Colonia del Sacramento

If you've ever fantasized about sipping wine amidst old-world charm without the pretentious fuss of Bordeaux or Tuscany, make your slightly irreverent pilgrimage to Los Cerros de San Juan-the oldest winery in Uruguay, nestled charmingly between rolling hills and faded colonial grandeur. Founded in 1854 (back when Napoleon III was making questionable decisions in France), this atmospheric wine estate invites you to swirl hearty Tannats and crisp Albarinos, nibble suspiciously addictive regional cheese, and learn why Uruguay might secretly be the coolest kid on the South American viticulture block. Go in the late afternoon, when the sunlight drenches the vineyards in a sumptuous golden glow ideal for envy-inducing selfies. Book at least a week ahead-locals love their wine as much as football-and budget around $30 to $50 for a generous tasting paired with cheeses that frankly deserve their own cult following. Bring a hat, sunglasses, and a sober friend willing to chauffeur your merrily intoxicated self home. Do it not only for the exquisite wines and languorous countryside, but because nothing spices up dinner-party banter like casually mentioning the afternoon you debated tannins and terroir while tipsily stumbling around Uruguay's oldest cellars.

Stargazing at Parque Anchorena isn't just gazing upward-it's communing with celestial poetry, Uruguayan style. Toss aside your flimsy city expectations of a night sky; here, amidst whispering eucalyptus trees and snoozing deer, the heavens unroll a glittering spectacle worthy of an out-of-body experience. Parque Anchorena itself bursts with quirky history: originally the extravagant estate of 19th-century Argentine aristocrat Aaron de Anchorena-who, let's admit, had superb taste in location-it's now Uruguay's best-kept nocturnal secret. To maximize cosmic awe, plan your celestial getaway during a new moon, arriving by dusk to claim your grassy throne (bring blankets, insect spray, and maybe a flask of something warming-you're welcome). Book at least a week ahead, spending around 20-30 dollars for a guided session that invites astronomically inclined locals as charming as they are knowledgeable. Even if constellations elude you and your only astronomical knowledge comes from Star Wars, there's a quiet giddiness in recognizing the Southern Cross or peering through a telescope for your very first glimpse at Saturn's rings. And if nothing else, returning home able to say you've star-surfed in a Uruguayan aristocrat's backyard has story-value enough to impress-or at least mildly bewilder-your friends.