When it's time to trade in the South Beach scene for more secluded sand, hop onto US-1 South for a seaside, scenic three-hour drive to the historic southern most city in the contiguous US. The archipelago that runs from the mainland of the Florida peninsula varies between lush mangroves barely above sea level causeway making this drive one of the more entertaining legs of roadway. Surrounded by jewel-colored seas, finding a secluded vista is no challenge. We recommend stopping off at Kaiyo Grill in Islamorada—about halfway between Miami and Key West—for some of the best sushi and grilled seafood in the keys. A quiet, jungle-like setting makes dining in this relaxed roadside joint a great segue from the city to the relaxed vibe of the Keys. Carry on for another hour to Bahia Honda State Park for postcard-perfect beaches with white sand and a seemingly endless electric blue expanse. After arriving at Mile Marker Zero, it's time to ditch your shoes and slow down. History buffs will appreciate the the Ernest Hemingway Home & Museum in Old Town while everyone will appreciate one of America's most famous sunsets. Forget the "cheeseburger in paradise'" and opt for Blue Heaven's fresh seafood specials, especially when Yellowtail Snapper is in season. One look at Key West's quaint streets and sleepy vibe may turn this day trip into a long weekend.