Castine

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It’s hard to imagine a more perfect seaside town than tiny historic Castine. Despite its isolation (by land), the village is a favorite destination for day-sailers from around the Maine Coast, and the presence of the Maine Maritime Academy ensures a regular influx of cosmopolitan students from around the globe.

Named after a French nobleman who married a local Native American woman and ran the town in the late 1600s, Castine values its history as a prize fought over by French, Dutch, British, and American seamen throughout the colonial period. After things settled down in the 1800s, it used its deep-water harbor and active East India trade to become the second-richest port in the country.

Today its waterfront downtown is a mix of historic buildings, grand captain’s houses, and swanky restaurants and galleries catering to the yachting set.

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