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$100-$300
All listings in Long Island

Incredible sailboat rentals in Long Island, United States.

Page 1 of 15 listings

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 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
Sailing JOURNEY on the Sound
Sailing in Stamford · 6 guests

Sailing JOURNEY on the Sound

New
$262hour
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. 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!

  2. 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.

  3. DE

    Desireé

    Charter 38' Pearson Cruising Monohull In Mamaroneck, New York

    Captain Rick was excellent!!! He is a skilled and patient captain. We had so much fun on the trip. Lots of laughs and great conversations. This day could not get any better. The boat and amenities were as advertised. I will definitely book this trip again with Captain Rick!

  4. Brooke

    Brooke

    Charter 38' Pearson Cruising Monohull In Mamaroneck, New York

    Capt. Rick was so fun! His knowledge of sailing and expertise made him a wonderful guide. Plus he is so personable! You can tell he really enjoys the water and loves to share the joys of being on the water with his guests! The boat was great and well outfitted! Such a wonderful experience!! I highly recommend! The trip on Capt. Ricks boat was so memorable and special! It made my 40th birthday an event to remember!

  5. Denis

    Denis

    Charter 38' Pearson Cruising Monohull In Mamaroneck, New York

    Rick was amazing and his boat was perfect for a larger group. He offered us an amazing time and great hospitality. We shared many laughs and many great stories. I would recommend it for anyone and you could not pick a better host. The boat was capable of hosting a party of 8-10 comfortably with plenty of room to lounge and take in the sun. Super clean and super well kept. He also offers several great historic pieces about the area and don’t forget to ask him about the jacuzzi!!!

  6. AF

    ASHLEY

    Charter 38' Pearson Cruising Monohull In Mamaroneck, New York

    Rick was passionate about his love for the water and for the art of sailing, he answered the questions the kids had, he even answered mine. He was great with the kids, pirate flags and buried treasure had them engaged from the start. The boat was incredible, the ride was comfortable and Rick was warm and inviting. I highly recommend sailing with Rick.