Miami

A day trip down the Overseas Highway to Key West offers the sort of absurdly scenic drive that makes you suspicious you're starring in your own indie film-turquoise waters on both sides, pelicans dive-bombing for snacks, and clusters of pastel beach houses straight out of a Jimmy Buffett hallucination. Originally strung together in the 1930s atop railway ruins destroyed by a hurricane (a classic Florida origin story), this 113-mile marvel sweeps you down through tiny postcard towns toward the famously irreverent streets of Key West, a place known equally for Hemingway's literary benders and the resident chickens strutting around as if they own the joint (spoiler alert: they do). Depart Miami or Fort Lauderdale bright and early-say, 7am, unless traffic jams and baked asphalt are your happy place-and budget at least three hours on the road, plus ample extra time for photo ops, snack stops, and philosophical discussions with resident iguanas. Stash away a swimsuit, generous sunscreen, comfy sandals, and enough cash ($100−$150 per person should cover your Havana-esque lunch, potent mojitos, and suitably eccentric souvenirs). Sure, it's touristy, sweaty, and occasionally overpriced-but the sublime sunset at Mallory Square, spontaneous encounters with pirate look-alikes, and bragging rights from conquering mile marker zero ensure this escapade will linger in your memory, and your stories, long after the sunburn has faded.