Sailing in Rockland, Maine

Your island adventure awaits! Maine has over 3,000 miles of coastline, and almost half of that is on islands only accessible by boat.

Join us and a science educator from our partners at Herring Gut Coastal Science Center in Port Clyde as we set sail to learn about the ecology of Penobscot Bay!

Join Captain Tyler Waterson and local blues musician James Harriman for a special sunset sail with a live acoustic blues set.

Purchase the perfect gift: a sailing adventure on Penobscot Bay. Gift Cards are automatically emailed to the recipient and can be redeemed for any of our sailing tours or merch!

Every summer since 1977, the Maine Windjammer Association has hosted the Great Schooner Race, providing an opportunity for captains, crews and passengers aboard traditional vessels from all over the Eastern