Jacksonville

Slipping off the shore of Little Talbot Island in a kayak feels a bit like sneaking backstage at Mother Nature's own arena-just you, the whispering tides, and maybe some judgy-looking herons wondering if you'll tip over. Set your alarm painfully early (yes, the sunrise is irritatingly beautiful), and get on the water before the crowds and Florida's relentless sun converge. Paddling through the pristine salt marshes, you'll feel like an intrepid explorer from centuries past-minus dysentery and scurvy-as you glide past oyster beds, sea turtles, and the occasional unimpressed dolphin. Secure your kayak rental or tour about a week ahead, bring along sunscreen, bug spray, and snacks (because hangry adventurers are the worst), and expect to shell out around $40-$60 for a memorable couple hours. Sure, you might end up damp, sunburnt, and with suspicious tan lines, but the bragging rights of casually mentioning you paddled through northeastern Florida's primeval wilderness make every awkward splash and mosquito bite deliciously worth it.

St. Augustine isn't just old-it's properly ancient in the American sense, clocking in at over 450 years, predating colonies and revolutions, and still delightfully flaunting its wrinkles. An overnight trip here is your chance to swagger through cobbled streets where conquistadors once staggered, arguing with bartenders over rum tabs. Plan to arrive late morning, after tourists have had their pancakes, but before afternoon nap-inducers set in, leaving you prime hours to explore quirky downtown boutiques and dodge horse-drawn carriages manned by suspiciously cheerful tour guides. Bring comfortable shoes for the uneven brick roads and sunscreen strong enough to ward off ghosts of sunburn-averse Spanish settlers. Book at least a couple weeks ahead, especially if you want a room in one of those charmingly creaky inns that feel haunted-but in a cozy, grandmotherly way. Budget about $150-200 a day, leaving yourself plenty of wiggle room for impulse buys of pirate-themed memorabilia or artisanal soaps you definitely don't need. Sure, America's Oldest City is touristy, crowded, and just a bit kitschy, but that's precisely its charm-and besides, any place founded by stubborn Spaniards, attacked by pirates, swapped between empires like a hot potato, and still around to serve overpriced ice cream is absolutely worth your time, if only to say you've shared a beer with the ghosts of conquistadors past.