Anguilla 

The staff at the Viceroy Anguilla (viceroyhotelsandresorts.com) are on hand to arrange exciting excursions (a private scuba outing, a trip to a deserted island), but once you’ve settled into this ultra-chic hotel, you might not want to venture beyond the infinity pool. Designer Kelly Wearstler’s signature elegance is evident throughout the hotel, from the chic neutral palette to the driftwood sculptures. Don’t miss The Cool Stone Massage, which uses smooth, iced stones to revitalize feet and legs. The spa is housed in a villa overlooking the Caribbean, but you can always move your treatment to the beach.

Toronto

The latest outpost of the Thompson Hotel brand (thompsonhotels.com) feels like a love letter to the city. In the lobby, admire Spanish artist Javier Mariscal’s mural of the city skyline, then head up to the Rooftop Lounge to enjoy the 360-degree view for real. Don’t miss Milkshakes and mac and cheese at The Counter, the 24-hour diner that contrasts its comfort-food staples with art deco wallpaper and blue-velvet banquettes.

Milan 

Housed in a railway station that dates back to 1840, the Maison Moschino (maisonmoschino.com) combines super-sleek design with modern fantasy—each of the 16 room designs was inspired by a fairy tale. The Sweet Room—a nod to Hansel and Gretel—features pillows that are made to look like oversized cupcakes and a chandelier crafted from ceramic candies. Don’t miss The irony-infused menu at Clandestino Milano, which has sample offerings like mint-flavoured sake served with a toothbrush daubed with mint/coconut “toothpaste.”

Turkey

Five kilometres of subterranean tunnels connect the rooms at Argos in Cappadocia (argosincappadocia.com), a boutique cave hotel underneath an ancient monastery. The suites are the epitome of cozy luxe, with firelight flickering against the stone arches. Above ground, the area is dotted with peaks formed by volcanic ash and lava. Don’t miss A midnight dip in your own private underground plunge pool.

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