Classic Sail Boston

My wife arranged a 2 hour sail with Classic Sail for my birthday. It was a really great time. The captain (David) was friendly, casual, and informative, and let me have a hands on experience. The Captiva is a Chesapeake Skipjack. When the wind got up a bit the captain got us moving quickly and got the boat really leaning. It's a fun and memorable experience. Highly recommended!

Captain David is a true gem! He made our experience so fun and relaxing. The sail boat is so charming and runs close to the water so you can stick your feet in, which is nice on hot days. We LOVED our charter and 10/10 recommend. We plan on going again soon.

David is amazing. Our charter was a blast and a great way to celebrate our first anniversary! David was kind. His boat, The Captiva, is gorgeous. He clearly puts his heart and soul into the boat and trips. There is not a better way to enjoy some time on the water and beautiful views of Boston. Our only wish was that we had booked the longer charter!

Captain David is the best!! So sweet, funny, professional and hilarious. Takes great pics. It was a great time and we all felt safe and cared for during the corona virus. Highly recommend!!!

Our day sailing Boston Harbor last summer with Classic Sail was wonderful. The boat itself is beautiful and unique, and we couldn't have been happier with David as Captain. He was charming, knowledgeable, and kept our 2 young boys feeling safe and happy the whole time. We came out of this experience with a new love for sailing and for Boston. We will certainly be back.