Pineapple Ketch Sailing

Step aboard the Pineapple Ketch, a beautifully restored 38’ Downeaster Ketch, known for its distinctive tanbark sails and gleaming black hull. Often referred to as Kennebunkport’s own “Pirate Ship,” the Pineapple is ready to take you on an unforgettable sailing adventure along Southern Maine’s stunning coastline.

Looking for the perfect way to experience the coast? Start your day with a Morning Sail, a refreshing escape that offers stunning views of Maine’s rugged beauty, the perfect way to begin your day.

For those seeking a bit more excitement, the Afternoon Adventure provides a dynamic and spirited experience. Enjoy the thrill of sailing as you cruise along the coastline, soaking in the natural beauty that defines Southern Maine.

In search of a romantic setting? The Sunset Sail is ideal for couples or anyone looking to unwind with a favorite bottle of wine or craft beer. As day turns to evening, you'll be treated to a beautiful view that creates a magical backdrop for your sail.

Each sail aboard the Pineapple Ketch is more than just a boat ride—it’s a one-of-a-kind experience tailored to your sense of adventure. Whether you're seeking a peaceful morning escape, a lively afternoon, or a romantic evening, a trip aboard the Pineapple Ketch will be a highlight of your Kennebunkport visit.