The Best Sailboat Rentals Near Edgartown

Charter 38' Pearson Cruising Monohull in Mamaroneck, New York

Had a GREAT day on the sound with Captain Rick. His boat is in excellent condition clean comfortable and so well maintained. Rick is a very experienced sailor with whom we always felt safe. He showed us all over Long Island Sound, which he knows so well. I highly recommend Rick for a great day on the water!!

Sail NYC's skyline aboard the Genesis, a beautiful classic sailboat!

We are still talking about our time aboard The Genesis! Eric was so welcoming to our family, ages 2 - 70! A true sailor, Eric took us on a two-hour sail from Chelsea Piers to the Statue of Liberty. He shared his endless knowledge about NYC as we passed spots of interest on the shoreline. Eric was super kind and patient with our 5-year-old grandson, allowing him to steer the boat. That experience was priceless. The Genesis is a wonderful sailboat that has been lovingly and meticulously cared for. Thank you, Eric, for helping us celebrate Nick's 70th birthday. It was perfect!

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

Our sail with David was wonderful! He’s so nice and had some great ideas for pictures for our engagement shoot!

Martha’s Vineyard Private Sailing onboard 42ft Pearson Sailboat

Capt. Mason and Capt. Lynne are ABSOLUTELY AWESOME. Their 42' sail boat was incredible and my party of 5 had a fantastic time on our charter. They are knowledgable, accommodating and true sailors through and through. My wife and I HIGHLY recommend Capt. Mason for any charter needs you may have, using his yacht or any other!

Martha’s Vineyard Private Sailing onboard 42ft Pearson Sailboat

Mason and Lynne were amazing captains on a private sail charter! So easy to communicate with throughout my planning process and amazing people overall! Had a great time being on the boat with them! Would absolutely recommend them and this experience!

Martha’s Vineyard Private Sailing onboard 42ft Pearson Sailboat

An afternoon on the water aboard the Our Passion is like an afternoon in paradise. The sailboat is gorgeous and comfortable, the skipper and crew more like instant old friends, and there’s no better place to sail than Martha’s Vineyard. An 11 out of 10 experience.