Rockland, Maine Sailing Cruises

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 the A Morning in Maine crew for a sunset sail with an intimate live blues experience with blues guitarist Roger “Hurricane” Wilson on July 11. Departing from Middle Pier beside the Blues Festival, the cruise passes Rockland Breakwater Lighthouse (and, weather permitting, Owl’s Head Lighthouse). BYOB, with bottled water available. Wilson brings decades of touring experience and has performed with blues legends including B.B. King and Buddy Guy.

Step aboard the historic Sarah Mead for a small-group sailing adventure on Penobscot Bay. Help haul traditional and modern lobster traps under sail, dock to tour the Rockland Breakwater Lighthouse, then cruise past the iconic Owls Head Lighthouse before returning to port.

Step aboard the historic Sarah Mead for a small-group sailing adventure on Penobscot Bay. Help haul traditional and modern lobster traps under sail, visit the Rockland Breakwater Lighthouse when conditions allow, and cruise past the iconic Owls Head Lighthouse with scenic views of Monroe Island.

Step aboard our intimate sailing lobster-boat that offers close lighthouse views and traditional trap hauling for a small-group sailing adventure on Penobscot Bay. Help haul lobster traps under sail, admire iconic Maine lighthouses, and experience the region’s rich maritime heritage on an authentic, hands-on voyage.

Discover Maine’s maritime traditions through a unique partnership between A Morning in Maine and The Apprenticeshop. Sail Penobscot Bay with Captain Tyler before enjoying exclusive behind-the-scenes access to an active traditional boatbuilding workshop, where skilled craftspeople preserve centuries-old techniques.

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!

Hailed as “the largest annual gathering of traditional schooners in America,” join us this year where at least twenty schooners are expected to participate in the 46th Annual Great Schooner Race scheduled to take place on July 3rd, 2026 in Penobscot Bay.