The Best Sailboat Rentals Near Marblehead

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!

Cal 36 Sailboat Rental in Marblehead, Massachusetts

We had a great day on the water with Captain Alan. Highly recommend this charter. Captain Alan is a knowledgeable and affable sailor. The trip consisted of myself and my wife, our twenty two year old daughter, and her two friends; the boat was easily accommodated all of us, Captain Alan and his first mate. Highly recommend Marblehead and the North Shore area for convenient and scenic sailing. We were even able to swim off the boat. Great day!

Cal 36 Sailboat Rental in Marblehead, Massachusetts

Outstanding captain, flexible schedule, based on wind conditions. Knowledgeable captain, plan b to view the seals during calm wind conditions, that kept my grandsons (8,10) entertained. First mate Mable , very helpful, both with the boat and the boys.

Cal 36 Sailboat Rental in Marblehead, Massachusetts

My sisters and I had a wonderful experience with Captain Allan Waldman. We rented the Emma Rose to take our mother’s ashes and scatter them in the ocean out of Marblehead Harbor, where the boat is conveniently located. We were transported to and from the boat by independent launch from Commercial Street Wharf. The weather was luckily beautiful and the trip was made quite memorable by Captain Allan’s sensitivity to our needs. He is comfortable with people and gave us the time to absorb the experience we had and also enjoy the beauty of the afternoon.

Cal 36 Sailboat Rental in Marblehead, Massachusetts

I booked this trip to propose to my girlfriend and Allen made this very memorable. The harbor and surrounding area in Marblehead was beautiful, and seeing all the other sails in the horizon is a scene that makes this experience worth every penny. Allen was friendly and very knowledgeable. I had never been on a sailboat before but the classic look and close quarters seating area of this vessel made for a romantic setting. Absolutely recommend for a date, special occasion, or just a casual sail around the Gold Coast.

Sail with us aboard our 64’ sailing yacht Artemis. Gloucester MA. Meal included!

I booked a trip for my niece and nephew to scatter their mom's (my sister's) ashes. They were very pleased with the service, and it was a perfect day. Communication was fantastic, and the crew was very receptive to their needs. Don't hesitate to book with them!