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All listings in Long Island

Incredible sailboat rentals in Long Island, United States.

Page 1 of 18 listings

Hunter Marine Passage 450 - Sail from Norwalk/Westport, CT
Sailing in Norwalk · 12 guests

Hunter Marine Passage 450 - Sail from Norwalk/Westport, CT

4.7
Superowner
$200/hour
Charter Sailboat Cruiser Motorsail Yacht, in Stamford, Connecticut
Tours in Stamford · 6 guests

Charter Sailboat Cruiser Motorsail Yacht, in Stamford, Connecticut

4.9
Superowner
$225+/hour
Sail From Northport or Huntington, NY
Sailing in Huntington · 12 guests

Sail From Northport or Huntington, NY

4.8
Superowner
$150/hour
Charter 38' Pearson Cruising Monohull in Mamaroneck, New York
Sailing in Mamaroneck · 10 guests

Charter 38' Pearson Cruising Monohull in Mamaroneck, New York

5.0
$50/hour
Sail Long Island's Gold Coast on this beautiful 36' Jeanneau!
Sailing in Oyster Bay · 6 guests

Sail Long Island's Gold Coast on this beautiful 36' Jeanneau!

5.0
$197+/hour
Sailing Long Island Sound with Captain Steve onboard 34ft Beneteau Oceanis
Sailing in Port Washington · 6 guests

Sailing Long Island Sound with Captain Steve onboard 34ft Beneteau Oceanis

5.0
$169+/hour
Limited Availability
30ft C&C 30 MK 1 Sailboat: Jersey City Harbor Sailing with Views of NYC Skyline
Sailing in Bronx · 6 guests

30ft C&C 30 MK 1 Sailboat: Jersey City Harbor Sailing with Views of NYC Skyline

New
$150/hour
Sailing JOURNEY on the Sound
Sailing in Stamford · 6 guests

Sailing JOURNEY on the Sound

New
$262/hour

Sailing Reviews in Long Island

  1. EC

    Erica

    Hunter Marine Passage 450 - Sail from Norwalk/Westport, CT

    Mark was absolutely fantastic! He was in great communication with me for the planning, was extremely flexible with the departure time given the weather forecast within the days before, and overall made it the best sailing experience possible! The boat was in incredible condition and surpassed what is even pictured. I couldn’t recommend him more and we will definitely be sailing with him again

  2. DD

    Daniel

    Hunter Marine Passage 450 - Sail from Norwalk/Westport, CT

    Booked Mark’s boat for a maternity photo shoot. Everything was perfect! He was very communicative and made the whole process very easy. He even came to pick us up from the beach. The boat is gorgeous and we had an amazing time. Would definitely recommend. Thanks Mark!

  3. NS

    Nicholas

    Charter Sailboat Cruiser Motorsail Yacht, in Stamford, Connecticut

    Marco was a wonderful captain and we had a great time watching fireworks from Todd's Point on the water. He piloted the ship safely and got us "front row seats" for the show. He also was mindful of other boaters in the area and got us out before the show ended so we weren't stuck or in danger. This was a surprise for my partner and Marco made it so worth the wait to reveal that we were going on an adventure in this beautifully renovated, fully equipped and well maintained ship. Would do this trip over 100 times! I highly recommend Marco for anyone that wants a safe, comfortable, and truly special time on the water.

  4. NT

    Nick

    Sail From Northport or Huntington, NY

    Mark is a wonderful captain and person all around. He is very communicative and informative both before and while we were on his sailboat. We had the best time sailing from Huntington to Northport. He sang a Happy Birthday to our Mom and brought out his guitar! Thanks so much, Captain Mark!

  5. CH

    Cynthia

    Sail From Northport or Huntington, NY

    We had the absolute best day celebrating my birthday thanks to Captain Mark! From the moment we stepped on board, he made sure every detail was perfect. He had snacks and drinks ready for us, made sure everyone was comfortable, and truly went above and beyond to make the day special. He was so friendly and easygoing — he got along with everyone effortlessly and made us all feel welcome. One of the most memorable moments was when he pulled out his guitar and sang me “Happy Birthday.” It was such a thoughtful, personal touch that made the day feel even more magical. Throughout the entire experience, Mark paid incredible attention to detail, always checking in to make sure we were having a great time and had everything we needed. He was a great communicator leading up to the day, extremely accommodating to all of our requests, and even followed up after to make sure everything went smoothly. He also made safety a priority and got us back to shore safe and sound without a hitch. Captain Mark is not only a fantastic captain but a genuinely kind and thoughtful person. I couldn’t have asked for a better birthday or a better host. Highly, highly recommend!

  6. Aden

    Aden

    Sail From Northport or Huntington, NY

    Mark was super cool, and we had a great time overall. The only issue was that the zodiac boat at the front was blocking access to the bow, so we couldn’t use that part of the boat. We also wanted to swim, but there was probably a miscommunication — we ended up eating during the time we should’ve been swimming, and later Mark said it was too late. That was a bit disappointing, as we didn’t get to swim at all during our 4-hour trip. Everything felt safe and nice overall. Mark let us play any music we wanted, and everything was clean. A longer trip with more time would definitely be a better option next time.