Sail Kennebunkport at midday with a local captain, public or private
1.5 Hour Sail
Up to 12 people
Soda, water
See Kennebunkport from the water on a 1.5-hour midday sail with a local captain and crew. Relax in the sun and salt air, or get involved with sailing as you go.
Ages 5+.
Gratuity is appreciated but not required; typical charter boat gratuity is around 20% of the trip total.
Per person bookings: cancel 3+ days prior for a full refund. Private charters: 5 days’ notice for a full refund. Operator may cancel due to severe weather, mechanical failure, or other safety-related circumstances; reschedule or full refund offered. No-shows are non-refundable.
Yes. Pack something to eat and bring your favorite beverage. Soda and water are provided.
Yes. You can help haul line, set sail, or take a turn at the helm if you’d like, or you can sit back and relax.
Yes. Park at the Nonantum Resort; they extend free parking to guests of the Pineapple.
With an exceptional reputation among recent visitors, this Maine sailing operation clearly knows how to create memorable experiences on the water. Captain Justin, Josh, Charlie, and Jim get enthusiastic praise for being friendly, knowledgeable, and professional throughout trips. The crew shares fascinating local history and landmarks around Kennebunkport, adding educational value to the beautiful scenery. Guests appreciate that you can bring your own beverages and snacks while enjoying peaceful sunset sails or morning cruises along the coast. The boat itself earns consistent compliments for being clean, spacious, and well-maintained, with plenty of room even for larger groups. Multiple reviewers mention feeling safe and comfortable, even nervous first-timers who requested life jackets. The relaxed, personable approach from the crew keeps everyone laughing and learning throughout the journey. One interesting bonus: they also offer a floating sauna experience with cold plunging for those seeking something different. It's a genuinely excellent choice for getting out on the water around Kennebunk.
Great crew, great day, greal sail! Thank you.
Christopher Gilbert
July 6, 2026
Great crew, great day, greal sail! Thank you.
Christopher Gilbert
July 6, 2026
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