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Two hours from Rio de Janeiro, off the coast of Angra Dos Reis, Ilha Grande makes for a spacious retreat for two or an epic group vacation. The private island’s six-bedroom house comes with kayaks and stand-up paddleboards, plus a staff ready to whip up caipirinhas at all hours of the day.

Located just two miles north of Port Elizabeth, on an 18th-century sugar plantation and working sea salt farm that overlooks Spring Bay, Firefly Bequia has all the sophistication of its sister accommodations on tony Mustique. Scattered along the hillside to maximize ocean views, the four suites and one two-bedroom cottage are outfitted with king-size four-poster beds, indoor-outdoor showers, and rattan ceiling fans that recall the island’s colonial past. Though it’s a five-minute walk to the beach, you’ll spot the remnants of the plantation’s original sugar mill, a croquet lawn and swimming pool, and the hotel’s resident goats along the way. Upon your return, a cocktail in the stone bar, where green bananas hang like chandeliers, is just the thing to ease you into a star-filled night.

Tempt fate at the Monkey Paw’s Book-O-Matic machine, where for the price of a toonie you’ll be delivered an archaic tome in the vein of Elementary Arabic, Vol. 3. I’ll let you know how my studying gets on. The Monkey’s Paw is an eclectic vintage bookstore on Dundas with a collection of unique books, vintage maps, and bugs preserved in Lucite.

If you’re looking for a party atmosphere and excellent people-watching, this restaurant/bar positioned near Hamilton’s harbor is your spot. It serves breakfast, lunch, dinner and late-night snacks. DJs spin and live music is performed throughout the week.

For more than two decades, Chef Volker Romeike’s standout restaurant has charmed patrons at the Sheraton Grand Los Cabos Hacienda del Mar with its Pacific Rim concept, ocean views, and dramatic design. Pitahayas—both space and the menu—got an updated look in 2015. A newer focus on blending Mexican and Asian flavors has allowed Romeike to show off his culinary creativity. Duck lumpia (like a spring roll) is served with a papaya salsa; a taro tostada comes topped with carnitas (braised pork); and tuna poke comes with watermelon and chili powder. For special occasions, consider the Cava de Santiago wine cellar, which houses some 400 vintages. The restaurant’s bar also offers Social Fridays, when limitless drinks can be had for a not unreasonable tariff.

While much attention is paid to the Japanese and Italian influences on Los Cabos cuisine, one of the very best spots in town is an Argentine entry. The low-key, low-lit courtyard restaurant Chamuyo features a dozen or so tables, a long bar, and a traditional Argentine grill. The steak-house menu sends you on a culinary adventure through Buenos Aires dance halls and the verdant pampas. Meat-stuffed Argentine empanadas (markedly different from the Mexican variety) are served oven-baked or fried, and make excellent starters. For your main course, try chef Marcelo Romby’s 22-ounce beef ribs, which he slow-cooks for more than four hours. Pair it with a bottle of Baja red and, if you can, save room for some first-rate alfajor cookies.

West Loop denizens can get their fill of locally made spirits at this distillery and cocktail bar, where cofounder and head distiller Tremaine Atkinson bottles up just about everything of an ABV nature—with a bespoke spin. Its vodka may be its flagship offering, but it’s proved its aptitude with a handful of other liquors as well, from gin and rum to amaro and limoncello. If you can’t make one of its Tuesday or Saturday tours, swing by anyway for a dram; a full cocktail list pairs up with bites throughout the week and features go-tos like the Cease & Desist, a melding of CH London Dry Gin, Lapsang souchong, ginger, honey, and lemon.

Servers, somms, and chef-owner Nancy Silverton all swirl around Osteria Mozza’s centerpiece Mozzarella Bar, where small dishes of freshly imported mozzarella, ricotta, and burrata are plated with pairings like bacon or braised leeks. With eyes closed, white-tablecloth diners attempt to fully savor each bite of cool, moist cheese before it melts in their mouths. These flavors are a tough act to follow, but the restaurant certainly steps up to the plate with signature meals like the Squid Ink Chittara Freddi with crab, sea urchin, and jalapeño. Just be sure to leave room for a rosemary olive oil cake for dessert: The eatery’s Dahlia Narvaez was awarded the James Beard Foundation Award for Outstanding Pastry Chef in 2016. Reservations at least one month out are recommended unless you have the flexibility to take a chance with a walk-in seat at the Mozzarella Bar itself—a one-of-a-kind experience.

