The Best Sailboat Rentals Near Rockland

Martha’s Vineyard Private Sailing onboard 42ft Pearson Sailboat

Highly recommend if you’re looking for something different to do than what all the other tourists are doing when visiting Martha’s Vineyard, you might want to consider contacting Mason for a peaceful & relaxing sailboat ride to see the beautiful coastline of MV that most don’t get to experience while on land. We’ll definitely be back next year to do another trip

41' Beautiful sailing catamaran, perfect for lounging, swimming, and sailing

My girlfriends and I had the best time celebrating a bachelorette party with Captain Brian and his beautiful boat! From the very start Brian had quick communication and was helpful answering our questions. The actual boat was so nice, with a rustic charm. It comfortably fit all 10 girls. Brian made the day extra special - he’s so kind and fun. Would definitely recommend to this others and even hope to do another trip again!

42' Catalina Sailing Yacht in the Hamptons - For a perfect day on the water /)

Nate and Jaime were the absolute best from start to finish! Super great communication and excellent service - loved the swimming spot and how knowledgeable Nate was about the area and other boats. Exceeded our expectations, will definitely book with Nate again!

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!

42ft J Boat Sailing Yacht in Newport, Rhode Island

Anthony was kind enough to take us out on super short notice when a different boat canceled us. We were traveling for the sole purpose of an afternoon sail and had nonrefundable travel and hotel. i am so grateful the other boat canceled because Anthony and his J42 were simply the best! i recommend him highly to anyone who wants to sail. He appeals to all levels of sailors and has great knowledge of the area and is willing to share. We got some history lessons as well as the sail. Fantastic!

Sunfish Sailboat on Merrymeeting Lake in New Hampshire

Had a great day out on Matthew’s lovely sunfish. Matt was very communicative and also offered us an alternative activity in case of no wind. Thankfully, the wind filled and my mom and I had a great day of sailing on beautiful MerryMeeting Lake! Matt was very pleasant to talk with and answered all of our questions about the area and the boat. We will definitely be back and would encourage others to rent this boat from Matt!