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$100-$300
All listings in Southampton

Great sailboat rentals near Southampton, New York.

Page 1 of 16 listings

Classic Beauty: Nautor Swan 46 Bluewater Cruiser, Sag Harbor, New York
Sailing in Sag Harbor · 6 guests

Classic Beauty: Nautor Swan 46 Bluewater Cruiser, Sag Harbor, New York

5.0
$300hour
Charter 36ft Sloop In Westbrook, Connecticut
Sailing in Westbrook · 6 guests

Charter 36ft Sloop In Westbrook, Connecticut

5.0
$145person
Hunter 170 Sailboat with Honda motor in Sag Harbor, New York
Sailing in Sag Harbor · 6 guests

Hunter 170 Sailboat with Honda motor in Sag Harbor, New York

New
$129hour
Sail on a classy and fast Sailing Yacht in the Hamptons, New York
Sailing in East Hampton · 6 guests

Sail on a classy and fast Sailing Yacht in the Hamptons, New York

New
$300hour
22ft Catalina Daysailer Boat Rental in Montauk, New York
Sailing in Montauk · 5 guests

22ft Catalina Daysailer Boat Rental in Montauk, New York

New
$125-$145hour
40' Sailing Catamaran for charter in Montauk
Sailing in Montauk · 8 guests

40' Sailing Catamaran for charter in Montauk

New
$300hour

Sailing Reviews in Southampton

  1. Maria

    Maria

    Classic Beauty: Nautor Swan 46 Bluewater Cruiser, Sag Harbor, New York

    Everything was top notch, Alan was very considerable and did everything to make this trip as pleasant for us as possible. The vessel is amazing and the experience was outstanding. I traveled with my two children (3&5) and it worked out really well. Highly recommend!

  2. HE

    Holly

    Charter 36ft Sloop In Westbrook, Connecticut

    Our first sailing experience was memorable and joyful thanks to Captain Joy! We enjoyed learning about the skills needed to interpret wind and water conditions and seeing the nesting snowy egrets:)

  3. MD

    Miranda

    Classic Beauty: Nautor Swan 46 Bluewater Cruiser, Sag Harbor, New York

    Had a great time with Captain Alan! Very comfortable ride, and great communication prior to departure. An excellent choice if you are looking for a sailing trip around Sag Harbor!

  4. Paul

    Paul

    Charter 36ft Sloop In Westbrook, Connecticut

    Captain Joy is an outstanding captain and we really enjoyed sailing with her on her beautiful sailboat on the Long Island Sound! We would definitely hang with Captain Joy again!!

  5. Remington

    Remington

    Charter 36ft Sloop In Westbrook, Connecticut

    Great time and great crew... look forward to seeing them again!

  6. Maksim

    Maksim

    Charter 36ft Sloop In Westbrook, Connecticut

    We had a great time sailing with Joy!