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All listings in Southampton

Great sailboat rentals near Southampton, New York.

Page 1 of 112 listings

42' Catalina Sailing Yacht in the Hamptons - 4 Hours
Sailing in Sag Harbor · 6 guests

42' Catalina Sailing Yacht in the Hamptons - 4 Hours

5.0
$325hour
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
A Luxuriously Appointed USCG Certified Trimaran Large and Small Groups
Sailing in Sag Harbor · 25 guests

A Luxuriously Appointed USCG Certified Trimaran Large and Small Groups

5.0
$600hour
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
41' Beautiful sailing catamaran, perfect for lounging, swimming, and sailing
Sailing in Sag Harbor · 6 guests

41' Beautiful sailing catamaran, perfect for lounging, swimming, and sailing

New
$600hour
Instant Book
A Fully Crewed Luxurious Schooner Perfect for Sails and Events 12 - 41 Guests
Sailing in Sag Harbor · 41 guests

A Fully Crewed Luxurious Schooner Perfect for Sails and Events 12 - 41 Guests

5.0
$1,250hour
42' Catalina Sailing Yacht in the Hamptons - 3 Hours
Events in Sag Harbor · 6 guests

42' Catalina Sailing Yacht in the Hamptons - 3 Hours

New
$350hour
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
Hobie One 12 ft Sailboat for rent in Sag Harbor
Sailing in Sag Harbor · 3 guests

Hobie One 12 ft Sailboat for rent in Sag Harbor

New
$99hour
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. Ilona

    Ilona

    42' Catalina Sailing Yacht in the Hamptons - 4 Hours

    We had a great day out on the water with Nate! He was very flexible with starting a bit later due to the weather and had great communication overall. He and his crew are very kind and professional. The boat is great and this is a must-do while you are in the Hamptons!

  2. JL

    Jessica

    42' Catalina Sailing Yacht in the Hamptons - 4 Hours

    Our trip with Nate was awesome. He is a great host and made our trip incredibly comfortable and fun. He took us on a great route - where we were able to swim in clear waters, and get a good view of surrounding areas. Highly recommend! Went way above our expectations!

  3. 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!

  4. Mayuri

    Mayuri

    A Fully Crewed Luxurious Schooner Perfect for Sails and Events 12 - 41 Guests

    If you are looking for an amazing time, do not hesitate booking the Luna! Toby and his staff take care of you every step of the way. The boat is well equipped with servingware, water, and ice for your event. Fun bean bags are plenty aboard. Our guests enjoyed the awning and swim spot on a hot day, as well. Just a fabulous experience from start to finish!

  5. CF

    Christian

    42' Catalina Sailing Yacht in the Hamptons - 4 Hours

    Had a fantastic time with Nate on his sailboat. Our group arrived late and he was able to keep us out for an additional hour. Very considerate and friendly, enjoyed hearing about his sailing adventures. Hope to be back!

  6. 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:)