White Barn Inn

Kennebunkport is sort of the quintessential New England hamlet—and the beaches of Maine, while not the best for swimming, are stunning in their own way. The award-winning restaurant here is located in a historic barn that’s been on the property since colonial days, and is staffed by old-school, tuxedoed waiters. During the day, you can explore the town or check out the surrounding area by bike or canoe. Ask the concierge to arrange for a picnic basket, which you can bring along for a beachside lunch near one of the area’s idyllic lighthouses. While summer is peak season in Maine, it’s pretty great in the fall too.