The Pineapple Ketch
The Best Sailing Trips in Kennebunkport
Our Sailing Trips
Most Popular! | 2 Hours | $45 Per Person
Explore Kennebunkport from the water as you soak up the sun and ocean air. On this trip, you experience Pineapple hospitality and see local points of interest.
2 Hours | $45 Per Person
Enjoy a sunset sail as daylight fades on another beautiful day in Kennebunkport. Your captain and crew guide you along Maine’s coastline, as you explore the landscape, homes, and resorts.
We Also Offer Private Charters!
About Us
Set sail aboard the Pineapple Ketch, a lovingly restored 38’ Downeaster Ketch. With distinctive tanbark sails and a shiny black hull, the Pineapple paints a familiar sight on the Kennebunkport horizon — many refer to it as the Port’s “Pirate Ship.”
The Pineapple offers several options to get you out exploring Southern Maine’s beautiful, rocky coast. For a scenic cruise, choose a morning sail when the skies are clear and the seas are calm. If you prefer a more active sail, we recommend an afternoon trip when the winds are up. Romantics can head out for a sunset sail in the salty air with a favorite bottle of wine or craft beer.
No matter which option fits your tastes, a sail aboard the Pineapple Ketch is sure to be a Kennebunkport highlight.
