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All listings in Long Island

Incredible sailboat rentals in Long Island, United States.

Page 1 of 113 listings

Charter Sailboat Cruiser Motorsail Yacht, in Stamford, Connecticut
Sailing in Stamford · 6 guests

Charter Sailboat Cruiser Motorsail Yacht, in Stamford, Connecticut

5.0
Superowner
$37person
Sail from Norwalk, CT - $220/Hour - $37/Person
Sailing in Norwalk · 10 guests

Sail from Norwalk, CT - $220/Hour - $37/Person

4.6
Superowner
Best of 2023
$36person
Sail From Northport or Huntington, NY - $215/Hour - $36 Per Person
Sailing in Huntington · 6 guests

Sail From Northport or Huntington, NY - $215/Hour - $36 Per Person

5.0
Superowner
Best of 2023
$50person
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
$100person
Sailing Long Island Sound with Captain Steve
Sailing in Port Washington · 6 guests

Sailing Long Island Sound with Captain Steve

5.0
$199hour
Sail From Port Washington, NY - $219/Hour - $37/Person
Sailing in Port Washington · 6 guests

Sail From Port Washington, NY - $219/Hour - $37/Person

4.7
Superowner
Best of 2023
$37person
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!

New
$175-$275hour
ASA practice sailing exercizes
Tours in Bronx · 6 guests

ASA practice sailing exercizes

New
$95person
Sunset C&C Sailboat cruise outside of NYC: the beauty of Long Island!
Sailing in Bronx · 6 guests

Sunset C&C Sailboat cruise outside of NYC: the beauty of Long Island!

New
$95person
Sailing JOURNEY on the Sound
Sailing in Stamford · 6 guests

Sailing JOURNEY on the Sound

New
$262hour
Fun in the Sun with Manhattan skyline in the background
Sailing in Bronx · 6 guests

Fun in the Sun with Manhattan skyline in the background

New
$95person
Private Schooner in NY
Sailing in Queens · 6 guests

Private Schooner in NY

New
$1,500day
25' Bayliner for rent in East Rockaway
Powerboats in Freeport · 7 guests

25' Bayliner for rent in East Rockaway

New
$113-$150hour

Sailing Reviews in Long Island

  1. 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.

  2. BS

    Bonnie

    Charter Sailboat Cruiser Motorsail Yacht, in Stamford, Connecticut

    Marco is the perfect captain. Extremely knowledgeable about boats, navigates the waterways with great confidence, and truly loves what he does. The boat is very clean, maintained beautifully, and the day was perfect. I would definitely sail with Marco again. Great experience!

  3. DD

    Daniel

    Sail from Norwalk, CT - $220/Hour - $37/Person

    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!

  4. LB

    Lyndon

    Sail From Northport or Huntington, NY - $215/Hour - $36 Per Person

    Amazing day on the water! Mark was super responsive from the moment I booked all the way through to our charter. We had an absolute blast as a group of friends sailing, swimming, laughing, drinking, and Mark was vital to making it a memorable experience. Would highly recommend Mark and will use him again!

  5. PP

    PARNAZ

    Charter 38' Pearson Cruising Monohull In Mamaroneck, New York

    Captan Rick's boat trip was an incredible experience that I highly recommend ! The planning was flawless, offering a perfect blend of activities. Captan Rick excellent communication and warm demeanor made the journey even more enjoyable. This boat trip is a must-do for anyone looking for an unforgettable day on the water!

  6. KB

    Keisha

    Charter 38' Pearson Cruising Monohull In Mamaroneck, New York

    The boat is large enough to comfortably fit a group of 10. We learned some new terms and had a sailing lesson. Capt Rick is a great vibe and fits right in with the group from kids to adult, the experience was one of a kind. Boat is very well kept and has lots of lounging areas inside and outside.