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Montevideo’s Ciudad Vieja, or Old Town, is located on a peninsula separating the Río de la Plata from the harbor. It has the orderly grid typical of many Spanish cities in the New World. Until 1829, the Ciudad Vieja was walled though today only one gate (the Puerta de la Ciudadela) remains of those defenses. This section of Montevideo is home to many of the city’s most famous historic buildings, including the cathedral and the Cabildo, which today houses the city’s archives.

Considered by some as a Milan institution, Cantine Isole is a small wine bar/enoteca with a lot of history and great atmosphere. It’s located in the Chinatown neighborhood, near Garibaldi station and the Isola neighborhood. Expect a lot of character.

Start your day at Deus Ex Machina, a motorcycle store in an alley full of them, whose café is the perfect spot for a cappuccino and soft scrambled eggs while you ogle the Ducatis.

T. Loafer is hard to miss thanks to its colorful exterior, patched together from more than 20 salvaged window frames. Order a cup of hibiscus lemongrass tea and a pastry made with locally grown fruit. The shelves are stocked with books, regional crafts, and photographs processed in the darkroom downstairs. 886/(0) 9-3781-7612. This appeared in the November/December 2012 issue.

This little market is full of treasures (and a few tourist souvenirs). What you get to experience here is everyone’s trade and how these crafts help support their family and village. Lots of things to buy...and they’re willing to bargain.

Just southwest of Astoria, Fort Clatsop replicates the encampment built by Lewis and Clark’s Corps of Discovery soon after they reached the Pacific. From December 1805 to March 1806, they hunted and gathered food, distilled salt, traded with the local tribes and documented their surroundings. The center includes the log fort (staffed by costumed rangers), an exhibit hall, a gift shop and films, plus trailheads for the Fort to Sea Trail and the Netul River Trail.

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.

Usually, when you travel, it’s to experience a different side of yourself. The more adventurous side, the slightly less scheduled side, the sleep-in-without-guilt side. And when you stay at the Drake Hotel in Toronto, you can’t help but feel like your cooler side is making a much-needed appearance. The recently renovated property on Queen Street West features the kind of interior design that radiates style whether it’s in the kaleidoscopic lobby, the next door theater, or in two wings of suites. That’s because the hotel commissioned artists to showcase their work on plenty of open surfaces — from a black-and-white squiggle accent wall in guest rooms to personality-driven drawings in the elevator — and the results make for surroundings that are the material equivalent of black sunglasses. Paired with of-the-moment details like pink terrazzo showers and wraparound midcentury sofas, and the Drake Hotel is meant to cultivate a see-and-be-seen vibe.

But that’s not to say that the hotel sacrifices comfort for being camera-ready. The staff is kind and always available through text, the beds are soft and squarely stationed in front of a well-appointed bar and flatscreen television, and designer toiletries are filled to the brim. It’s also possible to eat throughout the day at the hotel’s delicious cafe and patio (get the French toast), and then spend the night at its second-floor bar or ground floor lounge. On weekends, even if you’re not a guest, you can stop by for regularly scheduled events including a DJ who spins old and new tunes. If you do plan on leaving the hotel to see the city, then you’re right in the midst of it, and the surrounding neighborhood can keep you readily entertained.

When you stay at the Drake Hotel, don’t be surprised if you feel relaxed, in-the-know, and decidedly cooler once you check out. These are sides of yourself the hotel may have encouraged, but feel free to hold on to them after you return home.

Only in Rio can you happen onto a tropical paradise without leaving city limits. About 22 miles west of Copacabana lies Prainha. The name calls up a small beach that’s in fact a sand formation in an ecological reserve surrounded by the Atlantic Forest (Mata Atlântica), with its complete variety of plant and animal life. Known as one of the city’s surfing meccas, it’s a gem for anyone keen on sun and waves. Eat fresh seafood right on the beach, and if you brought your board, take the surf-bus that connects to the city’s most popular tourist areas.

