The Best Sailboat Rentals Near Boothbay

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!

★Midcoast Maine aboard the Schooner Yacht Meteor ★

We just got back from a wonderful day on the water :) We bareboat chartered the Meteor. Captain Neal was able to be flexible on our timing since our original day was bad weather and he did not have many bookings around the same time. He made perfect suggestions regarding weather, currents, tides and routes to help us learn the area quickly and be able to navigate a beautiful day on Penobscot Bay. 100% we will be back again! Treat his boat well and Capt Neal will treat you well in return! Thanks so much for a wonderful day!

Acadia/Mount Desert Island Sail onboard the classic 46-foot sailing ketch

Shana, Thank you and Nicholas for a wonderful experience on Saturday. Your communication was so helpful each time you texted especially with regard to weather and moving up the sail. We ladies had a fabulous private time on your boat and would absolutely do it again if the opportunity arises.

Sailing Adventure Aboard 44' Hunter Sailboat

I cannot rave more about how AMAZING our experience was with Geoff! 1000 stars! It was absolutely beautiful and he made sure we had the best view of the sunset. We booked with him for an engagement photoshoot and he was super professional, fun, and incredibly helpful throughout helping us get the perfect shots. I’d recommend booking with Geoff for any occasion. I will definitely book again! Thanks Geoff!

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!

Sunfish Sailboat on Merrymeeting Lake in New Hampshire

We had a fantastic experience renting Matt’s sunfish sailboat. He was easy to communicate with, gave excellent instructions, and the boat and lake were an absolute dream. He even pointed us towards a great local spot for ice cream/light bites after the sail. We will definitely be back to rent from Matt again!