The Best Sailboat Rentals Near Shelter Island Heights

Sunset Sail Buzzards Bay in a Classic Sloop!

I recently had the pleasure of sailing with Captain Freddie on his boat for a surprise two-hour cruise with my girlfriend, and it was an unforgettable experience. From the moment we stepped aboard, we were treated to breathtaking views of Buzzard's Bay and a sense of tranquility that only the open water can offer. The scenic beauty of the surroundings was truly stunning, and we found ourselves captivated by the serene atmosphere that only a sailboat can provide. Freddie was an absolute delight and contributed significantly to the enjoyment of our trip. His friendly and attentive personality put us at ease, and his passion for sailing was evident throughout the journey. He told us all about his restoration of his boat and made sure we were comfortable and well taken care of. We knew nothing about sailing, and he explained all about how the sails work, answered my endless questions, and his expertise and seamanship were evident. We felt completely safe under his guidance. The overall experience was nothing short of magical. From the sunshine and fresh air to laughing and relaxing on the deck while Freddie told us all about the area and his tales of trips to Martha's Vineyard and beyond. I scored some serious romance points with my lady by booking this trip. I would 100% sail with Captain Freddie again without hesitation.

43' Sailboat, Bristol RI & Beyond

We had a wonderful time with Catian Francis :) He is a lot of fun and makes you feel at home on his yacht. Things wemt very smooth and we can highly recommend having a exceptional sailing experience with him. Heiner

Spectacular Sailing in Newport, RI Aboard our 36' Catalina Sailing Yacht

Our sail with David was great! Even though we had light winds, we still covered a lot of ground. David is very capable and knowledgeable, and he also knows a lot about the area and the maritime region. The boat is in very good condition and very roomy. We ended up with 4 guests and were very comfortable. We expect to sail again with David in the future.

Come Sail & Party on Maybellene our well cared for 34' Beneteau Yacht

A beautiful evening that far exceeded our expectations. Dave was a fantastic captain and host giving us a relaxing and memorable experience on our sunset cruise. Bottle of wine, lovely snacks and the boat was pristine. Don’t think twice about adding this to your itinerary for a spectacular evening.

Sail From Northport or Huntington, NY - $200/Hour - $33.33/Per Person

Great trip Marc helped plan our trip Boat was exactly what we were told it would be All aspects went smooth great communication

The Only 40ft Hinckley Sailboat in NYC Harbor – Sail in Style!

We had an AMAZING experience! The boat was clean, comfortable, and offered fantastic views. We appreciated the smooth ride and the opportunity to take stunning photos of the Statue of Liberty up close. Highly recommend!!!