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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.

The system of canals and chinampas (cultivated artificial islands fashioned from the area’s swampy soils) that has survived in the far-south neighborhood known as Xochilmilco once stretched all the way to the Centro. To this day, the community is known for its plant nurseries and vegetable gardens. These ancient landscapes now contribute to what has become one of the most singular pleasure gardens in the world, where visitors hire “gondoliers” to propel boats known as trajineras as they sail these channels in the company of floating mariachis and food vendors, partying teens, and extended families out for a picnic lunch. Since a tour is usually a four-hour-plus investment (it flies by), ask your oarsman to take you to Xochimilco’s more-rural precincts, where you’ll enjoy marvelous quiet, far from the madding crowd, in the company of cranes, curs, and picturesque cornfields.

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.

The Estate Whim Plantation Museum, billed as the only sugar plantation museum in the Virgin Islands, is set on magnificently landscaped grounds occupying 12 acres of what was formerly a 150-acre property. The restored early-18th-century buildings include a great house, fully restored windmill, and sugar-factory ruins that are open to visitors and can be toured alone or with a docent. Sugarcane still grows in one of the plantation gardens.

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.

I’m not sure exactly how Rainbow Beach got its name, though I wouldn’t be surprised if it actually had a lot to do with rain. The island’s most popular beach bar, especially on Sundays, is centrally located on St. Croix’s West Coast, some of the island’s tallest peaks and dense rainforest just a few miles behind it. Prevailing weather patterns, particularly during the summer months, make brief afternoon showers a fairly regular occurrence here. That doesn’t stop the party, though. Live bands play on and everyone keeps dancing. When you’re already wet from the sea and feeling the vibes, a little rain doesn’t hurt one bit.

The Fireside Lounge is unapologetically, gloriously tacky — which is why we love it. Tucked away inside the Peppermill Casino, the little corner bar can be a bit hard to find, so it’s usually less busy. The banquette seats around the water-filled firepit (imagine a hot tub with an Olympic torch stuck in the middle) get snapped up first, but the cozy booth seats have individual TV screens playing music videos. This is the kind of place where you can, and should, order a drink served in a fishbowl-sized glass with gummi worms hanging over the side. Happy hour is M-F from 4-7 pm and features free shrimp cocktails with your drink purchase, and there are late-night specials after midnight.

As a former Renoite, I now get to enjoy playing tourist when I return, which includes staying at a hotel-casino. For my money, the Atlantis is one of the best choices in town. It’s located a bit south of downtown, very close to the aiport and far away from the traffic chaos that festival weekends can bring. The decor theme is a surreal fantasy undersea wonderland, as befits the Atlantean name. Toucan Charlie’s is my favorite hotel buffet, setting out a particularly extravagant spread for holiday brunches and dinners. Guests get full access to the tropical-themed indoor atrium pool, hot tub, and outdoor pools. They’ve even made the skyway to the parking lot an attraction, packed with video slots, a sushi bar, and an oyster bar. As shown here, however, the hotel’s rooms are understated and peaceful, far enough from the noisy racket of the main casino floor to get a good night’s sleep.

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.

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!

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.

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.