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All listings in Long Island

Incredible sailboat rentals in Long Island, United States.

Page 1 of 17 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
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
Limited Availability
Sail From Northport or Huntington, NY
Sailing in Huntington · 12 guests

Sail From Northport or Huntington, NY

4.8
Superowner
$150/hour
Limited Availability
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
$225+/hour
Instant Book
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 Reviews in Long Island

  1. JP

    Jenny

    Charter 38' Pearson Cruising Monohull in Mamaroneck, New York

    I can’t say enough about how great this experience was! I celebrated my birthday, and it will definitely be one of the most memorable ones. The boat was beautiful, clean, and spacious. The best part was having Captain Rick on board. He was knowledgeable, kind, and made us feel very comfortable the entire time. He showed us around, shared interesting information, and made sure we had a smooth and relaxing sailing trip. Truly an unforgettable experience!

  2. AM

    Anna

    Charter Sailboat Cruiser Motorsail Yacht, in Stamford, Connecticut

    We had a wonderful experience on the water with Captain Marco. He was incredibly friendly, knowledgeable, and made our family feel welcome from the moment we stepped aboard. Our children had a fantastic time, and Marco did a great job engaging with them and making the experience memorable. It was the perfect way to celebrate a special occasion as a family. Highly recommend!

  3. PC

    Peter

    Charter 38' Pearson Cruising Monohull in Mamaroneck, New York

    Had a GREAT day on the sound with Captain Rick. His boat is in excellent condition clean comfortable and so well maintained. Rick is a very experienced sailor with whom we always felt safe. He showed us all over Long Island Sound, which he knows so well. I highly recommend Rick for a great day on the water!!

  4. Laura

    Laura

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

    I would highly recommend sailing with Captain Steve! He is extremely knowledgeable and an excellent sailor. We loved our sail with him!

  5. KG

    KJ

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

    Jonathan is very knowledgeable of the area and a great captain. Will definitely book with him again!

  6. jj

    joy

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

    stellar experience overall, great memories with my family and learned a little history about oyster Bay.