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Two hours from Montreal, this secluded, family-run hotel is an elegant way to get a summer lake-life fix, with Québecois flavor.

In its 1960s jet-set heyday, Porto Ercole was more popular than Portofino. Today it’s more low key, and while it’s best known for being Il Pellicano-adjacent, it offers those not booked into its iconic hotel a restaurant-lined marina, pebbly beaches and family vineyards, with countless Tuscan villages a day trip away.

The westernmost inhabited Dalmatian Island, this former military stronghold was closed to tourism until the late ‘90s and remains blissfully off-radar—with limited ferry service, few hotels and no disco in sight.

Designer Amalie Moosgaard, cofounder and creative director of Copenhagen-based LIÉ Studio, road trips around this southern coastal region known for its surfing beaches, vintage markets and cozy coffee-houses.

Peter Som’s favorite salt-kissed cabins on a fishing wharf, go-to for a lobster roll, galleries that channel the town’s artistic spirit and the best spot to drop anchor & swim alongside pods of seals

Designer Nikki Kule on the quieter side of the largest Balearic island—the rustic family-owned restaurants, boat-access-only swimming coves, and the ceramics studio that is worth the trip alone

Habitually Chic founder Heather Clawson shares her annual trip to the most low-key village in the Hamptons

Bald eagles and whale-spotting, blood-orange sunsets and salmon on the grill, plus cold plunges into piney mountain lakes makes this largest of the San Juan islands worth the distance

A few days spent exploring the herb-scented, sun-splashed wild coast of Maremma, with its medieval villages, small family-owned wineries and one surreal sculpture garden