Arriving alone and hungry in the Philippines, I checked into my hotel and immediately asked for a dinner recommendation. After some thought by the staff, I was directed to Zubuchon for some authentic Filipino food; but not just any food: Lechon. And not even just lechon, but what Anthony Bourdain suggested is the “best pig...ever.” This perfectly prepared pig keeps its moisture generously covered and insulated with a layer of pork belly fat. Unfortunately, for some reason, I was not able to purchase a piece of pork less than ½ kilo. So, that is what I ordered. Perhaps I should have given the menu a closer look and ordered from the selection of “Fast Meals” that appear to be better suited for one. Before I ran off with my ½ kilo of pig, the server suggested I also try a Kamias Shake which paired with the pork better than any wine pairing I have had with a meal! The tart, but not quite sour, beverage brought out all the nuances of the lechon. Back at my hotel, I was unable to stop myself from eating all ½ kilo of meat - and heading to bed that evening completely stuffed. Try the lechon in the Philippines. And make sure you have Zubuchon at least once!

The giant ferris wheel on the south bank of the Thames is made up of 32 futuristic glass capsules - all of which are sealed, air-conditioned and big enough to house 25 guests. Riding the attraction is effectively being stuck in a bubble, albeit one that offers 40km views in all directions (see if you can spot Windsor Castle in the farthest distance on a clear day). This is the wheel that never stops turning, and while views at the top are stunning, you won’t feel the ascent/descent: the Eye does one full rotation every 30 minutes, and turns so slowly passengers walk on and off at ground level. Curiously there is no capsule 13; since the number is thought to be bad luck, its been replaced in the lineup by the infamous no.33.

This tiny joint on the Big Island serves what many consider the planet’s best poke (raw-fish salad). In fact, Yelp ranked it No. 1 among America’s top 100 places to eat in 2014. Go traditional with just salt, limu kohu (seaweed), and inamona (a roasted-candlenut relish) for toppings. Or opt for a more contemporary twist with anything from onions to avocado aioli, perhaps paired with a side of crisp kimchi cucumbers. Be forewarned: This casual spot runs on island time so don’t expect exact adherence to business hours.

Full of wild scenery, fascinating history, and delicious local food, Loch Lomond & the Trossachs National Park is a Scottish treasure. At the center of the park is Loch Lomond, the largest body of freshwater in the U.K., featuring ample recreation (everything from kayaking and canoeing to jet-skiing), 30 islands (visit Inchconnachan in spring to see a blanket of bluebells), and miles of bonnie banks (for strolling in the shadow of Ben Lomond). Beyond the lake, the park is packed with interesting corners to explore, from the lush landscapes of the southern section to the sprawling glens and rocky peaks in the north. For the best views, cycle the challenging Loch Eck Loop, or hike the craggy Cobbler. Also worth seeking out are villages like Balmaha, national scenic areas such as Queen Elizabeth Forest Park, and more off-the-beaten-track areas like the Cowal Peninsula and Breadalbane.

Mexico City’s fun speakeasy shows no signs of stopping. Officially a membership club, ambitious gate-crashers (doll up and don’t be pushy; foreign accents not a liability) should look for a rather forlorn, seemingly late-night Calle Londres sandwich shop. Are those customers and employees real? Once you’ve talked your way through the air-lock-style door to the back room, you reach a genie’s bottle of a lounge, outfitted in sexy, disco style. Groups take booths and others sit at the bar where surprisingly friendly—and deeply knowledgeable—bartenders shake, stir, garnish, and ignite some of the city’s most showstopping haute cocktaillerie. They’re happy to make your usual, but why not let go a little, allowing mixologists to add their surprising touches? A winning combo of insiders-only and everybody’s-welcome. [Editor’s note: Go to the Hanky Panky Facebook page and send them a direct message. They’ll respond with the exact address and a reservation.]

Expect to be transported back to medieval times during your visit to Château de Chillon. More than 1,000 years old, the beguiling castle has inspired many poetic greats, none more so than Lord Byron, whose poem The Prisoner of Chillon was based on François Bonivard’s imprisonment. Travel across Lake Geneva on a paddle steam boat to arrive at the castle and note that the Rivera Pass, offered by most hotels, grants you half-price admission. Once inside, pick up an audio guide (available in English) and explore everything from cobblestone courtyards and eerie dungeons to secret passageways and castle walls.