The Best Sailboat Rentals Near Chester

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.

Newport RI: Private sailing, sighting-seeing and swimming with Capt Eric

Eric and his boat were outstanding! This was a highlight of our Newport vacation. My family (wife, daughters in their 20s) went sailing for 3-4 hours. Eric pointed out lots of famous sites and told us the history of Newport harbor. He let my daughter sail most of time (she's an experienced sailor). I highly recommend Eric!

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!!!

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.