Kennebunkport

Every summer, bluebloods and preppies flock to Kennebunk and Kennebunkport’s shores—including the Bush family, which keeps its summer compound on Ocean Avenue. (Rest assured, you’re bound to feel comfortable in these parts whatever your political leanings; the 2004 election saw just as many Kerry/Edwards as Bush/Cheney bumper stickers around town.)

Politics plays even less a part in Kennebunkport’s most sought-after pursuits—namely shopping [1], dining [2], and sailing [3]. The town’s centrally located Dock Square is filled with crafts and clothing boutiques, cafés and al fresco patios. Burn off the calories at any of the town’s lovely parks and beaches, golf courses and boat outings.

And there are plenty of places to witness the town’s history in architectural form: old homes—from colonial and Federal to Greek Revival and Italianate in style—all overseen by the very active Kennebunkport Historical Society.