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.

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