The Best Sailboat Rentals Near South Portland

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

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!

★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!

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.