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.

Summer Sailing at its Best!

"I love the smallness of the Pineapple Ketch because the fewer number of sailors makes for a more intimate sailing experience. Sailing off the coast of Kennebunkport is always a treat because you get to see many of the large "Summer Cottages" as well as the President Bush compound from the water!"
-Rick L. on TripAdvisor

Relaxing Trip!

"Enjoyed a cruise on the Pineapple Ketch on my birthday. It was the perfect way to spend a relaxing two hours. The captain and crew were very friendly and helpful. We saw the coastline from a whole new point of view. It was beautiful."
-Jennicon on TripAdvisor

Extremely Enjoyable!

"We had such a nice time on the after-lunch 2-hour cruise piloted by Captain Dan and Crew-woman Isabelle. This was our first time on a sailboat, and they made it so easy for us. Perfect weather, about a dozen total passengers, ice-cold soda to enjoy with our brought-aboard snacks...We will definitely take this cruise again."
-Seth H. on TripAdvisor