Sail Montauk

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.

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 :)

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.

Was hoping for a Quiet, Relaxing & Romantic Sunset Cruise, but instead got an awkward, tiring Talk Fest w/​the Captain, for 2 hours. She was about a foot away from us the whole time, which would make smooching or cuddling a little weird & we felt like we had to be «on» the entire time. She was nice & did have some good «Local Eats» & «things to do» suggestions. They only provide sodas & water. For that price, you think they’d offer at least a bottle of something & a couple of snacks. So, we brought our own Wine. It was beautiful being out on the water, but expensive: $ 190.00 plus a 20% tip. We tried to see the good in it. There was good (the sunset was pretty), but overall was disappointed.

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!

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!

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.

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.

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!