Now booking for 2025 sailing season! Book now!
Browse our collection of stunning day trips from Kennebunkport, Maine aboard Pineapple Ketch, our beautiful sailing yacht. Our Kennebunkport sailing tours explore stunning sights including Goat Island Lighthouse, the stunning homes along Ocean Avenue and Walker’s Point.
Explore Kennebunkport from the water as you soak up the sun and ocean air. On our sailing trips in Kennebunkport, 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 boat tour as long as no other guests are already scheduled.
Discover the ultimate escape with our luxury floating sauna nestled on the Kennebunk River.