Palm Beach

An Everglades airboat tour isn't your average sightseeing jaunt-it's more like strapping yourself onto a glorified fan and hurtling wildly across a grassy river. It's equal parts exhilarating, deafening, and oddly primal, the Floridian answer to the African safari (minus the tasteful khaki and binocular envy). Aim for an early-morning or late-afternoon tour: gators are less lethargic, mosquitoes haven't yet mobilized into full military formation, and the swampy stillness feels like stepping into a National Geographic spread narrated by a vaguely sarcastic uncle. Plan at least a week ahead during high season (December to April), and budget around $30-$50, plus a generous tip-consider it hazard pay for your captain. Feel free to bring sunglasses, bug spray, earplugs, and perhaps a healthy sense of irreverence toward nature's efficiency in evolution. Sure, the Everglades might have been called the River of Grass poetically by Marjory Stoneman Douglas, but after a dizzying airboat ride you'll probably just call it the place you saw a creature older than dinosaurs lounging like a disgruntled leather sofa. Worth it? Absolutely, if only so you can casually drop at future dinner parties, "Did I ever tell you about the time I went airboating among prehistoric reptiles?"

Picture this: Sunday afternoon in Wellington, Florida-the bougiest equestrian playground you never knew existed-and you're perched in what feels like the front porch of Gatsby's weekend cottage, champagne flute in hand, watching impossibly tanned Argentine polo gods thunder down the lush green field on horses probably worth more than your house. The International Polo Club Palm Beach is where old-school aristocracy meets new-money bravado, where the divots in the grass get stomped back into place at halftime while impeccably dressed spectators air-kiss and gossip. Book a few weeks in advance if you want a coveted brunch table, or just roll up casually at noon with general admission for around $20 and pretend it's not your first time watching grown adults galloping after a small white ball. Dress code leans toward "garden party chic," so bring your biggest sunglasses and pastel-colored blazer, plus sunscreen-Florida's relentless rays don't discriminate. Ultimately, polo at Wellington is absurdly extravagant, completely unnecessary, and irresistibly fun. Even if horse sports aren't your cup of imported tea, you'll leave with unforgettable stories, envy-inducing Instagram posts, and perhaps a newfound appreciation for the ridiculous lengths humans will go for sport and spectacle.

Taking a day trip to Key West-an isolated spit of land at the flamboyantly quirky tail-end of the continental U.S.-feels a bit like plunging headlong into a Hunter S. Thompson travelogue, minus most of the intoxicants (or with them, if that's your style; Hemingway would approve). Your drive along the iconic Overseas Highway slices through seas so turquoise they could make Instagram influencers weep, and deposits you squarely into a land of free-spirited oddballs, chickens strutting down Duval Street, and old sea captains who claim they've seen it all twice. Arrive early-preferably shortly after sunrise, when the morning sun bathes those pastel-painted cottages in a soft, forgiving glow (the better to Instagram, my dear). Budget at least $150-200 per person to properly indulge in fresh Cuban coffee, fresh seafood pulled straight from the waters beneath your feet, and a kitschy souvenir or two (because who doesn't need a neon pink flamingo magnet?). Bring sunscreen, sunglasses, and perhaps a good dash of patience or irreverence for navigating the inevitable crowds near the Southernmost Point buoy. Sure, Key West is touristy and occasionally surreal, but it's also wildly authentic-a colorful, sun-bleached circus of history, eccentricity, and absurdity. And trust me, even if you don't remember every detail afterwards-on account of the rum cocktails or heat-induced delirium-you'll at least come home with one hell of a story.