Cape Liberty

If you find yourself wandering Princeton's pristine Ivy-clad paths, crisped to perfection by three centuries of academic bravado, consider hopping onto a historical tour. Sure, you could just wander aimlessly, pretending alums Einstein or F. Scott Fitzgerald might casually emerge from gothic archways to debate relativity or Gatsby's moral compass-but why not let a guide regale you with scandalous trivia behind Princeton's austere facades? Aim for early morning or late afternoon to dodge throngs of wide-eyed parents and anxious teens nervously absorbing ambition like free Wi-Fi. Book at least a week ahead during peak university events, and bring comfortable shoes, a curious spirit, and about twenty bucks-enough for the tour, with spare change to caffeinate yourself afterward at Small World Coffee (where future geniuses caffeinate daily). You'll walk away richer in tales of ghostly encounters, Revolutionary War hijinks, and the bizarre rites exclusive to Ivy League lore. Even if the closest you've come to an Ivy education is binge-watching collegiate rom-coms, it's worth doing-for bragging rights alone-inserting casually at dinner parties, "Well, when I visited Princeton..."

The Newport Cliff Walk is precisely the sort of elegantly impractical pursuit you'd expect from a place where Gilded Age tycoons once tried to out-mansion one another along rocky shores. Stretching 3.5 miles wedged stubbornly between audaciously lavish estates and an explosively photogenic coastline, this is where conspicuous wealth meets Mother Nature at her most dramatically indifferent. Come early-preferably sunrise early-to dodge the selfie-stick wielders and watch the Atlantic batter the cliffs with the cheerful indifference of centuries. Pack decent footwear (flip-flops are asking for disaster), a water bottle, sunscreen, and a pocketful of patience for maneuvering around distracted mansion-oglers. Budget is refreshingly minimal: the walk itself won't cost you a dime, leaving your wallet free to tackle a well-earned lobster roll afterward. Plan ahead if you're visiting in high summer, when parking spots vanish quicker than free beer at a frat party. Sure, it's gloriously touristy, even borderline cliche, but strolling past overly ornate mansions once occupied by characters with names like Vanderbilt and Astor, all the while the salty sea air whispers dark secrets of parties long past-it's worth every step, even if just to say you've brushed up against history's extravagant absurdity.

Forget what you've heard about New Jersey being all diners and turnpikes-Cape May whale watching is the state's salty, splashy rebuttal. This charming Victorian-era beach town, perched on Jersey's southernmost tip, offers front-row seats to nature's most magnificent ballet, featuring humpbacks and dolphins pirouetting through waters once prowled by swashbuckling smugglers and bootleggers fleeing Prohibition agents (yes, your relaxing whale watch doubles as a quirky maritime history lesson). Book your voyage at least a week ahead, and opt for early morning or late afternoon sailings to skip the midday crowds and snag the best lighting for your envy-inducing Instagram snaps. Pack some sunscreen, shades, and your sense of equilibrium-expect to spend around $50 per person, possibly an extra twenty if you succumb to onboard snack-bar temptation. Even if the whales pull a diva act and stay elusive, you'll come away with salt-crusted hair, a newfound respect for New Jersey's coastal charisma, and at the very least, one hysterically embellished nautical tale to regale your skeptical friends back home.

Overnight camping in the Catskill Mountains is the outdoorsy equivalent of stumbling into an eccentric, moss-covered tavern where Washington Irving might have dozed off after one too many pints-primal yet charmingly genteel. Come twilight, as the day's swarm of Instagram influencers disperses back to Brooklyn, this rugged slice of upstate New York reclaims its hushed grandeur: starry skies draped dramatically above leafy canopies, waterfalls murmuring secrets better left unheard, and trails whispering tales of Rip Van Winkle's epic snooze. Plan to stake your claim to a campsite several weeks out-these grounds fill up faster than brunch reservations in Williamsburg-budget roughly $30 to $40 for campsite fees, pack layers (the Catskills are reliable as your erratic ex on temperature swings), and stock adequate snacks, ideally something local and indulgent like artisanal beef jerky or regionally brewed craft beer. And for heaven's sake, remember the bug spray-Catskill mosquitoes are famously relentless, perhaps still embittered by the Dutch settlers who disrupted their idyllic forest back in the 17th century. Yet despite (or perhaps because of) the mosquitoes, the rugged trails, the finicky weather, you'll return home with just enough dirt under your nails, whiskey in your flask, and absurd stories of midnight rustlings in the bushes to make you the hero of your next dinner party.