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All listings in Long Island

Incredible sailboat rentals in Long Island, United States.

4.9(Average of 118 reviews in this area)
11 listings
Charter Sailboat Cruiser in Stamford, Connecticut
Sailing in Stamford · 6 guests

Charter Sailboat Cruiser in Stamford, Connecticut

5.0
Superowner
$170-195hour
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 2022
$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 2022
$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 2022
$37person
Escape Manhattan! Take the LIRR directly to this beautiful 36' Jeanneau!
Sailing in Oyster Bay · 6 guests

Escape Manhattan! Take the LIRR directly to this beautiful 36' Jeanneau!

New
$175-275hour
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
$199hour
25' Bayliner for rent in East Rockaway
Powerboats in Freeport · 7 guests

25' Bayliner for rent in East Rockaway

New
$113-150hour
Private Schooner in NY
Sailing in Queens · 6 guests

Private Schooner in NY

New
$1,500day

Sailing Reviews in Long Island

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

    Mark was a fantastic host. Our group ranged in age from 35 to 76, and he made us all feel comfortable and have a great time. His boat is awesome and he knew the best spots to explore around the bay. Thanks Captain!

  2. 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!

  3. JL
    Jon
    Sail from Norwalk, CT - $220/Hour - $37/Person

    Our family of 5 all enjoyed a beautiful sail with Mark. Lovely boat with comfortable seating for all. Mark was very flexible with booking a time that worked for us and a very pleasant and knowledgeable captain. Recommend!

  4. 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!

  5. 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!

  6. NS
    Nicholas
    Charter Sailboat Cruiser 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.