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Go Bar occupies an old colonial house on a leafy Mendoza street (formerly Winery & Company). Its old, worn wooden floors speckled with sunlight have just the right vintage feel for wine browsing. It’s several rooms are stacked with wrought iron shelves featuring the region’s numerous wine labels. The staff is friendly and knowledgeable and will give you the perfect packaging to carry wines in your suitcase back home. Chile 898 (corner of Montevideo)

Mandarin Oriental’s first Caribbean resort has all the amenities you’d expect from the luxury brand—with the price tag to match. Nestled within lush greenery overlooking the white sands of Godahl Beach, the 26 suites and villas, which sit on the grounds of a 1,200-acre estate on the island of Canouan, are elegantly appointed with modern furnishings, marble baths, and rosy accents befitting the hotel’s name. Here, though, it’s all about the public spaces, including a Jim Fazio–designed golf course overlooking sparkling blue waters, a hilltop spa specializing in island-themed treatments, and four elegant restaurants serving every kind of cuisine, from pan-Asian to Italian. At Turtles, a cocktail lounge straight out of the Hamptons, opt for the Pepper Bliss, made with rum, bell pepper syrup, and pineapple juice.

Founded in 1558, Bayerische Staatsbibliothek is a historic, expansive, and important universal library. With almost nine million volumes and countless reading rooms, this is the perfect place to become lost in a text, work remotely, or explore with the family. Since 1663 they have collected copies of almost every Bavarian printed text—making it a wonderful place to learn about the regional culture and heritage. It’s also a lively cultural space that hosts regular exhibits and events. Come here either to marvel at the architecture, history, and texts or to get lost in a book. If you’re just passing by, be sure to check out the famous stone statues adorning the flight of stairs known as “the four magi.” See if you can guess which scholastic founders they represent!

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?

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.

The moment the snow melts, young Torontonians begin their annual spring migration to Trinity Bellwoods Park. The hippest park in town, Bellwoods stretches from the shopper’s paradise of Queen West up to central Dundas Street. On a summer’s day, sun-and-fun seekers spread out on beach blankets to watch the action: at the dog run, on the tennis courts, in the kiddie pool, and even closer, on the adjacent blankets. After dark, head to nearby Bellwoods Brewery for a pint.

The smallest holding in the mini-empire of Uri Jeremias, who also owns Akko’s Uri Buri restaurant and Efendi Hotel, this bright and no-frills ice cream shop sits along the old city’s western seafront. These are natural treats, made using local dairy products and no powders or stabilizers. The result is smooth and creamy, and the flavors (up to 16 available at a given time) are ones you won’t find too many other parts of the world, such as date, halva, cardamom, and rose.

A favorite among beach bums, yachters and rock stars, Basil’s Bar, on Mustique, is a legend in the world of beach bars. The second Basil’s brings some of the flavor of the original to Kingstown. Located near the Cobblestone Inn, the bar/restaurant serves a West Indian buffet at lunch as well as soups, salads, sandwiches and more substantial entrées.

When La Soufrière erupted in 1902, lava flowed down to the sea and created a five-mile-long moonscape on the volcano’s east slope. Today, if you visit during a tropical rain shower, you’ll see the riverbed transform almost immediately from a mere trickle to a gushing stream—and, because of its porous lava base, dry up just as quickly.

A Carib chief and national hero, Joseph Chatoyer led revolts against British colonists in 1772 and again in 1795. During the latter revolt, his soldiers and their French allies were planning to attack Kingstown from Dorsetshire Hill, but British soldiers marched up from the city and attacked first, killing Chatoyer. Today, he’s memorialized in a monument on that very hill, overlooking the city he fought so hard to regain.

Bookstore Bar & Café combines two of life’s great pleasures: books and booze. This hotel bar focuses on scotch and whiskey (over 130 varieties), though they also serve up carefully made craft cocktails; we liked the the Rum Daisy (light rum, lemon, house-made grenadine). At happy hour, you can nibble on small plates with charcuterie, cheese, or fried padron peppers, too. And if you see a book you like, they’re all for sale.

A tiny, man-made island in Clifton Harbour built with discarded conch shells, Happy Island is really just a small bar where you can tie up for a while and have a drink, a meal, and a conversation with Janti Ramage, the island’s joyful builder, owner, and operator. Just be sure to call ahead, as Ramage keeps flexible hours.

On the leeward side of Union Island, remote Chatham Bay Beach—one of a dozen on the island—is a favorite anchorage for boaters, a peaceful spot for sunbathers, and a great location for snorkelers. If you’re coming by land, there’s a trail that leads right down to the beach. There’s also a bar and a couple nearby restaurants should you get hungry from all that relaxing.

A 100-foot schooner based in Bequia, The Friendship Rose takes passengers on daylong cruises to Tobago Cays for snorkeling and swimming with sea turtles, or Mustique for beaching, bar hopping, and relaxing. Excursions include breakfast, lunch, afternoon tea, and drinks throughout the day, including beer, fruit punch, and soft drinks. Whether you opt for the marine park or the private island, the entire family is sure to enjoy the experience.