Key West, Florida
“It’s the best place I’ve ever been, anytime, anywhere,” said Ernest Hemingway about Key West. Closer to Havana than Miami, the city is the southernmost point in the United States. Its historic Old Town is a pleasure to discover on foot with a host of admiration-worthy Victorian duplexes built with the spoils of the long-gone salvage industry. Mallory Square and the adjacent Sunset Pier are the places to be if you don’t want to miss the daily celebration of Key West’s write-home-about-it sunsets. And for fans of Hemingway, the author’s former home is a permanent fixture on the Floridian drive-to island. Occupy an afternoon touring the Hemingway Home & Museum, or have a Hemingway-inspired libation at one of Southernmost Beach Resort’s four bars.
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Mount Desert Island, Maine
Go on a scavenger hunt to spot bears, moose, coyotes, and bobcats at Acadia National Park, which is mostly located on Mount Desert Island, the largest island in Maine. You could spend days kayaking, climbing cliffs, biking, and hiking the park’s famous peaks (for a few months each year, Cadillac Mountain is the first place in the U.S. where the sun rises). When you get hungry, embrace lobster in all its forms in one of the island's coastal villages like Bar Harbor and Northeast Harbor, or embark on a delicious sunset lobster cruise.