Skip to primary navigation Skip to content Skip to footer

The Pineapple Ketch

The Best Sailing Trips in Kennebunkport, Maine

Book a trip

Book Your Kennebunkport Experience

Book Your Kennebunkport Experience

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.

Join us on a 5-Star Sailing Trip!

The Captains were very informative on sailing and all the sights to be seen from the boat. They had interesting tales to tell as well. Very enjoyable & relaxing sail, could've spent all day out at sea!! I highly recommend taking the trip!!

Beckily70 | Tripadvisor

Justin and Captain Jim were fantastic guides, and gave us some history of the surrounding area, restaurant, recommendations, and houses that we saw on the cruise. We took the midday sailing cruise, and it was just beautiful to be on the Atlantic in good weather. I very much recommend this cruise.

Cindy C. | Tripadvisor

We had a wonderful sunset cruise in mid-October. Scenery was amazing and captain and crew were wonderful hosts. Highly recommend.

Megan A. | Tripadvisor

Nice sailboat. Comfortable seats. Friendly and informative crew. Great view of the estates along Ocean Drive. We had a beautiful day and a nice smooth ride. Strongly recommend.

Gregory I. | Tripadvisor