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On first glance, it would be easy to dismiss the 101 Hotel as merely a functional option. Stepping inside the austere five-story concrete building on Hverfisgata, however, guests discover an ultra-modern boutique lodging with minimal black-and-white decor—the work of owner-designer Ingibjörg S. Pálmadóttir—that gives it the feel of a chic downtown gallery. Contemporary paintings, photography, and sculptures by local artists appear througout the property, complementing the oak floors and wood-heavy Nordic furniture in the 38 rooms. Queen and king-size beds (there are no twin rooms) come topped with fine Italian linens, entertainment systems are state of the art, and open-plan bathrooms make extensive use of glass and offer Aveda bath products; deluxe rooms and suites up the ante with with claw-foot tubs. The hotel also has a moody restaurant and bar, a gym and spa, and a comfortable lounge area where you can put your feet up by the fire.

No shopping trip in Windhoek is complete without a stop at the Craft Cafe. A small brewery and warehouse space has been converted into a venue for shopping and dining, featuring many local artisan products from around the country. On the top floor, the restaurant Craft Cafe serves an excellent Western-style breakfasts and large mugs of coffee at a reasonable price. Sit on the balcony overlooking the complex for a dose of fresh air while you dine. A small, secure parking lot is available to park if you have your vehicle with you.

Foodies (and those simply interested in local color and a good meal) should head to San Lorenzo and its covered Mercato Centrale. Florence’s main market for edibles is housed in a 19th-century glass-and-iron building. On the ground floor, delis, stands, and butcher counters sell a fantastic array of local fruit and vegetables, cheeses, dried porcini mushrooms, baked goods, balsamic vinegars, and olive oils plus fresh fish, poultry, and meat. Upstairs, a modern food hall has opened: Stalls sell prepared foods and meals for happy and immediate consumption at a central seating area.

On the non-descript, busy corner of Bucareli and Morelos streets in Mexico City is a café with a famous history: Fidel Castro and Che Guevarra met here at Café La Habana several times, chain smoking and drinking strong coffee, to plan the Cuban Revolution. Nowadays, you can still get excellent coffee—and pretty good food—while you plan something a little less dramatic (but more enjoyable), like your vacation itinerary. Old journalists and businessmen congregate here for hours on end while salt-of-the-earth, slightly surly waitresses take your order and bring you your food and drink. Come for breakfast and order their chilaquiles, motuleños, or molletes, and wash it down with an espresso or café americano.

Of all the accommodations in Maui’s tony Wailea resort community, the 22-acre, waterfront Fairmont Kea Lani may be the most family-friendly of the bunch thanks in large part to its all-suite-and-villa setup. The property’s 450 guest rooms are some of the biggest on the island—the smallest suites start at a generous 860 square feet, while the two- and three-bedroom beachfront villas weigh in at 1,800 square feet and up. All cater to families, with separate sleeping and living areas, entertainment systems, furnished outdoor space (for lounging and dining), sleeper sofas, and some type of kitchen facilities, while villas encourage group gatherings with plunge pools and BBQ grills. Both adults and kids will love the deep-soaking tubs, too. Elsewhere, three indoor and three outdoor pools provide space for fun when kids’ club activities (among them volcano building, hula lessons, and tide pool excursions) aren’t on the agenda. Grown-ups can also amuse themselves with activities like outrigger canoe journeys, cultural programs, tee times at three nearby championship golf courses, and locally inspired treatments at the Willow Stream Spa, which offers dedicated fitness and wellness programs. Fuel your adventures at the five on-site restaurants, including the seafood-focused Nick’s Fishmarket Maui (with its 2,000-bottle-strong wine cellar) and the award-winning Kō, where the flavors are inspired by Hawaii, the Philippines, Korea, and beyond.

For a taste of Miami by way of St. Lucia, look no further than Sugar Beach. Set on a white-sand crescent between the Piton mountains—within a 100-acre former sugar plantation studded with shady palm trees—the resort’s white-on-white cottages have all the amenities worthy of a five-star retreat, from sumptuous Egyptian cotton linens to butler service and access to a private chef. (No wonder Gwyneth Paltrow and Matt Damon have stayed here.) But don’t linger too long in your room. The coral reefs in the bay are home to triggerfish, turtles, and exotic sponges that can be viewed on an instructor-led dive or snorkel trip, and whale-watching, waterfall hikes through the rain forest, and adventure tours on ATVs await. If you have more leisurely pursuits in mind, the tree-house spa offers treatments using locally sourced ingredients for the ultimate in relaxation.

Esperanza, an Auberge Resort, sits on the southern tip of the Baja California Peninsula, offering guests exceptional views of the Sea of Cortéz. Each of the hotel’s 57 rooms faces the sea and Esperanza’s private beach but also offers access to four separate swimming pools. Hotel staff keep guests as busy as they want to be with a full schedule of activities, some of which are the usual Baja resort suspects like yoga lessons and cooking classes. A number of options are quite unique, however—book a master tequilero to teach you about the fine art of tequila appreciation, or take classes in Spanish, salsa, painting, and more. Guest rooms are gorgeous, with an earth-tone color scheme and fine, locally made handicrafts as decorative accents. Bathrooms in the casitas look out onto water, while villas have full kitchens and dining rooms.

A trendy restaurant that draws both local and international diners, i Latina offers funky décor, inventive cocktails, and eclectic cuisine with Mexican, Asian, and Mediterranean flavors. Opened in 1999, the restaurant was a pioneer of contemporary cuisine in Guadalajara. Snag a table on the terrace for a great view of the city.

