On a pristine peninsula on the quieter side of St. Barth, Rosewood Le Guanahani is a polished French-colonial resort on a sparkling turquoise lagoon. Come for airy private cottages, mornings at Rosewood’s signature Sense spa, and access to the breeziest version of yourself. The warm, doting staff somehow intuits and offers whatever you need—a piña colada, a beach towel, a bookmark—the moment before you realize you need it. You can fill your days with sunrise hikes, windsurfing, and snorkeling if you’d like. But you could also simply while away the hours bouncing between the sand, your sundeck, and the excellent on-site restaurant, Beach House.

You’re within a 20-minute drive of just about everything the island has to offer. Visit Grand Fond after the tide goes out to swim in crystalline natural pools. Saline Beach is as remote and unspoiled as it gets. (It’s also clothing-optional, so if you are inclined toward skinny-dipping, this is the spot.) Al Mare, at the neighboring hotel Le Sereno, serves up seriously legit Italian and one of the coolest social scenes on the island. For late-night dancing, there’s Le Ti. And don’t skip Gustavia, the island’s capital: Stroll the cobblestone streets, do some window- (or actual) shopping, get cocktails at Bonito, and ogle the superyachts in the harbor.

In New Orleans’s Lower Garden District, Hotel Saint Vincent is a gorgeous compound—75 rooms and three restaurants surrounding a courtyard pool and bar—toward the east end of Magazine Street, just a short ride from the French Quarter. It has a relaxed, partyish vibe that’s in sync with the spirit of the city, and the design is considered, down to the smallest details—like the pretty pink tiling in the bathrooms and the swish silk robes that match the marbled-paper walls. The cult-favorite Austin boutique ByGeorge has an outpost just off the lobby, which is either convenient or dangerous, depending on your perspective.

There’s no shortage of food and drink options within walking distance: French Truck, a popular local coffee roastery; Molly’s Rise and Shine, which serves collard greens, carrot yogurt, and fried chicken and biscuits for breakfast; and The Bower for farm-to-table new American and date-night vibes. On the far side of Magazine, La Petite Grocery, helmed by James Beard Award–winning chef Justin Devillier, dishes up contemporary Creole: Get the shrimp and grits, crab beignets, and just about anything off the inventive cocktail menu. If you want to venture farther afield, drop into one of the moody jazz bars on Frenchmen Street or head to Bacchanal, a wine-shop-turned-speakeasy that hosts killer backyard parties featuring local musicians.

A jewel-toned marvel of a boutique hotel, the Fife Arms sits right in the middle of the Cairngorms, the UK’s largest national park. Which makes it an ideal base for exploring the surrounding countryside, whether that means hiking in the hills, picnicking in the woods, or fishing in a local loch. But the real draw here is the hotel’s eccentric, expertly curated art collection. The property, owned by the gallerists Iwan and Manuela Wirth, is home to 14,000 collected and commissioned pieces ranging from 19th-century Victoriana to ultracontemporary works. Some highlights: The explosively colorful (and trippy) drawing room ceiling by Zhang Enli. A bleach-splattered Steinway by Mark Bradford. A Picasso. And a delicate watercolor painted by Queen Victoria herself.

On the property, you can take afternoon tea in the drawing room, choose from a library of whiskies at Bertie’s Bar, sip craft cocktails and champagne at Elsa’s (where the design pays homage to Elsa Schiaparelli and her signature shocking pink), and grab local beers and Scottish bar food at the Flying Stag, a proper pub and the social center of the town. The fine-dining restaurant, the Clunie Dining Room, focuses on wood-fire cooking and traditional Scottish ingredients.