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Ontario has another wine destination, Prince Edward County, affectionately named “The County.” This cluster of towns, about 2.5 hours east of Toronto, is home to some of Ontario’s best wineries. But never was there a great place to stay until summer 2015 when Jeff Stober, the hotelier behind Toronto’s stylish Drake Hotel, opened a rural clone, the Drake Devonshire. It’s the ideal retreat for travelers wanting their Drake by Lake Ontario. Once a 19^th-century foundry, the building is now a contemporary farmhouse-cottage, decked out with 11 individually-designed hotel rooms and two suites in the quaint town of Wellington. The property offers coziness all year round in the communal living room and out back over a lakeside fire pit and s’mores. Guests can hang in the barnlike Pavilion for musical performances, sommelier seminars, seasonal events, or just to gawk at the floor-to-ceiling mural by Brooklyn artist FAILE. It doesn’t hurt that Sandbanks Provincial Park—known for its 60-foot sand dunes—is practically the backyard of the Drake Dev.

The Belmond Villa San Michele knows something about history. Michelangelo designed its facade, Franciscan monks tended its gardens, and Brigitte Bardot stayed here. But, like any elegant host, it’s not brash about its pedigree. Manicured Italian gardens—designed by 15th-century friars—beckon you for sun-soaked strolls. The colonnaded loggia is a pleasant place for a sunset aperitivo or candlelit dinner, especially with a view of Florence and the Arno Valley. The hotel’s expansive rooms are already decked out in the most tasteful, almost understated interpretation of Renaissance luxury—terra-cotta tile floors, heavy wood furnishings, just a dash of red velvet, and plenty of cream-colored walls—and then the panoramic views, original frescoes, and modern Carrara marble bathrooms steal the show. There’s a real-deal cooking school, where the chef actually works with each person in hands-on preparations—no demonstrations-only here. Other perks include the hillside pool, the concierge service that can get you into the Uffizi outside of operating hours, and, from the Loggia Restaurant, a view of the ancient Roman road that once connected Florence to Fiesole.

Mountain Equestrian Trails (MET) Outfitter & Lodge exemplifies the best of family-run ecotourism. Anywhere with an address like “Mile 8” off a pot-holed dirt road in Belize’s jungle is guaranteed to be an off the beaten path experience. The car ride in is a bumpy ride but makes arriving a true reward. The small staff of horse-riding adventurers embraces you like family and personalizes your stay with their endless knowledge of the land, animals, history, surroundings and active excursions. Toucans pose in the tree tops, parrots dart through the lush surroundings and horses graze nearby, ready for guests to ride them to nearby swimming holes, waterfalls and caves. The rooms are cozy, kerosene-lit Spanish bungalows topped with palm-thatched roofs and the Cantina serves as the central hang-out spot where farm-fresh meals and drinks are served. The Cantina is also the only place on the property with electricity and Wi-Fi so you’re not completely off the grid, but with views like the one pictured, you could care less even if you were.

Ultra-modern Hotel Habita sits on upscale avenue Presidente Masaryk, in the midst of the Polanco’s fine restaurants and shops. Opened in 2000 and renovated in 2012, the hotel, which looks like a glass cube, continues to attract travelers who appreciate its sleek design and superb location. Rooms are typical of Grupo Habita hotels-spare and uncluttered, with luxurious toiletries and high-tech amenities, like flat-screen TVs and free Wi-Fi. The staff is accommodating and will help guests with everything from transportation recommendations to securing reservations at top nearby restaurants, such as Biko, Pujol, and Quintonil. All three appeared on the 2015 “Latin America’s 50 Best Restaurants” list.

Mérida’s many historic plazas are jam packed with open air event throughout the year. Popular with tourists and locals alike is Yucatecan “Jarana”, a traditional form of dance accompanied by live music. One of the best places to see the show is at “Serenata Yucateca”, a free event each Thursday in the newly restored Plaza Santa Lucía, a traditional square just four blocks from the main Centro plaza. The musicians, singers and dancing “mestizos”, decked out in their colorful costumes begin the show at 9 PM, as they have for the last 40 years. There are plenty of benches to sit to enjoy the show. Also, with restaurants and bars spilling out on the sidewalk, its a great way to catch a dinner and show. Santa Lucía in not just a park, it is also the name of the neighborhood that has come alive since the recent renovation. With traditional cafes, restaurants and shops such as La Chaya Maya and Coqui Coqui Perfumerie, it is fast becoming the “it” place to be in downtown Mérida. Many colonial houses with a private pools are available to rent in Santa Lucia and in the surroundings so you can close the action. (Images courtesy of Merida.gob.mx and aany.org)

Charleston’s French Quarter didn’t earn its title until the 1970s, when a group of preservationists started touting the area’s historic concentration of French Huguenots to protect buildings in danger of demolition. Opened in 2002, the French Quarter Inn took its neighborhood’s name and used it as inspiration for the hotel’s opulent decor and signature services. Guests arrive to an atrium with an elaborate wrought-iron staircase that rises in a spiral from the ground level and is topped with a large skylight. Champagne awaits guests upon check-in, and the rooms are decorated in vibrant shades of red, gold, and black, with toile bedspreads and damask upholstered furniture.

While it may not have the historic character of many Charleston properties, the French Quarter Inn provides all the amenities travelers could require: a continental breakfast each morning, bike rentals for cruising around town, and nightly wine-and-cheese receptions.

