CHOOSE YOUR Location

“We recently enjoyed a sunset sail, our first time on the water in the Hamptons despite visiting New York quite often. The views of the coastline were as breathtaking as we had hoped and we had the perfect weather for a smooth cruise with full sails. We were also treated to the most delicious banana bread, made by the stewardess, which was an unexpected delight. We had to ask for the recipe - it was that good. Captain Nate and the crew made everything feel effortless, and the experience was the perfect way to enjoy a private evening sail.”

"Owning a yacht in the Hamptons while living in the city means I can’t always be there to keep up with maintenance. Nate’s Yacht Management team takes care of all the routine upkeep on my 54ft Swan—engine checks, washdowns, and even small repairs—so I can just show up and take the boat out. Never had any problems ever since working with them since July 24."

“We recently had the pleasure of sailing with Nate and it was an unforgettable experience. We explored some incredible spots and the setting was absolutely beautiful. Overall the trip was just so peaceful and fun and I’d 100% recommend booking with him!!!”

“I am so happy I found True Sailing Yacht Management. My boat is in great hands with Nate and his team. They took care of everything while keeping me always updated, without me even having to ask. Whenever I have an issue, Nate picks up the call immediately and usually comes by the same day to take a look. Saved me and my boat quite some times. I can’t recommend them enough.”

“Had such an amazing time! It was a perfect sailing day and the boat is beautiful. Nate and Ken are great, and we all had so much fun the entire time. They made us feel incredibly safe throughout the entire process, which I appreciated as I had never been sailing before. Can’t wait until we can go back again!”

“I had an amazing experience with True Sailing Hamptons! Nate and Ken were incredibly helpful and laid-back, making the whole outing enjoyable. My friends and I took advantage of what felt like the last warm weekend of the year, and it was the perfect way to spend it and unwind. Plus, we had a blast taking amazing photos and having a little photoshoot on the boat! I highly recommend True Sailing Hamptons for anyone looking to try something new or just spend some relaxing time on the water. Can’t wait to sail with them again!”

“Had an amazing time on the true sailing yacht. My wife and baby as well as two friends met the captain at Sag Harbor Yacht Club and then sailed around the bay. We stopped at a little sandy beach where we went for a swim and relaxed listening to music. All around a great time!”

"I wanted a professional crew for a long weekend with my family, and True Sailing provided a skilled captain and a stewardess who made everything effortless. Best Espresso Martinis I have ever had. After the trip, the crew stayed and cleaned the interior and washed the deck. We didn’t have to move a finger. Thank you for this memorable weekend on our Beneteau."

“I’ve chartered a boat with Captain Nate several times over the years. This recent time was the best yet. We did a six hour sail around Shelter Island. The weather and wind was perfect, even went for a lovely swim when we stopped to moor off a secluded beach. Can’t beat it!”

“An incredible way to spend an afternoon! Nate showed us the best in sea shanties, harbor lore, racing prestige, and ol’ fashion sailing knowhow. Swing by the farmers market on your way to the harbor and enjoy all the local sights and flavors of this beautiful part of Long Island.”

“We had a great time! Nate, the owner, was awesome and super easy to coordinate with. He was flexible with us because of the weather. 10/10 would recommend!”

"Storing my boat for the winter used to be a headache. Having a Yacht Manager is such a game changer. True Sailing took care of the haul-out, winterization, and even coordinated a few maintenance tasks while the boat was in storage. Come spring, she was launched and ready to go without a single issue. Highly recommend!"

“I couldn't rate this place more highly!! Captain Nate is one of the most down to earth people I have ever met. My friends and I had never been to the area and we wanted our experience to be special despite being tourists. True Sailing delivers on all fronts. Nate was superbly professional, but beyond his professionalism he makes you feel like coming back just because of the atmosphere he curates. 10/10!!!”

“We did the brunch cruise to celebrate my bday. We had such a great time, we extended another extra hour. Very laid back captain Bruce and Melissa took such great care of us, refilled drinks the moment a glass was empty and made a delicious brunch. Can only recommend and want to do it again for another occasion. Thank you very much for making my bday so memorable.”

