The Pineapple Ketch

"There's no better way to see Kennebunkport."

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.

  • 2-Hour Sailing Trip

    Explore Kennebunkport from the water as you soak up the sun and ocean air. On this sailing trip, you'll experience Pineapple hospitality and take in local points of interest.
  • Sunset Sail

    Enjoy a sunset sail as daylight fades on another beautiful day in Kennebunkport. Your captain and crew will guide you along Maine's coastline as you explore the landscape, homes, and resorts.
  • 2 Days Only!

    Wine Sails with Erica Archer!

    Join Sommelier Erica Archer for a scenic Wine Sail. You're in for an incredible wine education experience as you sail through Maine’s beautiful Kennebunk River with scenic views of Kennebunkport and Walker's Point.
  • Join us for a Scenic Sail

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