call quickly and answered all of my questions! I DEFINITELY recommend! And I will DEFINITELY be back! THANKS SAIL MONTAUK!! read more

We had a beautiful time on our sail bought!! We went at 6 to 8 and the sunset was just beautiful will deff do this again next time we visit montauk! read more

Sail Montauk - Boating Near Me - Montauk, New York

See all

Sail Montauk was awesome! The day our trip was planned for, the weather wasn't perfect and Emily called us in the morning to see if we still wanted to head out, which was great. We found the dock & boat slip with ease and was greeted by Emily. We then signed a waiver and were off sailing with our wonderful captain Ali. Ali was awesome. There were 3 of us on the boat, which didn't make it crowded. Ali did most of the work but then let me steer, which I had fun doing. She played awesome music the whole time, which made it more enjoyable. We brought our own beers and champagne, but had the option to drink their iced tea and waters. When we dropped anchor, Ali did all the work again and then we enjoyed a swim in the water. It turned out to be the perfect day for sailing in my opinion. I vacation in Montauk every summer and this was the first time doing Sail Montauk, but I would definitely make it a routine thing because it was that great! This particular trip was most memorable because my girlfriend proposed while we were at anchor and Ali & Emily helped make the day so special for us. I highly recommend Sail Montauk and can't wait to do the "Sunset Cruise" next. read more

Amazing! My wife and I did the sunset sail and had a great time sailing around the sound. The boats are beautiful and come well stocked and well prepared. The staff does all the work and you can just enjoy if you chose! We happened to be sailors and enjoyed taking the helm ourselves for a good chunk of the ride. The crew at Sail Montauk is amazing and very accommodating to what you wish to do. read more

Sail Montauk - Enjoying some local beer we picked up in town. - Boating Near Me - Montauk, New York

See all

This was an awesome experience ! We didn't have too much wind on our day but we were able to pop out another sail and cruise around the lake! Darius was a great trainer and taught us really well. It was a lot of fun, and we will definitely do it again. PS: they have speakers on each boat so don't forget to request the calypso music read more

Our Captain, Ali was warm, accommodating and a great sailing teacher. We spent a wonderful couple of hours sailing around the Sound as part of our honeymoon. Couldn't recommend it more as a great way to top off a trip to Montauk! read more

Four of us went out with Sail Montauk Sunday of Labor Day weekend and had the most amazing time. The boat was great and well stocked with water and sodas (which we barely touched as we brought a boat-load of rose) and Captain Darius was fantastic. We sailed through Lake Montauk and out into Block Island Sound. That portion was much more adventurous and a lot of fun. I tend to get sea sick, so when that happened, the Captain turned us around and headed back into the calmer seas of Lake Montauk where we anchored and were able to jump out for a swim. Honestly cannot say enough positive things about this company. From the initial scheduling to the actual sail, it was A+. We're actually thinking of joining him for a sail down in the Caribbean this winter! read more

We did the sail & swim and had the best time. Captain Felix was great and would recommend sailing with this company to anyone interested.