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    Sail Montauk

    5.0 (38 reviews)
    Closed 9:00 am - 8:00 pm

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    Services - Sail Montauk

    Boat charters

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    Relaxing day off the coast of Montauk!
    Eileen C.

    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.

    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!

    View from the harbor
    Kyle K.

    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!

    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.

    Heather W.

    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!

    Amazing sail with cap . Josh
    Kimmee A.

    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.

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    5 years ago

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    12 years ago

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    Emily H.

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    5 years ago

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

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    11 years ago

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    9 years ago

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    8 years ago

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

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    Emily H.

    We loved having your family aboard! Hope to see you soon!

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    10 years ago

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

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    Review Highlights - Sail Montauk

    Darius kept it interesting and exciting and let them participate in the sailing.

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    Flying Cloud Of Montauk

    Flying Cloud Of Montauk

    (1 review)

    My family and I had the best time fishing on the Flying Cloud. Flying Cloud is just one of many…read morecharter boats that offer half day fishing trips, but I chose Flying Cloud because they have a website and they responded to my inquiry email promptly. The Flying Cloud goes out twice a day* and it's $45/person. All tackle and bait is included. We decided to go on the afternoon fishing trip; there were three other small groups on the boat with us but it wasn't crowded at all. Since only three out of our group of four was planning to fish, they were nice enough to only charge us for three people. If you're a first timer at fishing make sure you let them know and someone will give you a crash course when you get on the boat, i.e. how to bait your hook and how to properly drop your line into the sea until the sinker hits the bottom. The Flying Cloud crew was really great. http://www.yelp.com/biz_photos/AoCYQVrX1vau-qbbIUjyyA?select=hRKuruRk5spEQPXZdIX5JQ Capt. Fred Bird drove the boat and took charge of when and where to move spots**. He mostly stayed up above, "DJ-ing" our fishing trip soundtrack and telling us funny stories while we fished. Capt. Neil Nixon was really a pleasure to have in charge. He was very perceptive in his supervising, chatting with the chattier guests on the boat and always ready with the net when someone was reeling in a big one. I appreciated the fact that he let us learn from experience, offering handy tips each time he walked by and only stepping in when we needed help. Capt. Neil also scales and guts the fish that are caught. http://www.yelp.com/biz_photos/AoCYQVrX1vau-qbbIUjyyA?select=ZVa14NtlGilTToxyYtIzSA Some people requested their fish filleted, but we opted to have the bass my sister caught whole. http://www.yelp.com/biz_photos/AoCYQVrX1vau-qbbIUjyyA?select=kT09jFmE9xNqqE81RQ443Q It was turned into Chinese-style steamed bass and fish head stew the next day. Delicious! A couple tips: 1. Even if it's overcast (which it was) you can still get sunburned (which I did) so remember to put on sunblock! 2. If you're prone to seasickness, pack some dramamine in case you need it and don't eat too much before the trip. I started to feel sick after the boat stopped for the first time and it lasted almost an hour before it went away. 3. Bring rags because things will get messy. The pro fishers on board all knew this. 4. Pack some snacks. They sell some on board but it's all overpriced (e.g. $2 for a can of soda). 5. Bring your camera! If you catch a fish you'll definitely want a picture of the moment. Plus, you'll have a great view of the Montauk Point Lighthouse from the boat. Despite getting sunburned and seasick for a part of the time, this was easily my favorite part of our Montauk vacation. Thank you Flying Cloud crew! *8AM - 12PM and 1PM - 5PM **We moved spots about 5 times, either after someone caught a fish or if we were in a spot for a long time without catching something.

    Sail Montauk - boating - Updated May 2026

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