Owned by Terry Kaljo—a former model and founder of the Contemporary Hotels collection of upscale rental homes and villas—the Medusa Boutique Hotel offers 18 unique accommodations in Darlinghurst, an eclectic area and the epicenter of Sydney’s gay community. The 19th-century home is filled with wacky touches, from red Alice in Wonderland–style carpeting that runs up the grand staircase to pastel-pink walls studded with maple leaves in the entryway. The midcentury-modern rooms—with their retro primary colors, geometric patterns, and vintage chaises longues—attract fashion, media, and design professionals looking to get beneath the surface of one of Sydney’s liveliest neighborhoods. But there’s still the opportunity to relax, as guests can settle in next to the fireplace in the lobby to read the newspaper, enjoy a complimentary pastry, or make new friends. Longtime staff members offer the kind of local knowledge and personal attention that keeps guests coming back.

The sprawling contemporary museum, MASS MoCA, is responsible for bringing North Adams to life, and offers some of the most cutting edge art around. Xu Bing’s Tobacco Project {above} is made from over half a million cigarettes arranged to mimic a tiger skin rug. It makes a thought provoking statement on the global tobacco trade, luxury and colonialism, and is typical of the installations you will see there. The complex also hosts a variety of musical events including dance and films. Luckily Split, the in house restaurant has coffee, treats and tasty lunches.

You haven’t quite experienced the most authentic Reggae concert in Jamaica until you’ve been to Rebel Salute. While Sumfest gets all the press and is more commercialized, Rebel Salute—held every January—is Jamaica’s largest strictly-Reggae all-night show, headlining every single big Reggae music name you can think of. Now held on the north coast, on the picturesque grounds of Grizzly’s Plantation Cove, this well organized, alcohol-free event welcomes everyone from families to couples. Camp out by bringing your lawn chairs and blankets to indulge in the best of Reggae all night long, under the starry nights of the south. Food and soft drink vendors are present, of course, as are souvenir sellers. Tour operators do arrange group round trips to the event—inquire with Clive’s Transport--and hotels near the venue offer deals.

Chilean wine is having a moment, with vintners discovering the myriad terroirs in the country spanning over 10 latitudes from the Pacific to the Andes--with over two dozen grape varietals. Many of the most avant-garde projects are small producers making garage or even underground wines alongside the reference wines. Enter Santiago Wine Club. The owners, two wine-loving friends (one French, one Chilean), teamed up to bring these inspiring wines to their loyal patrons in Barrio Lastarria. Arranged by valley, their are obscure, fun, serious wines for everyone. Owners are usually at the store and know their wines well. Perfect for any wine lover or drinker to take a bottle home--or drink while in town. Rosal 386, almost corner Victoria Subercaseux, Barrio Lastarria Phone: 56 (2) 2632 6596

Intricate textiles woven on looms handed down through generations. An array of laurel, olive, and lavender bath products and the hammered bowls to hold them. Silk shawls with which to drape the color of the Aegean in a graceful arc below bare shoulders. All organic and produced locally, with the specific intent of preserving a dying art. Jennifer’s Hamam works with traditional Turkish weavers to produce luxuriously looped Turkish towels, flat-woven pestamels (the towels and wraps used in hamams, similar to a sarong), and fine silks woven from hand-spun thread. Looms are passed from one generation to the next. New designs evolve over time. Part entrepreneur and part preservationist, Jennifer and her staff are generous with their knowledge and delight in sharing their affordable luxuries. Wander, shop, and emerge enlightened. Accessibility: A wheeled walker can easily maneuver the main path of the Arasta Bazaar.

Not far from Kelowna driving along Lakeshore Drive and passing aging vines of lush with grapes for harvesting, sits the goats of the Camelis Alpine Goat Cheese Artisan. Exiting the vehicle you hear the playful singing of goats in the distance sensing the arrival of someone new. On a fall day the blue Okanagan Lake and the autumn colours create a visually robust cornucopia and you can’t do anything but drink it in. The gift shop is similar to an old fashioned western candy store as the entire building is a converted farmhouse. To my right is a display of local olive oils and vinegars. To my left is an enticing display of house made goat cheese gelato and before me is an array of goat cheeses that I didn’t know existed. From goat cheese with delicious ribbons of mouldy blue, a goat cheese that mimics a camembert and a yogurt cheese ideal for spreading there is a cheese to match all tastes. Open from May 1st - October 31st.

In a remote spot off Vancouver Island in British Columbia, surrounded by rain forest, mountains, and beaches, the Clayoquot Wilderness Retreat first opened in 1998 as an overnight floating lodge experience; since then, it has grown into a luxury tent retreat. While the camp has a rugged outpost atmosphere, with huge stone fireplaces and a long wooden cookhouse, it’s an outpost with every possible luxury: from white linen tablecloths and polished silverware to soft comforters and high-thread-count bedding.

Visiting this cheese shop was like touring Costco during Christmas. Samples, my friends. Samples. I’ve never tried so many different cheeses in my entire life, and I’m certain I left this little shop lactose intolerant. And I would do it over in a heartbeat. Ireland‘s cheese scene really is something to behold, and this is the place to stock up your picnic basket prior to touring the Dingle Peninsula. I’m a fan of the heavy, funky stuff - the more mold the better - but I’m sure you’ll find something to suit your fancy under this roof. Don’t forget the bread.

When Garden Village Bled opened in 2014 it took the concept of glamping to an entirely new level. Guests can choose to stay in glamping tents (some come with their own hot tubs), treehouses or pier tents. Treehouses are great for families as they come with kitchenettes, hammocks, and two bedrooms. The pier tents are the most basic, but are still done up with electricity, and super comfy beds. Each tent is set on a pier on the river so guests can fish right from their deck and the chef will cook up their day’s catch. I loved falling asleep to the soft rumble of the river below.