The Best Sailboat Rentals Near ホールダーネス

Sunset Sail Buzzards Bay in a Classic Sloop!

I recently had the pleasure of sailing with Captain Freddie on his boat for a surprise two-hour cruise with my girlfriend, and it was an unforgettable experience. From the moment we stepped aboard, we were treated to breathtaking views of Buzzard's Bay and a sense of tranquility that only the open water can offer. The scenic beauty of the surroundings was truly stunning, and we found ourselves captivated by the serene atmosphere that only a sailboat can provide. Freddie was an absolute delight and contributed significantly to the enjoyment of our trip. His friendly and attentive personality put us at ease, and his passion for sailing was evident throughout the journey. He told us all about his restoration of his boat and made sure we were comfortable and well taken care of. We knew nothing about sailing, and he explained all about how the sails work, answered my endless questions, and his expertise and seamanship were evident. We felt completely safe under his guidance. The overall experience was nothing short of magical. From the sunshine and fresh air to laughing and relaxing on the deck while Freddie told us all about the area and his tales of trips to Martha's Vineyard and beyond. I scored some serious romance points with my lady by booking this trip. I would 100% sail with Captain Freddie again without hesitation.

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!

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!

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!

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

2nd sail w/ Rick & Deb. They are warm and entertaining hosts and their boat is a beauty. Wonderful sail last night and we were lucky to catch some wind and get up to 8 knots. A delicious charcuterie board was included. Highly recommend sailing the Artemis with Rick & Deb.

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

Rick and Deb create an unmatched experience. Once someone experiences 64’ and multiple sails propelling one through the water…. The comforts, viewing and lounging locations onboard…and the company/conversation with the captain/first mate (Rick and Deb). Anyone will consider this one of the greatest values and investments in experience they have made in a long time. Highly recommend.