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You know how they say that Montreal is a happy mixture of North America and Europe? Well, if there’s one place in the city that’s truly unique, and not influenced by any other colony, it’s Plateau Mont-Royal. Located just a few minutes north of downtown, this neighborhood is lively, colorful, and somewhat eclectic. Here young families, hipsters, and fancy folk mingle together in harmony. In this iconic area you will find everything you need—from French bistros, typical French-Canadian brunch joints, clothing stores, and fine groceries. Nothing is expensive as such, but restraint is in order, because absolutely everything is enthralling!

True to its name, this is an old bar, with Victorian-style décor, stained glass, art nouveau lamps, and red velvet sofas. You can find a long list of cocktails, as the manager has history in the Miami cruise ship industry. From the food menu, try the Old Vic steak—or some toast or a sandwich, if you want something lighter. There is a button to call the waiter and another one to regulate the light intensity.

Dating to 1521, the Cathedral of San Juan Bautista isn’t just one of the oldest buildings in San Juan—it’s the second-oldest cathedral in all of the Americas. Go inside to see the tomb of Spanish explorer Ponce de León, who founded the first settlement on Puerto Rico and in 1509 was named the island’s first governor. The remains of St. Pio, a Roman martyr, can also be seen in the cathedral—the saint’s mummy has been displayed here in a glass box since 1862.

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.

Set down a small alley just a few meters from Piazza San Lorenzo, the art gallery Il Vicolo is a lovely spot to browse, and purchase, contemporary art in the ancient city. One of the oldest galleries in town, Il Vicolo routinely changes their artistic focus - thus one can come back often for pieces and exhibits from new, well-followed, and even young emerging artists.

Whether you sit on the benches out front and people watch or stroll along Main Road and window shop, exploring the village of Kalk Bay on a summer’s day is so much better with a cone in hand.The Ice Cafe is one of the oldest ice cream parlors in Cape Town. The flavors are robust and all natural, the texture is perfectly creamy (like gelato). Cones are not overpriced like some other newer options in town.

Like to have a meal with historic spirits? Visit the oldest tavern in MA. and one of the most historic watering holes in America. First erected in 1780 in Charlestown, George Washington dropped in for refreshments and Paul Revere counted it among his favorites. Featuring traditional tavern fare for lunch and dinner, it’s a great pit stop after burning up calories climbing the Bunker Hill Monument just up the street.

Serene. That’s how I would describe the pool at the Lone Pine Hotel in Penang, Malaysia. This lovely boutique hotel is one of the oldest hotels in Penang, established in 1948. Recent renovations have made it into a charming ‘modern classic’ beach getaway. It’s under the management of the exclusive E and O Hotel. So you can expect beautiful rooms and good service, but at a more affordable price.

Singapore may not have bicycle lanes on its roads, but the country does have a wonderful and growing network of bike-friendly asphalt paths along its many canals and rivers that are sometimes joined up with pathways in parks and along old rail corridors (in Singapore, they’re called park connectors). An easy 3-mile round-trip stretch to sample runs along the Singapore River. Join the riverside pathway just off Zion Road near the Great World City shopping mall—you can rent your chariot nearby from Bike Connect, at 23 Hoot Kiam Road—or grab a two-wheeler from the now ubiquitous bike-share steeds parked everywhere. Pedal all the way to the old shophouses of Boat Quay where the river empties into Marina Bay and then the South China Sea at the heart of Singapore’s colonial core. From there, get a glimpse of the grand Fullerton Hotel (once the national post office), the Asian Civilisations Museum (originally intended to be the city’s courthouse), and several historic bridges.

On this rainy afternoon that I visited, Kitchener’s had the DJ on the decks mixing up a storm inside the venue, with patrons being able to browse the goods with their drinks in hand all the while being able to do a little boogie! Whether it’s on the weekend or during the week, Kitchener’s does get very full, but is always good fun! On the weekend’s the bar transforms into a bustling, bar/market with jewellery, vintage books, clothes and more on sale. A cool fact about Kitchener’s: It has the honour of being the second oldest bar in Johannesburg. Check out their full list of events on their Facebook page

This beautiful square is one the city’s oldest; set in Le Marais, it’s surrounded by grand houses and an arched walkway lined with galleries and quaint cafés. At Number 6, you’ll find the former home of Victor Hugo, author of “The Hunchback of Notre-Dame.” The park at its center is a popular place to gather al fresco in the warm weather.

On a quiet residential street one block from the popular vintage shops, bars, and restaurants of Milwaukee Avenue, the Wicker Park Inn is one of the best values in Chicago, attracting an eclectic clientele of older couples, families who book the whole place for weddings and other special occasions, and young travelers eager to live like a local amid the vibrant culture of the Wicker Park and Bucktown neighborhoods.

More than worth a visit if you’re in the Gaslamp Quarter, Neighborhood features healthy food for everyone from the meat lover to the gluten avoider. Guests will also find around 27 local brews on tap and many more kinds of bottled beer. The vibe here is cozy, with plenty of shared seating by large, open windows. Note: it can get busy during peak hours, so it’s best to visit just before or after the usual lunch and dinner times.

Located along a stretch of coastline that’s sometimes called the birthplace of jerk cuisine, the Boston Bay Jerk Center is hard to miss. Various meats are cook on open pits using a technique that may explain why jerk never tastes so good at home: Uncured pimento logs are placed over a bed of hot coals, and the meat is laid directly on the green logs. The whole operation is then covered up by a sheet of corrugated zinc and cooked until it’s black on the outside and tender underneath. You can place your order by the quarter, half, or full pound. Don’t forget to add jerk sauce, which you can also buy by the bottle as a souvenir.

Welcome to the vagina island, no joke (the rough English translation of the word Huahine is vagina). And although no one knows exactly where the name originated, historians think it has to do with the important role women played in the island’s history. Comprised of two islands – the more developed Huahine Nui (Big Huahine) to the north, and Huahine Iti (Little Huahine) to the south – there isn’t a lot to do here, but the unpretentious and relatively sleepy vibe appeals to budget travelers and surfers, as Huahine has some of the cheapest beds and best breaks in all of French Polynesia. It is also home to untouched beaches, isolated coves, enchanted azure lagoons and the most extensive complex of pre-European marae in French Polynesia. It also has a noticeable lack of luxury resorts, making it still feel like a Robinson Crusoe style getaway. Some of the most consistent and best surf in French Polynesia is found off Huahine’s shores, but local surfers can be very possessive, so make sure you check with them before hitting up their turn. This is also not the place for novices, as the left and right reef breaks can chew you up pretty badly. Huahine is also home to some great dive spots, including a canyon where you can see barracuda, jackfish, rays and sharks. For snorkeling head to Fare, which has a pretty sand beach just north of town and a wide, translucent lagoon that drops off quickly for excellent snorkeling around coral and through schools of multi-hued fish.