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While hiking in Cape Town, there are plenty of moments when you’ll stop for a water break, wipe the sweat from your brow, and ignore those voices inside yourself saying you can’t possibly take another uphill step. This moment is fleeting, however, and always superseded by the lasting memories of when you feel like you’re on top of the world at the end of your hike. Silvermine Nature Reserve is 20 minutes from the city center and the part of Table Mountain National Park that covers the Cape Peninsula near Kalk Bay and Muizenberg. The Echo Valley hike can be approached from the Silvermine entrance on top of Ou Kaapse Weg (one way), or, from the entrance on Boyes Drive in Kalk Bay.

Wilensky’s is sort of an institution in the Mile End. Family-owned since its opening in 1932, the place is famous for its extremely cheap snacks, no-nonsense approach, and retro decor. Pressed tin ceiling, Kik Cola clock, ring-up cash register, old-fashioned soda fountain—this place sometimes feels like a time warp or, at the very least, a museum. Perhaps what makes Wilensky’s so special is, incidentally, the Special ($3.90): “All-beef salami with all-beef baloney grilled to mouth-watering perfection on a tasty roll with a hint of mustard.” But don’t try to change anything in it—the owner, Ruth, will not have it. The Special is what it is, and no amount of money will make Ruth change it. Hell, she even wrote a poem about it: When ordering a Special, you should know a thing or two. It is always served with mustard; it is never cut in two. Don’t ask us why; just understand that this is nothing new. This is the way that it’s been done since 1932. Amen to that.

L’Express, on rue St-Denis in the Plateau Mont-Royal neighborhood, opened in 1980 and has about it the air of a beloved institution. Indeed, with its timeless style, it feels even older than it is. This popular spot serves classic renditions of bistro fare—steak tartare, bone marrow, onion soup—into the early morning hours (2 a.m. except for Sundays, when it closes at 1 a.m.). When the kitchen ventures into new territory, the results are impressive. The spaghetti with mushrooms is unconventional in its presentation (topped with a healthy serving of arugula)—one of those dishes you try on the road and then want to re-create at home. Reservations recommended.

Rustic elegance is the order of the day at La Champagnerie, a champagne-only bar in Old Montreal. Between the delicious cocktails, heaven-sent food, and exposed brick walls of this historic building, the drinking experience will be memorable. The menu features over 50 different brands of bubbly (including real champagne, cava, and prosecco) and a very entertaining sabering act, as well as brie poutine and oysters. Contrary to popular belief, la Champagnerie isn’t that expensive. Yes, there is the odd $500+ bottle, but visitors can easily enjoy a meal and a cocktail or two without needing to remortgage their house. A very nice way to spend an evening, if you ask me—champagne, Old Montreal, and good music. Santé!

Ask any Montrealer the question “Which is the fanciest restaurant in town?” and chances are Toqué! will be a frequent answer. Indeed, quite fancy. But also quite expensive. Luckily, chef Charles-Antoine Crête, once mentored by Toqué’s Normand Laprise, decided that a more accessible and younger version of the famous restaurant would fit perfectly well with the new Place des Festivals—in style, location, and ambience. And he wasn’t wrong. I always go for the beef tartare, and not once have I been disappointed. The menu changes according to the season, but there is a constancy in quality, regardless of the time of the year. This is definitely the best way to get a taste of Montreal‘s finest, sans the waiting list and the steep check.

The 6km range of mountains jutting out on the Atlantic Coast of Table Mountain are known as the “Twelve Apostles”. The 18 peaks located between Camps Bay and Llandudno make for a very scenic route by which you can travel from Cape Town to Hout Bay. If you have time, continue on all the way down to the Cape Peninsula. The 12 Apostles Hotel, an exclusive, five-star property, is nestled in these mountains. Dine at the on-site restaurant, Azure, where approximately 95% of their ingredients are sourced from the Western Cape. If a meal or overnight stay is beyond the reach of your budget, you can always stop by for a drink or book a spot at their afternoon “Tea by the Sea”.

Historic Santo Domingo offers a unique look at how the New World was settled in the years following Christopher Columbus’s arrival in the Caribbean on his first voyage in 1492, as well as subsequent expeditions. The Colonial Zone sits along the Ozama River, where the settlement’s original layout, walls, forts and other buildings remain much as they were 500 years ago. With its wealth of colonial architecture, the area has not surprisingly been recognized by UNESCO as a World Heritage Site. Among the historic buildings is the first cathedral built in the Americas, the Basilica Cathedral of Santa María la Menor (also known as the Catedral Primada de América, recognizing its historic significance). The ornate church once housed the remains of Christopher Columbus until they were moved to the Columbus Lighthouse, in the eastern part of the city.

