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All listings in Long Island

Incredible sailboat rentals in Long Island, United States.

Page 1 of 17 listings

Sail From Northport or Huntington, NY
Sailing in Huntington · 12 guests

Sail From Northport or Huntington, NY

4.9
Superowner
$150/hour
Hunter Marine Passage 450 - Sail from Norwalk/Westport, CT
Sailing in Westport · 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 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
Sail From Port Washington, NY with Hunter Passage 456 Sailing Yacht
Sailing in Port Washington · 12 guests

Sail From Port Washington, NY with Hunter Passage 456 Sailing Yacht

4.8
Superowner
$219/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

Sailing Reviews in Long Island

  1. MC

    Mia

    Sail From Northport or Huntington, NY

    Captain Mark hosted us for my boyfriend’s surprise birthday party. Mark was extremely easy to plan with, accommodatingly sailed out of a more convenient port for us, and took us to two swim spots! The day was described as “the best outing ever” by many of our friends.

  2. AJ

    Aaron

    Sail From Northport or Huntington, NY

    Great captain, great experience. First time sailing for me and felt as comfortable as ever. Seamlessly kept me informed on the goings on with sailing so I felt at peace knowing what was happening. The boat was comfortable and safe. Captain mark was accommodating and friendly, good heart, good vibes! You'd be lucky to Have Captain Mark!

  3. LT

    Louis

    Charter Sailboat Cruiser Motorsail Yacht, in Stamford, Connecticut

    We had a great cruise on the sound. Marco was very personable and made sure everyone was comfortable and safe. I would highly recommend his boat. It is very well maintained and in excellent condition.

  4. JS

    Jimmy

    Charter Sailboat Cruiser Motorsail Yacht, in Stamford, Connecticut

    Marco is amazing and does a great job keeping us entertained in great conversations and education. TY Marco for a great team event!

  5. CF

    Carlos

    Charter Sailboat Cruiser Motorsail Yacht, in Stamford, Connecticut

    Captain Marco was absolutely amazing! He was incredibly attentive to our entire group throughout our birthday party celebration and truly went above and beyond. His energy and hospitality made it such a special and memorable day for all of us. We would definitely recommend him to anyone looking for a perfect day on the water and we are already planning our future boat adventures with him!

  6. Jon

    Jon

    Charter Sailboat Cruiser Motorsail Yacht, in Stamford, Connecticut

    Marco was a gracious host. The boat is beautiful, clean, and in great shape. We had a fantastic day on the water. I highly recommend!