You don’t have to go far to find fun at Hawks Cay, nor do you have to go far to relax by the water there. The resort, which takes up much of tiny Duck Key, is known for its lagoon, five pools (including one reserved for adults and another featuring a pirate ship slide), and a Dolphin Connection program that offers complimentary viewings and hands-on experiences. Water sports are plentiful as well, with kayaks, paddleboards, and boats to rent, and guests can book fishing trips, scuba and SNUBA diving, and kiteboarding instruction. There’s also a Cliff Drysdale tennis program, a spa and fitness center, and a kids club. The resort closed for one year after Hurricane Irma, reopening in September 2018 after a $50 million renovation to the main hotel, a project that included the redesign of all 177 rooms and suites, as well as the creation of a new upscale steakhouse, a seafood-focused café, and a marketplace with to-go options—these supplement the three poolside grills and cocktail bars. Privately owned two-and three-bedroom homes are also available to rent through the resort.

Since its founding in 1903, the DMA (as locals call it) has grown to become one of the top 10 largest museums in the country, with a permanent collection of over 24,000 works culled from around the globe and spanning over 5,000 years of history. Works by boldface Western names like Renoir, van Gogh, Warhol, Rothko, O’Keeffe, and Wyeth lead to extensive collections dedicated to art and antiquities from Africa, Asia, and South America; in between, limited-run exhibits might focus on Native American works, Asian textiles, or emerging contemporary artists. In addition to hosting popular events that engage the whole family, the museum is also committed to supporting Texas artists via foundations and special programs, and offers a searchable Texas artists database to help spotlight these native sons and daughters. Dine on casual, gluten-free Mediterranean fare at the plaza-side Socca, or head to the ever-popular DMA Cafe—set in a striking atrium—for globally flavored dishes inspired by works in the permanent collection.

This perennially popular bakery and sandwich spot can feel somewhat out of place. With its cozy atmosphere in a plant-filled space, and its menu of warm panini, delicious sandwiches on artisanal breads, generous salads, and perfectly executed pastries, it is the sort of restaurant you’d expect to find in one of Montréal’s cooler neighborhoods. Instead, it’s in the heart of Old Montréal. That is a definite plus for travelers visiting the city’s historic sights. It also means, however, that there is a lunch-hour rush when nearby office workers vie for tables. If you can plan on an early or late lunch—you’re on vacation, after all—you can avoid the worst of the crowd. Olive et Gourmando is open from 9 a.m. to 5 p.m., so if you are looking for a place for dinner, the same owners are behind the new Foxy (in the Griffintown neighborhood), which is quickly proving as popular as their first restaurant.

Is Bar Agricole the best bar in the city? It’s certainly in the top five, based on the groundbreaking cocktail program developed by bartender and owner Thad Vogler; the award-winning architecture and interior design by local favorite Aidlin Darling; and a daring menu centered around produce from nearby organic and biodynamic farms. Vogler used to bartend in Tokyo, and his obsession with Japanese precision shows. You’ll see influences of that in the hand-cut ice cubes he uses, and in Agricole’s glassware and aprons (all from Japan). The bar stocks a limited selection of 20 or 30 spirits, almost all small batch, and with a special focus on rum. Come for drinks, come for dinner, or come for brunch: the midday menu highlights include ricotta doughnuts with quince marmalade and a chicory salad with fuyu persimmon and house-made vinegar. Pro tips: In winter, book the private dining room (nicknamed the Grotto) for a seated, though still laid-back, dinner for up to 32 people; for an outdoor event, Bar Agricole’s covered and heated patio is perfect for larger, more casual groups. For lessons in liquor, check out the private spirits tastings that Vogler offers through IfOnly.

Located on a half-mile stretch of white-sand Ha My Beach, a short drive from the UNESCO World Heritage town of Hoi An (a hotel shuttle can ferry you back and forth), the Nam Hai sits on the grounds of a former fishing village (a temple from that time is preserved on-site), and it still feels like a community. Guests bike between public spaces designed to evoke the high-ceilinged Tu Doc royal tombs found in the region, as well as 86 acres of tropical gardens and 100 villas, each outfitted with indoor/outdoor lounging spaces, king beds, lacquered bathtubs, and alfresco showers. The dining options range from a casual beachside spot to a fine-dining restaurant, and serve everything from Vietnamese and Western fare to Indian tandoori specialties; learn how to make some of your favorite dishes in a chef-led cooking class, or join the kiddos at the Junior Cooking Academy, part of the kids’ club. When you’re ready to take a break, don’t miss the central trilevel infinity pool and the exceptional spa, where the eight individual treatment pavilions appear to float on a koi-filled lagoon.

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.

Playa del Carmen’s winning charm emerges all along this wide pedestrian avenue, which runs parallel to the beach. Eateries here include everything from cheap fast food like Pizza Renzo to upscale restaurants and cafes; the best people-watching is from outdoor seating at the sports bar Tequila Barrel or Chez Céline bakery. The shopping scene offers international luxury brands side by side souvenir shops, but the most interesting Mexican handicrafts await at boutiques like Sin Pecado and Sol Jaguar. Since this part of town has little shade, it’s best to avoid the midday sun; instead, try an early-morning visit with some streetside coffee in hand, then revisit at sunset to kick off an evening of dining, shopping, and bar-hopping.