Former British prime minister Harold Wilson, who loved the Isles of Scilly and visited every summer (his wife, Lady Wilson, now 100, still does), is buried at the pretty Old Town Church in its atmospheric graveyard. The grave is modest compared to the grander tombs belonging to distinguished Scilly families, but not nearly as modest as the Wilsons’ nearby summer house, which is inconceivably tiny for a residence of one of Britain’s most important 20th-century statesmen.

Comprised of just 10 suites with distinctly different designs, Palácio Belmonte feels more like a dream vacation home than a hotel. The vibe is spot on, given the backstory: A Frenchman traveled to Lisbon looking for a vacation home in the Portuguese capital. He first saw the building from a taxi and thought to himself, “It has nine windows, just like my home in France. I’ll buy it.” It wasn’t until after purchasing the property that he actually set foot inside and saw just how enormous it was—far too large for him and his family. Thus, he set about remodeling the building (which was originally owned by a noble family in the 1400s) with the notion of converting it into a space for visitors.

As you look at the chair, the vintage country-style fabrics will initially catch your eye, but it’s the suitcase frame that will make you do a double take. To Katie Thompson, the fit between old and new only seems natural. A graduate of the Design Time School of Interior Design in Cape Town, she’s been hoarding old housewares like suitcases, telephones, and typewriters and recycling them into functional pieces of furniture for years. Now that the Recreate showroom has moved into Katie’s original workspace on Stow Street in Salt River, travelers have a unique opportunity to see some of her pieces in development while shopping. You can also grab a cup of coffee and sit for a moment on the front patio before heading onwards to explore the rest of the Woodstock and Salt River neighborhood.

Castle Ho’s motto, the owner of lovely boutique 1861, is quite simple. “Women who love being women and dressing the part.” Such is the premise of her work, and it definitely transposes into her boutique. The store is decorated in what seems to be a vintage fashionista’s dream: airy space, high ceilings,Vvictorian inspiration, and soft eggshell, champagne and pastel pink hues everywhere. No boys allowed! The multi-brand store focuses on feminine, timeless pieces first and foremost, and incorporates up-and-coming designers into the mix, like UK-based Emily and Finn and Torontonians Pink Martini, along with Montrealers lines Coccolily and Arti Gogna. Don’t be fooled by the perfect, fairy-tale decor; the prices are more than fair and very few things are over $100 in the store. Guilt-free, stylish shopping? I like.

Many friendly squirrels will greet you while walking through the Company’s Garden, a park and heritage site located in the heart of Cape Town’s City Bowl. This garden, along with Kirstenbosch and Arderne, are the most beautiful green spaces with historical significance in the Western Cape. These particular gardens date back to the 1650’s, when the Dutch utilized the natural spring water running down from Table Mountain to establish a small area for agriculture. Now, City Parks is re-establishing part of the garden as an educational tool. You can bring a picnic or grab a bite at the small Garden Tea Room. There are several museums set on the periphery of the garden, including two of the best rainy day museums: the South African National Gallery and Iziko South Africa Museum & Planetarium.

The Bonsecours Market is hard to miss, whether you are walking around Montréal’s historic center or looking at the skyline from the harbor. A silver dome caps the long building, which dates from 1844 and was modeled on Dublin’s Customs House. It looks more like a stately civic building than a market, and in fact it was Montréal’s city hall for a while, as well as the seat of Canada‘s parliament for one session. After serving as the central market of the city for nearly a century, it closed in 1963 and was largely abandoned until 1992, when it reopened as the home of a visitors’ center for Montréal’s 350th anniversary. Today it houses a dozen or so boutiques featuring works by local designers, as well as a few restaurants that make for good pit stops on a day of sightseeing.

As if the Montreal restaurant scene weren’t exciting enough, 125 restaurants decided to come up with a special fall menu and draw people out of their houses in defiance of the weather. The concept behind Restaurant Week is fairly simple but oh-so-fantastic: 125 restaurants, one pre-set menu, and 3 price points ($19, $29, or $39 per head). This is a great way for Montrealers to experience restaurants that they wouldn’t be able to afford otherwise, and a way to discover new flavors. Make sure to look at the event’s website to consult the menus and pick your favorites. Reservations are strongly recommended. Also good to know: Many restaurants offer a special $19 menu for late-night orders, after 9:30pm. Bon appétit!

The Lantern Festival is without a doubt my favorite festival—ever, in the world. I’m not even sure why. It’s not star-studded. It’s not particularly big. It’s not in the warmest conditions. But damn it if it’s not the prettiest thing. The pathways of the Chinese Gardens are lit up at nightfall, illuminating hundreds of lanterns scattered around the pond. Some are animal-shaped, others are human-shaped, and together they create this amazing scenery that seems to have traveled halfway across the world. Which isn’t that far from the truth, technically. The lanterns are designed by Chinese artists in China and assembled in Montreal over the summer. If you are visiting Montreal in the fall, this event is a must-do. Until November 3rd at the Montreal Botanical Gardens.