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Pretty Hotels founder Robert Kittel maps out the ultimate European road trip—winding through the Alps, Austria’s Bregenzerwald, the lakes of northern Italy, and down the Ligurian coast into Provence.

Drawn by years of whispered recommendations, Alexander Lobrano headed to the Costa Brava to stay at Hostal Empúries, a century-old seaside hotel built for archaeologists excavating the nearby Greco-Roman ruins, and gently modernized in the years since without losing its Catalan soul.

In the endless quest for the family beach getaway that’s easy yet tasteful, designer Naina Shah combined two very different stays on the Yucatán coast: one social and polished, the other slower and more elemental.

Almost like a village in Mayfair, Mount Street has become a destination in itself. Yolanda spent the weekend moving between some of the area’s best addresses, stopping for oysters at Scotts, custom slippers at Arthur Sleep, dinner at Jamavar, and martinis and an overnight at the Connaught, finding little reason to leave the neighborhood.

Designers Leanne Ford and Grace Mitchell have been coming to Round Top—home to the famed semi-annual Antiques Fair—for years, and share where to stay, the can’t-miss stalls, margarita spots to refuel, and how to get your haul home.

High on the bluffs above the Mississippi River, Natchez is a town rich with history and contradiction, where old Southern traditions meet a subtle creative revival. Photographer Ken Kochey, who splits his time between NYC and this soulful southern outpost, shares his favorite addresses, from biscuit breakfasts and a blues room to innovative art galleries…

For photographer Anna Pihan, a loosely plotted line on Google Maps became a 2,500-mile road trip that took her across New South Wales: through sandstone cliffs, ancient lake beds, old mining towns and sheep stations, capturing the magnetic pull of the Australian landscape.

About two hours south of Brisbane, Byron Bay is a place where the sun just seems to shine a bit brighter. While the main beach town has long been the draw, the wider Byron Shire and its hinterlands are what keep people coming back—or convince them to never leave.

Clara Hranek returns to western Scotland to explore a few places she never quite got to know. On Arran days are spent on misty coastal drives in a Unimog, exploring a baronial castle lined with stag heads, lunch with a 6th-generation farmer and her Highland cows, and even a stone-carved seaside bathing pool. Back in…