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All listings in Stamford

Great sailboat rentals near Stamford, Connecticut.

Page 1 of 13 listings

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

Charter Sailboat Cruiser Motorsail Yacht, in Stamford, Connecticut

4.9
Superowner
Best of 2025
$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
Sailing JOURNEY on the Sound
Sailing in Stamford · 6 guests

Sailing JOURNEY on the Sound

New
$262/hour

Sailing Reviews in Stamford

  1. AB

    Ally

    Charter Sailboat Cruiser Motorsail Yacht, in Stamford, Connecticut

    We had the best time with Captain Marco!!! He was so kind, easy to work with, and had great communication. He was awesome!!

  2. 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!

  3. 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.

  4. 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!

  5. 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!

  6. AG

    Avirat

    Charter Sailboat Cruiser Motorsail Yacht, in Stamford, Connecticut

    Marco communicated clearly about the parking and dock to get to the boat. We left on time and he explained us about the boat, sails and we put up the front sail up together. It was amazing watching the sunset on the boat. 10/10 would recommend