4 Spaces Available. Double Berth Starting at $990/pp.

Set sail from Rockland for an unforgettable adventure through Maine’s remote bays and coves. Hike on islands only accessible by boat, explore secluded beaches, spot seals, eagles, and other wildlife, and soak in stunning sunsets from a private dinghy cruise. Nights are spent anchored in scenic spots like Seal Bay or the Merchant Islands, with optional stops at local events like the Swan’s Island Music Festival. Cruise at your own pace—take the helm and trim the sails with guidance from the captain, perfect for brushing up on Sailing 101–104, or simply relax on deck and let the crew do the work. Adventure, nature, and breathtaking views at every turn—this is Maine sailing at its finest.