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One can’t help noticing Brazil’s stark social contrasts, especially visible in Rio thanks to rich neighborhoods that often sit cheek by jowl next to some of its poorest, the city’s famous favelas. High up in the favela called Tavares Bastos, visitors can take in an evening that includes some of the city’s best jazz, yet in a setting like few others: a boîte called The Maze. The owner, a British artist and longtime Rio resident, first decided to mount a First Fridays show in 2005, and those monthly events have become a citywide musical tradition. Those who journey up—aboard a minibus or in a taxi—will get breathtaking vistas to go with the great entertainment.

A long jetty with a thatch-roofed shelter at the far end is the signature motif of Pigeon Point Heritage Park. This is Tobago’s favorite swimming beach, a classic scene of golden sands bordered by coconut palms. The well-maintained 125-acre park is also a hub year round for island events, from dragon-boat races and culinary feasts to jazz and other music festivals. Colorful glass-bottomed boats pick up visitors here for tours over the ample reef system. And there’s shopping, too: Look for island-made ceramics, batik and beachwear.

With a name like that, it’s no wonder this boutique hotel is a prime spot for romantic getaways in the Yucatan’s capital city. The two pink-hued colonial mansions are as charming as they are camera-friendly, bedecked in vibrant modern art and picturesque patios and outdoor corners that mix lush greenery and sleek furnishings. Life here feels like its perpetually viewed through rose-colored glasses, and it’s not just the walls: the spa offers an enticing menu of xocolatherapies; the tequila bar has over 250 varieties to sample; the oasis-like swimming pool is a palm-shaded spot for afternoon dips; and there’s even a chocolate shop on-site. Guests can dine on gourmet fusion fare in the restaurant, or head up to the rooftop lounge for cocktails with a side of live jazz. As for the guest rooms, they’re no less indulgent with their rose and cocoa palettes and patterned-tile floors; minimalist bathrooms have sumptuous open-air stone tubs, large walk-in rainfall showers, and handmade chocolate soaps.

The São Pedro de Alcântara lookout may not be Lisbon’s highest viewpoint—that honor goes to the Nossa Senhora do Monte lookout—but it’s certainly its most romantic, offering panoramas of the city’s signature fortress, Castelo de São Jorge, perched ominously on the opposite hillside. In addition to the vista itself, the area offers pleasant gardens, which are perfect for lazing about, and a kiosk that regularly hosts jazz and other live entertainment. Come here at sunset and enjoy a sundowner as the city lights up below, then head to nearby neighborhoods Bairro Alto or Príncipe Real for a night on the town.

Fleetwood Mac front man Mick Fleetwood is behind this bar and restaurant, located on a third-floor rooftop in Lahaina. Here, guests sip drinks under beige umbrellas while taking in views of the dreamy blue Pacific. To pair with award-winning cocktails like the Heart of the Jungle (Cynar, Velvet Falernum, coconut rum, and lemon juice), which comes in a tiki artichoke, executive chef Eric Morrissette serves a menu of elevated bar bites, fresh local fish, and meatier dishes like filet mignon with peppercorn reduction. If you’re not a cocktail person, know that the robust drink menu also features beers from Maui Brewing Co. and Kohola Brewing as well as exclusive wines like Krug Brut from Reims, Luberri Gran Reserva rioja, and even a Chateau Musar red blend from Lebanon.

Place des Arts, the jewel of the Quartier des Spectacles in the center of town, is a cultural complex attached to the Musée d’art contemporain de Montréal that unites five performance spaces, including the Maison Symphonique de Montréal. It has two main performance arts spaces: Théâtre Maisonneuve, a nearly 1,500-seat modern-day rendition of a classical Italian theatre where dance organizations including Grands Ballets Canadiens regularly perform; Salle Wilfrid-Pelletier, which with just under 3,000 seats is better suited for big, boisterous Opéra de Montréal productions; and the smaller, 400-seat Cinquième Salle, home to series of shows by Danse Danse, among others. Photo: Susan Moss

Kids visiting the Westin will love the resort’s kiddie pool, featuring an enormous waterslide that will make adults envious. There’s also a large indoor-outdoor play area (packed with toys!), mini putting green, and sandbox.

The Louisiana-style, year-round barbecue at Buster’s is in a league of its own. Main-course options at this no-frills (read: It’s a glorified picnic shelter) Calistoga eatery include shoulder, pork ribs, tri-tip, chicken, pork loin, and pulled pork—all cooked medium rare unless otherwise specified. Most dishes come with sides such as baked beans, macaroni salad, and cole slaw. All portions are heaping, and every dish comes with signature garlic toast. Dessert options include house-made sweet potato pie and fresh-baked cookies. Because of Buster’s proximity to downtown Calistoga, the restaurant is a great stop after a morning hike on Mount St. Helena. On warm days, try to grab a table outside and watch the ‘cue masters work the outdoor grills, and on Sunday afternoons, stick around for live blues and jazz on the patio.

