Sailing Adventure with Schooner Heritage in Rockland, Maine

Experience an unforgettable sailing voyage aboard the Schooner Heritage, the largest and most comfortable traditional windjammer in the Maine Windjammer Association fleet. Located in Rockland, Maine, this privately chartered sailing adventure offers an authentic maritime experience where guests are encouraged to assist with sails, rowing, and daily shipboard tasks, connecting you directly with the sea and the historic craft of schooner sailing.

Rockland is a vibrant coastal town along Penobscot Bay, known for its rich maritime heritage, lobster fishing, and scenic islands dotted with granite shores and pine forests. The Schooner Heritage offers multi-day trips ranging from 3 to 6 nights, sailing through these stunning waters while providing exceptional culinary offerings prepared by one of the captains—an acclaimed chef who uses a wood-burning stove on board. Enjoy freshly caught lobster on Lobster Island and lively guitar jam sessions on deck after active days exploring the coastline and bays.

More than just a cruise, this is hands-on, immersive sailing where guests share meaningful moments raising sails, navigating anchor lines, and even jumping off the ship to swim in clear coastal waters. The crew, led by Captains Ben and Sean, create a warm, welcoming atmosphere fostering new friendships and a sense of community among adventurers. It’s an ideal choice for those seeking a balance of relaxation, adventure, and education within the unique ecosystem and culture of coastal Maine.

Sailing among the granite islands and sheltered bays, you’ll discover tranquil coves, rugged shorelines, and abundant wildlife including seals and eagles. The region’s history as a fishing and shipbuilding hub enriches the experience, allowing guests to connect with centuries-old maritime traditions. Whether you’re a first-timer or a returning guest, the Schooner Heritage offers a rare, soulful escape to the heart of Maine’s coastal wilderness.