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On a charming corner of Greenwich Street in TriBeCa, the Greenwich Hotel is a sophisticated downtown Manhattan property co-owned by actor Robert DeNiro. Since opening in 2008, this boutique hotel has earned a reputation for its discretion (only a small sign signals the entrance), offering the type of service and privacy that attracts celebrity guests. Keep an eye out for abstract expressionist paintings by Robert DeNiro’s father, Robert DeNiro Sr., throughout the hotel.

No two of the 88 rooms are alike; the design is unfussy and pleasantly understated. Spacious bathrooms—finished in Moroccan tile or Italian Carrara marble—are a highlight of the accommodations. Start your stay with a swim in the lantern-lit swimming pool before sipping a pre-dinner cocktail in the guests-only drawing room, complete with a fireplace. The hotel is also home to neighborhood favorite Italian restaurant, Locanda Verde, from beloved NYC chef Andrew Carmellini.

This Upper East Side legend opened its doors in 1930 and, since then, has offered big-city accommodations to a legion of luminaries, from John F. Kennedy and Ingrid Bergman to the Duke and Duchess of Cambridge. The hotel’s famed restaurant Café Carlyle is where much of the action—and longstanding history—exists, having consistently hosted top talent like Woody Allen, Alan Cumming, and Rita Wilson since opening in 1955.

Pearl was founded in 1881 as a traditional brewery. These days, however, the bustling complex is less about beer than its 15 restaurants, dozen-plus retailers, and numerous family-friendly events, including a twice-weekly farmers’ market. Start with lunch at La Gloria, chef Johnny Hernandez’s nod to interior Mexico, followed by dessert at Bakery Lorraine, where you’ll find an enticing rainbow of Parisian-style macarons. If you’re in the mood to shop, pick up a tailored guayabera from Dos Carolinas, or a piece of handcrafted jewelry from Ten Thousand Villages. Pearl Brewery is even home to Hotel Emma, a true gem in San Antonio’s boutique-lodging scene, in case you don’t want to leave.

Find everything from candles and straw hats to t-shirts and fine resort wear at Basil’s Bazaar, a tiny boutique adjacent to the famous bar itself. Most of the goods are branded with “Basil’s Mustique” in one way or another, so everyone is sure to know where you’ve been—but that’s the point, right?

One of the five small, uninhabited Tobago Cays in the southern Grenadines, Baradel is home to brilliant white-sand beaches that double as nesting grounds for green sea turtles. On the southeastern shore of the island, there’s even a turtle reserve area, where you can swim alongside the graceful giants in a crystal-clear lagoon.

Near the wharf along upper Bay Street, a distinctive, street-level arcade connects several historic stone buildings, which once functioned as arrowroot warehouses. For centuries, these rows of Georgian stone arches and second-floor overhangs have sheltered Kingstown’s workers, walkers, and vendors from the hot sun and occasional shower—hence Kingstown’s nickname, the “City of Arches.”

A mile-long strip of soft white sand frames Friendship Bay on Bequia’s southern coast. The water here is consistently calm, making it perfect for swimming and snorkeling. You’ll likely have much of the beach to yourself—except for, perhaps, the area in front of the Bequia Beach Hotel, which welcomes non-guests to its lively beach bar.

You’ll likely do your sunbathing and swimming on the white-sand beaches of the Grenadines, but St. Vincent’s black-sand beaches are also quite stunning. In Biabou, for example, along the windward coast south of Georgetown, you can stare for hours at frothy ocean waves crashing onto the volcanic black sand. With luck, you’ll also catch a rainbow.

Explore underwater arches, tunnels, and grottos at this north island dive site—one of Dominica’s most popular descents. Here, blackbar soldierfish and glasseye sweepers patrol a sweep of exceptionally healthy hard and soft corals. Make sure to look down, where a fumarole releases bubbles on the ocean floor. Suitable for all levels, Toucari Caves has a max depth of 38 feet.

Part sustainable residential building, part eco-friendly lodge, the El Moore has been witness to Detroit’s turbulent history. The restored Victorian building boasts rooftop urban cabins, expansive suites, and bunk-bedded garden view rooms, covering various price points. Rooms feature reclaimed wood and subway tiles as well as ash paneling, geothermal heating, and solar paneling.

Located in the heart of the Cape Winelands, Terbodore Coffee Roasters imports beans from 13 countries, but also sources coffee from South Africa’s countryside. Stop in to try the roastery’s famous flavored coffees, or go for breakfast and pair a perfectly made flat white with sweet corn fritters and homemade granola.

Dominica’s most established contemporary artist, Earl Darius Etienne produces social realist paintings, often made with smoke and soot. One of his more famous works, the Massacre Mural, is a bright, in-your-face depiction of British troops slaughtering the indigenous Kalinago people. Check out his masterpieces at various island galleries, including his own Art Asylum in Mahaut.

For a refreshing swim, head to this deep mountain pool, which shines turquoise in the afternoon sun. On the upper reaches of the Hampstead River, the swimming hole even has a natural waterslide, fashioned from smooth, chafe-free rock. Pack and picnic and wear shoes suitable for the moderate rain forest hike in (1–2 hours roundtrip, depending on your route).

Husband and wife team Braden Perkins and Laura Adrian opened this restaurant in the “très Brooklyn” style that’s so popular in Paris now. The food is of American influence, but is made with fabulous French ingredients. We love going here.

An easy, 10-minute trail leads to these paired cascades on the west side of the mammoth Morne Trois Pitons National Park—the higher, lefthand fall is known as Father (279 feet) and the smaller as Mother (131 feet). While the path stops at the viewing platform, visitors often descend and bathe in the pools, moving cautiously over the slippery rocks.