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True Sailing
Caribbean
Your Sailing adventure awaits
With itineraries and yachts all over the Caribbean we can take you on a vacation that you’ll never forget. White sand beaches, clear blue water, jungle clad mountains, delicious local cuisine and fruity frozen drinks are just the beginning. You’ll swim with brightly colored fish and explore ancient ruins before returning to the comforts of your own private yacht. Are you ready?
Fill in the form below and we will begin setting up your dream sailing vacation.
WHY TRUE SAILING
Sailing is our passion and we want to share it with as many people as possible. We offer 2 to 8 hour private sailing trips on several different sailboats in the New York Harbor and the Hamptons. Some of our boats take up to 6 passengers and others up to 30 passengers. We also offer weeklong private charters on luxury sailboats and catamarans for up to 10 passengers in the Caribbean.
We maintain a strong emphasis on service, sustainability, and safety. Our staff will attend to all of your needs and keep you safe as we sail as much as possible and run the engines as little as we can. Our motto: “always be sailing”
WHAT ARE PEOPLE SAYING ABOUT TRUE SAILING?
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 partner 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!
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!!!
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.
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.
We have chartered True Sailing multiple times and have always enjoyed our time on the water. Captain Nate is very accommodating and provides everything you need to enjoy a relaxing afternoon and sunset cruise. The Elizabeth is meticulously clean and a perfect size for a group of friends and family to escape on to the waters. Looking forward to our next outing.
“Captain Nates provides all the inputs for a stunning & memorable day out soiling in the Hamptons From the moment we met him, Nate was super welcoming & ensured we were always comfortable throughout out character on his beautiful sail boat. Highly recommend.”