Sailing Adventures with Schooner Heritage in Rockland, Maine

Rockland, Maine offers a rugged coastal playground where the Atlantic’s ever-changing moods meet glimmering islands and historic lighthouses. At the heart of this seafaring culture is Schooner Heritage, a Rockland-based adventure company specializing in windjammer sail trips that immerse guests in the authentic hands-on experience of traditional schooner life. Their flagship vessel, the Heritage, is the largest and most comfortable in the Maine Windjammer Association fleet, a fact that draws repeat sailors and newcomers alike.

Schooner Heritage’s trips range from multi-day voyages through Penobscot Bay’s island-speckled waters to themed excursions like Murder Mystery Dinners, lobster feasts, and lively Lobsters, Sailing & Music events. Their signature sailing experiences encourage hands-on participation—guests trim sails, haul lines, and row ashore in dories under the guidance of professional captains and crew. This blend of activity and relaxation creates a unique rhythm: afternoons spent jumping off the ship’s side or watching iconic Maine sunsets, evenings filled with acoustic jam sessions and expertly prepared meals geared around fresh local seafood.

The schooner’s wood-burning galley turns out full-course meals praised by guests as rivaling top restaurants, with lobster featured prominently. This gastronomic highlight complements views of islands like Isle au Haut and North Haven, plus the chance to see historic lighthouses up close.

Sailing with Schooner Heritage is about more than a trip—it’s a communal adventure that builds connections with the sea, the crew, and fellow travelers. It stands out in Maine’s outdoor scene by blending physical engagement, authentic maritime culture, and pristine coastal scenery. Whether you’re chasing the fall foliage, the thrill of the Perseid Meteor Shower, or simply the soothing rhythm of sails against the wind, Schooner Heritage delivers an unforgettable gateway into Maine’s maritime wilderness.