“I came here for a birthday sail and it was absolutely amazing! I was greeted the moment I walked onto the pier and from then on, we were all given such personalized attention and service. It was a beautiful day and we had unbelievable views. Thank you Nate and True Sailing for an unforgettable experience!”

“Awesome experience! Nate and his crew were great. They were attentive, fun, and laid back which made for a really nice atmosphere. The food was also very delicious. I would highly recommend this company and I look forward to sailing with them again!”

“Best. Day. Ever.

As a treat for my friend's last weekend in New York, I took him sailing and It couldn't have been more perfect. Capt. Nate was very fun and super knowledgeable about the city - he also put up with all of my annoying questions about boats and sailing :)

The boat was beautiful and extremely clean. We had an amazing time! THANKS NATE!!!”

“Great scenic, relaxing way to see NYC from a whole new perspective. Crew was competent and provided great service. Loved the whole experience of having our own private sail around the Statue of Liberty and the tip of Manhattan. Would also have stayed for a drink by the dock restaurant at the end of the sail if we had time.”

“My wife surprised me with the champagne brunch cruise for my birthday last weekend, with four of our friends. We enjoyed a delicious brunch on the water with the Statue of Liberty and the downtown Manhattan skyline as our backdrop. Captain Nate and 1st Mate Becca were super friendly and easy-going, and everyone had a great time. Thanks Nate for an awesome day!”

“The absolute best way to experience New York City in warm weather! I consider NYC a second home but have never had the opportunity to see it than when on a private charter. Love True Sailing NYC, truly top of the line personal private charter. Nate is an amazing and knowledgeable captain. Sailed with Nate twice already in the past three months, once in the evening and another in the day time.”

“We went sailing with our family to celebrate my wife’s 60th birthday. It went beyond our expectations. Captain Nate and his first mate were professional, personable and really made it a wonderful night. We did the dinner cruise. The food for dinner was very good. The service was excellent. We sailed between NY and Jersey watching the sun go down, and enjoyed watching the city light up. Was a memorable trip.”

“Amazing sail with the True Sailing team in Sag Harbor. It was a beautiful, very windy day and we felt totally comfortable the entire time and had a blast. Will be back!”

“We had a great experience sailing with Nate, and I really mean sailing. He knows his boat and the winds and is extremely attentive to the desires of his passengers. I highly recommend him.”

“Great tour company. Very intimate, very professional, very fun. We went sailing with Captain Nate who I would highly recommend. He’s a really cool guy. My 70 year old Mother and my 3 year old son both had an amazing time. Highly recommend it.”

“We went in a group for an afternoon sail and we had a blast! It was 6 of us and the captain with his crew. They provided drinks throughout the trip which were delicious. The trip was about 2 hours and you can lay all around the front of the boat which is clean and tidy. The bathroom was well kept and easy to use. The captain and crew were friendly and very helpful. We would definitely book again!!”

“The 2-hour cruise around lower Manhattan was amazing. Captain Nate is not only a great captain, he is also the kind of guy you can have a drink with afterwards. From the minute he meets you at the dock he is warm and inviting and you can tell he loves what he does and he wants you to love it, too.”

“Nate and his crew are super friendly, professional and knowledgeable! This is a great charter company, and it will be the highlight of your Hamptons trip!”

“Had an amazing experience with True Sailing. The boat was clean and comfortable, and the captain went out of his way to make sure we had everything we need. He was also a really fun guide and made sure everyone had a good time. Would definitely recommend it to anyone wanting to sail in the Hamptons and I’m looking forward to chartering with them again.”

“Nate and the cruise were outstanding. Our guests were extremely impressed by the boat and the service. We are return passengers and look forward to joining Nate again soon!!!”

“We had an excellent Sunday afternoon of sailing around Sag Harbor with True Sailing! It was very convenient getting on and off the boat, and Nate was incredibly knowledgeable about the local area. An altogether wonderful day made possible by a great captain and a great charter company.”