On the Waterfront Down east Maine is dotted with private islands—Oar, Clapboard, Chanterelle—where couples can play Yankee castaways. One of our favorites is the four-acre Spectacle Island, a short boat ride from Bar Harbor. The best time to go is June to September. Book Spectacle Island Estate, a three-bedroom cottage on this spruce-covered spot in Frenchman Bay, well ahead of time. The master suite has spectacular sea views, a four-poster bed, and a whirlpool. The wood-burning fireplace in the living room is cozy on foggy nights, while the wraparound porch makes for good afternoon bird-watching, when gulls and osprey swoop along the shoreline. Acadia National Park on Mount Desert Island offers rugged hiking trails (or walk along the beach and watch the lobster boats). The island rental also includes a seaworthy 27-foot powerboat manned by a licensed captain. Catch the boat back to Bar Harbor and have a seafood cioppino with fresh-caught fish or jumbo baked lobsters at La Bella Vita, in the Harborside Hotel.