The Best Sailboat Rentals in Gloucester

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.

Cal 36 Sailboat Rental in Marblehead, Massachusetts

Awesome experience & an amazing captain. The trip was relaxing and fun. Allan is super experienced, kind, and knowledgeable. He managed to smoothly sail through a sailboat race, without interfering with the race and showed us cute seals and beautiful mansions !!

Cal 36 Sailboat Rental in Marblehead, Massachusetts

We had a wonderful experience with Captain Allan and his beautiful sailboat! He was very nice and explained things to us, let us help him with the rigging and sailing, let us take pics and hang out all over the boat, let us play our music and bring our own cooler. We had fantastic weather and saw how beautiful Marblehead was! Would highly recommend!

Cal 36 Sailboat Rental in Marblehead, Massachusetts

Sailing with Captain Al was a wonderful experience. The entire Marblehead area was so beautiful to see from the water and Captain Al was a very informative guide. The sailboat, Emma Rose, was so picturesque, it really felt like we were in a movie. This is certainly an experience we will remember for a lifetime.

Cal 36 Sailboat Rental in Marblehead, Massachusetts

Captain Allen is an amazing captain great with kids and adults alike. Loved sailing with him and his stories were incredible. He taught me much about sailing the ship I feel I can almost sail myself with a small crew. Also fell in love with his 1967 sailboat I need one in my life! I could do this every day and I just might do that. He made our send off of out Father one of the best days we could have ever asked for. It really was the perfect day! Hope to see u soon onour next adventure. First m8 Phil out! 🤙☮️♥️