The Best Sailboat Rentals in Sag Harbor

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.

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.

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!

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!

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!

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!