Chef Laurent Tourondel’s LT Steak & Seafood, located inside the historic Betsy Hotel on Ocean Drive, is popular not just with hotel guests but locals as well, who stop in for an afterwork cocktail or a nice night out. The restaurant does what its name indicates, and the menu is evenly divided between prime cuts of porterhouse and rib eye and fresh seafood from local waters and elsewhere, as well as sushi, sashimi, and ceviche. At dinner, there is often live entertainment such as jazz in the conservatory or a performance by an opera singer.

Jambe de Bois is an unpretentious food escape set idyllically in Pigeon Island National Park. The café—made of stone, driftwood, and thatch—serves up a beach view, an island atmosphere, and a simple menu that will keep you happy for hours. Sit on the deck at one of the picnic tables, and snack on sandwiches, salads, or local dishes like rotis, curries, or fish fillet with rice and peas at lunch and dinner. Come for happy hour or join the locals for live jazz on weekend evenings. The local art on display inside is for sale.

Prague’s centuries-old connection to music survived occupation by both the Germans and the Communists, so it’s fitting that those deep roots strike a chord at Aria Hotel Prague, where all of the rooms are named after famous composers or singers, from homegrown sons like Dvořák and Smetana to contemporary icons like the Beatles, Ella Fitzgerald, and Elvis Presley. The hotel even has a music director who can point you to the city’s best performances, as well as assist with suggestions in the music library; guests borrow CDs or concert DVDs to watch in their rooms, which are all outfitted with hi-fi sound systems that include Marantz speakers, plus flat-screen TVs, Blue-Ray players, iPads, and Apple TVs. All 51 accommodations were given a head-to-toe makeover in early 2018, resulting in sumptuous rooms decorated in shades of soft peach, dusty rose, and sandy taupe, and combining a pleasing mix of antiques and modern furniture. During summer, the superb CODA restaurant commands stunning rooftop views, while the Winter Garden Atrium is cozy perfection in colder months with its piano recitals accompanying afternoon tea or wine.

For those who aspire to travel as trendsetters in Jamaica, it helps to know that Port Antonio, way out on the eastern end of the island, is the destination to head for. And the address to shelter at is the Trident Hotel, whose 13 waterfront villas would not look out of place on South Beach. Nor would the crowd that hangs around its infinity pool or in its restaurant, Mike’s Supper Club, where local musicians and the occasional celeb sit down to knock out tunes on the 1917 Ferrari-red grand piano. The Trident Castle, a kind of fantasy annex, is a former private residence whose grand rooms, sea-view terraces, and dollhouse-size chapel make it ideal for destination weddings. A hard road to get there? Not for guests who avail themselves of the helicopter pad.

With just a few tables and a handful of barstools, this bar may be tiny, but it packs a lot of character into its diminutive space. Walls are decorated floor-to-ceiling with a mix of beer posters and racy street art; at the small wood bar, eight curving brass taps dispense top-notch Belgian-style draughts like La Chouffe and La Trappe. Around 50 specialty beers are also available by the bottle, many of them rare craft brews. During evenings, the bar even manages to squeeze in a DJ, who spins funky old-school jazz.

This funky boutique hotel on the edge of the Britomart shopping district goes way back in Auckland history. Built in 1841 as The Commercial Hotel, the DeBrett building survived two fires and two rebuilds plus a stint as a hostel before becoming the quirky place guests experience today. The Housebar has always been the center of hotel life, and today, the intimate wood-and-mint venue exudes its original art deco style and serves classic cocktails and local beers and wines alongside refined pub snacks.

In addition to restoring the bar and adding a glass-roofed atrium that houses the hotel restaurant, DeBretts Kitchen, the current owners affixed contemporary artwork and photography throughout and sheathed the entire building in candy-striped carpeting, custom designed from 100 percent New Zealand wool. Besides the carpet and small-batch minibar selections, no two rooms are the same. Each features unique furnishings from the 1930s on, and every bed has an original screenprinted throw. Two of Hotel DeBretts centerpieces, the chandelier and water sculpture in the restaurant, were crafted by Auckland artists from materials salvaged during the latest renovation. The result is a local experience from top to bottom that gives guests a real taste of New Zealand.

Just when it seemed like the Riviera Maya Riviera had become nothing but a sea of all-inclusive beach resorts, you stumble upon the quaint little Mexican village of Puerto Morelos. There are almost no huge developments, no shopping outlets, and no chain restaurants. The place is absolutely magical and is like traveling back in time. There is a small town square or plaza lined with palm trees, small cafes, and local boutiques. You can always find a good margarita to sip on at the super hip little bars scattered around the small town. If you find yourself on the Yucatan peninsula don’t miss this opportunity to travel back in time 50 yrs and experience the “old” Mexico.