We use cookies to improve your browsing experience.

And dolphins make us happy. Find out more about our cookies policy here.

All listings in Sag Harbor

Great sailboat rentals near Sag Harbor, New York.

5.0(Average of 19 reviews in this area)
10 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
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
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
Casa Sul Mare - Home on the sea
Events in Sag Harbor · 12 guests

Casa Sul Mare - Home on the sea

5.0
$1,250hour
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
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
A Luxuriously Appointed Schooner Perfect for Casual Sails and Events  up to 41
Sailing in Sag Harbor · 41 guests

A Luxuriously Appointed Schooner Perfect for Casual Sails and Events up to 41

5.0
$1,200hour
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
40' Beautiful sailing catamaran, perfect for lounging, swimming, and sailing
Sailing in Sag Harbor · 6 guests

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

New
$600hour

Sailing Reviews in Sag Harbor

  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 Luxuriously Appointed Schooner Perfect for Casual Sails and Events up to 41

    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. JL
    Jaina
    A Luxuriously Appointed Schooner Perfect for Casual Sails and Events up to 41

    We had the best time with Captain Toby. The boat was absolutely beautiful, and the staff was very attentive. We loved getting to cruise with this awesome team. It was the highlight of our weekend!