Kennebunkport Sailing Trips

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

Enjoy an evening sail as daylight begins to fade on another beautiful day in Kennebunkport. Your captain and crew guide you along as you explore Maine’s coastline.

Enjoy Pineapple hospitality while you soak up the sun and salt air. You are welcome to help haul line, set sail or take a turn at the helm.

Any of our regularly scheduled sails on the calendar can be booked as a private charter as long as no other guests are already scheduled.

Discover the ultimate escape with our luxury floating sauna nestled on the Kennebunk River.