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All listings in Southampton

Browse Boat Rentals in the Hamptons.

Page 1 of 115 listings

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

5.0
$600hour
Instant Book
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
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
$850hour
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
$325hour
27ft Daysailer Boat Rental in Montauk
Sailing in Montauk · 6 guests

27ft Daysailer Boat Rental in Montauk

New
$400hour
Charter 36ft Sloop In Westbrook, Connecticut
Sailing in Westbrook · 6 guests

Charter 36ft Sloop In Westbrook, Connecticut

5.0
$145person
42' Catalina ailing Yacht - Two Hour Sailing Charter - Sunset Sail Available
Sailing in Sag Harbor · 6 guests

42' Catalina ailing Yacht - Two Hour Sailing Charter - Sunset Sail Available

New
$400hour
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
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

5.0
$300-$330hour
22ft Catalina Daysailer Boat Rental in Montauk, New York
Sailing in Montauk · 5 guests

22ft Catalina Daysailer Boat Rental in Montauk, New York

5.0
$125-$145hour
Modern Luxury Sailing in the Hamptons and beyond onboard 34ft Hanse Sailboat
Sailing in Sag Harbor · 6 guests

Modern Luxury Sailing in the Hamptons and beyond onboard 34ft Hanse Sailboat

New
$300-$375hour
42' Catalina Sailing Yacht in the Hamptons - 3 Hours
Sailing in Sag Harbor · 6 guests

42' Catalina Sailing Yacht in the Hamptons - 3 Hours

New
$350hour
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
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
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. MB

    Mark

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

    Extraordinary experience on a comfortable and beautiful catamaran, with an excellent itinerary from Sag Harbor to Shelter Island for lunch and back. Captain Brian was super professional as was first Mate Erin in implementing and serving our extensive wines and hors d’oeuvres. The vibe of the team was fun, efficient but still chill. I highly recommend this as one of my best summer experiences and I’ve been in here my whole life and I’m in the hospitality business as a boutique hotel owner.

  2. ML

    Margaux

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

    We had such a fabulous time on this beautiful boat. Our captain, JM, and the crew Liz and Andrew were so friendly and attentive and amazing with all the kids we had. It was a wonderful afternoon and we can’t wait to do it again!

  3. SB

    Scott

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

    What a day on the water! Our Group of 7 people had an awesome time Captain Brian & Erin. The Catamaran was huge! The sun deck and the interior were clean and full of amenities. The Sailing around Sag Harbor and Shelter Island was something that we will never forget.

  4. AR

    Ashley

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

    Eric was quick to answer all of my questions. The boat was clean and the listing felt accurate. It was a fun experience and I would book again.

  5. AV

    Anna

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

    Brian and Erin were both amazing. We had the best afternoon on their boat. Highly reccomend!

  6. EC

    Eirum

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

    Captain Brian was the best! We sailed around Shelter Island, had a great swim, and enjoyed every minute on the boat! Perfect trip thanks to his great skills and warm personality!