Sail into the evening light along Kennebunkport’s rocky coast
1.5 Hours
Up to 12 people
Soda, water
Step aboard The Pineapple Ketch for a 1.5-hour evening sail from Kennebunkport, cruising out the Kennebunk River and along the rocky shoreline. Enjoy the soft light near sunset, plus complimentary soda and water onboard.
Minimum age is 5+. Gratuity is optional; typical charter boat gratuity is around 20% of the trip total.
Per person bookings: cancel 3+ days before departure 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 concerns; reschedule or full refund. No-shows are non-refundable.
Arrive at 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; they extend free parking to all Pineapple guests.
Soda and water are provided. You can also bring your own snacks or beverages to enjoy onboard.
95 Ocean Avenue Kennebunkport, Maine 04046
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