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.
1 Hour | $30 Per Person
Looking for a quick, convenient way to see Kennenbunkport? Try our one-hour, affordable sailing trip, complete with all the top sites you want to see.
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.
The Pineapple Ketch