This surf-style restaurant elevates local food-truck fare at the new Four Seasons Resort Oahu at Ko Olina. Expect ahi poke, wild-boar hot dogs, and the coolest French fry innovation out there: A heaping platter of slender spuds topped with Parmesan, cherry tomatoes, and wilted arugula for that “It’s healthy, really” feeling! Wash it all down with kombucha on draft—with flavors like pineapple ginger or liliko’i (passion fruit)—and cocktails such as the Castaway, featuring melon vodka, coconut water, and lime juice. Come prepared to lounge outside, as the Waterman wraps around the family pool and also serves its exclusive beach. Food is served 11 a.m. to 6 p.m.

A half-hour’s drive from Bridgetown on the east coast, these gardens on just 2.4 hectares (six acres) of lush grounds are home to an astounding variety of tropical and subtropical plants, from orchids to palms and species found only in Barbados. The gardens were the personal project of Iris Bannochie, one of the island’s leading 20th-century botanists, who began designing them in 1954 and left them to the Barbados National Trust upon her death in 1988. An on-site café is a good option for a light lunch.

Anguilla’s most social beach is full of local flavor. From visiting boats to residents who flock here for the best island-style bar-and-nightlife atmosphere—home to Johnno’s, Elvis’ Beach Bar, and the Pumphouse—there’s never a dull moment on Sandy Ground’s long, soft strand. The water here is calm, making it an ideal stretch of sand for families as well. Sandy Ground is also the site of Anguilla’s August Monday, the most important day of the summer carnival season, when the entire country seems to be in the same location to celebrate J’ouvert: some folks on the beach, some on boats blasting music. By 1 p.m., the August Monday sailboat race kicks off—the first round of qualifying for the final carnival boat race at week’s end.

The isolated, car-free island of Käringön is a 40-minute ferry ride from Orust, and has less than 100 full-time residents who stay year round, even through the long winter. But it’s a different story in the summer. In the 19th century, the middle classes in Sweden became enamored with the benefits of fresh sea air and started flocking to the small islands along the coast. Today about a thousand visitors arrive daily by ferry or private boat to enjoy the island’s relaxed vibe. Come for a lunch of fresh-caught seafood at Petersons Krog or watch children on the pier trying to catch the little crabs crawling through the seaweed down below. In the cold weather, visitors can take a lobster fishing tour or sample fresh oysters at the Käringö oyster bar, which also has a hot tub that seats six.

It is all about farm-to-table cuisine at Primo, where two-time James Beard Award–winning chef Melissa Kelly hangs both her toque and her garden shears. Behind the restaurant, in a Victorian house on the Rockland–Owls Head town line, are acres of pastures and organic gardens. Be sure to allow time to visit with the chicken and pigs, buzz by the beehives, ogle the greenhouses, and admire the produce, edible-flower, and tea gardens. Make reservations for the intimate and elegant Parlor dining rooms, or head to the upstairs Counter Room and Bar, where the menu highlights pizza, cheeses, and charcuterie, and tapas-size portions. The flavors are Mediterranean with a Maine accent. Don’t miss the house-made breads or desserts, either.

A short drive north of the South Island town of Oamaru, Riverstone Kitchen is often lauded as one of New Zealand’s best regional restaurants. The stylish dining room is anchored by a robust fireplace crafted from local river stones, and much of the seasonal menu is crafted from the restaurant’s own organic orchards and gardens. A more relaxed café ambience for daily breakfast and lunches segues to a more formal mood at dinner from Thursdays to Saturdays, and the savvy drink list includes wines from the nearby Waitaki Valley as well as small-batch beers from around New Zealand. Ask if any of the excellent Belgian-style farmhouse ales from Oamaru’s Craftwork Brewery are available.

There’s no shortage of great eateries in the New Zealand capital—reputedly Wellington has more cafés and restaurants per person than New York City—and Field & Green is a popular option for the city’s discerning diners. With a versatile menu bylined European Soul Food, it promises ever-changing weekly dishes that could include house-made pasta with wild mushrooms and blue cheese, or baked eggs with spicy lentils and mint yogurt. These hearty but sophisticated flavors are the ideal sustenance for daytime explorations of the city’s harbor attractions, and the good-value, Wednesdays-to-Saturdays three-course supper menu can be partnered with local Wellington craft beers or New Zealand wines.