Sail Kennebunkport with options to relax or take the helm
1.5 Hour Sail
Up to 12 people
Soda & water
See Kennebunkport from the water on a 1.5-hour sail with a local captain and crew. Sit back and relax or get hands-on as you enjoy sun and salt air.
Ages 5+ only. Gratuity is not required; typical charter boat gratuity is around 20% of the trip total.
Per person bookings: full refund if you cancel 3+ days before departure. Private charters: full refund with 5 days notice. If Pineapple Ketch cancels due to severe weather, mechanical failure, or safety issues, reschedule or get a full refund. No-shows are non-refundable.
Arrive to the boat 10–15 minutes before your scheduled departure time. The sail departs the dock promptly at the scheduled time.
Park at the Nonantum Resort; free parking is extended to all guests of the Pineapple.
Pack something to eat along with your favorite beverage. Soda and water are provided.
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.
This was a fantastic experience. Water was brutally cold (10/21/2025) but the feeling of stepping back into the hot sauna is like no other. I have access to a commercial gym sauna for free and paying for this experience felt totally worth the money. If you live in New England or are visiting ME I think this is a must do! Justin was easy going and totally psyched to facilitate our experience, Enjoy!
ewan Bennett
December 21, 2025
This was a fantastic experience. Water was brutally cold (10/21/2025) but the feeling of stepping back into the hot sauna is like no other. I have access to a commercial gym sauna for free and paying for this experience felt totally worth the money. If you live in New England or are visiting ME I think this is a must do! Justin was easy going and totally psyched to facilitate our experience, Enjoy!
ewan Bennett
December 21, 2025