Sailing Adventures with Schooner Heritage in Rockland, Maine

Rockland, Maine, is a charming coastal town on the edge of Penobscot Bay, known for its rugged islands, pristine waterways, and rich maritime history. The Schooner Heritage offers a truly unique private sailing adventure here aboard their flagship vessel, the Heritage. This experience is far from a traditional cruise—it’s an immersive windjammer journey that lets adventurers become part of the ship’s operation while enjoying the natural beauty of the Maine coast.

The Heritage is the largest and most comfortable schooner in the Maine Windjammer Association fleet, featuring spacious cabins and a welcoming galley where guests savor freshly prepared meals, including local specialties like lobster from Lobster Island. Captains Ben and Sean, along with the skilled crew, bring professionalism and warm hospitality to every voyage. Guests find themselves engaged in authentic sailing activities such as trimming sails, rowing to shore, and raising anchors manually—a perfect blend of navigation education and hands-on adventure.

Sailing through the Penobscot Bay islands, travelers witness breathtaking views of granite cliffs, dense spruce forests, and sparkling ocean waters. The region’s islands offer secluded coves and opportunities for swimming or simply enjoying the sea air from the deck. This trip invites guests to unplug and reconnect both with nature and each other, creating memories alongside fellow adventurers and seasoned sailors alike.

What sets the Schooner Heritage apart is the combination of hands-on sailing, gourmet food cooked on the wood-burning stove, and the chance to become part of a supportive onboard community. This is an experience that appeals to those seeking a genuine, small-ship sailing adventure coupled with the rugged, coastal beauty of Maine. With numerous repeat visitors and heartfelt endorsements, the Heritage stands out as a premier outdoor recreation operator in the Rockland area and beyond.