Step aboard the Pineapple Ketch, Kennebunkport’s signature black-hulled ketch with rust-red sails that locals fondly call the pirate ship. Built in 1976 and lovingly restored, this 38-foot classic is Coast Guard–inspected yet inti...
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.
We had amazing sailing trip experience with Pineapple Ketch! The weather was windy in our favor and sunset colors were really beautiful! Thanks to the crew, Justin and Josh, for making it both fun and safe!
Vlady Polivtseva
October 7, 2025
We had amazing sailing trip experience with Pineapple Ketch! The weather was windy in our favor and sunset colors were really beautiful! Thanks to the crew, Justin and Josh, for making it both fun and safe!
Vlady Polivtseva
October 7, 2025