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  • 24 Wharf St, Wellington, ON K0K 3L0, Canada
    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 19th-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.
  • Via Vittorio Emanuele Orlando, 3, 00185 Roma RM, Italy
    Opened by Carlo Ritz in 1894, the St. Regis belongs to a particular category of five-star hotels in Rome in which Old World glamour is alive and well. While the current trend in town is toward boutique hotels and converted townhouses, the St. Regis is palatial and uncompromisingly opulent. In the century (plus) since opening its doors on the crest of the Quirinal hill, the hotel has remained a beacon of luxury, and indeed many of the hotels on the nearby Via Veneto, Rome’s luxury hotel row, take their cues from this long-established pioneer.

    The entrance through the marble portico just off Piazza della Repubblica leads directly into a grand salon furnished with overstuffed chairs, chandeliers, and antiques. The grandeur continues in the rooms, where classic style and sophistication reign. Owing to its elite clientele, the hotel’s 23 suites come with 24-hour butler service, while the aficionado program is designed to provide exclusive access to sites and special experiences including road trips designed by the Ferrari racing team or helicopter rides to wine estates.
  • 50135 Settignano, Metropolitan City of Florence, Italy
    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.
  • Frigate Bay, St Kitts & Nevis
    A collection of rambling beach bars, The Strip on South Frigate Bay is the best “lime” on St. Kitts—a beach bash by day that transitions to an open-air dance party, moveable feast, and pub crawl by night. The area is within walking distance of the St. Kitts Marriott Resort, but it’s a popular nightlife destination for locals and visitors from all over the island. Don’t miss Mr. X’s Shiggidy Shack, the most famous bar on St. Kitts, where you can enjoy grilled lobster alongside an ever-changing lineup of live entertainment, from karaoke to fire-eaters. Also worth visiting are Vibes (St. Kitts’ closest thing to a sports bar), ChinChillas (for Mexican food), and The Dock Bar, which offers a more relaxed scene and, as its name suggests, its very own dock. Wherever you land, expect live bands and DJs to keep the dance floor hopping well into the wee hours. If you get tired, cool off and then rev up with a “Ting with a Sting,” a popular drink of local CSR rum mixed with grapefruit soda.
  • 600 F St, San Diego, CA 92101, USA
    At first glance, the lobby is the place to be at this boutique hotel in the Gaslamp Quarter. At check-in guests are offered a selection of local wine and beer—and again during happy hour. Under soaring ceilings supported by leather-wrapped pillars and surrounded by colorful art, you can sip and socialize. But don’t ignore the scene on the roof, either, where you’ll find a pool with oversized, floating pillows; fire pits with food and drink service; and views of the Coronado Bridge, Mount San Miguel, and the old and new architectural icons of downtown. In fact, the rooftop is so special, you may want to book the only accommodation in the 159-room hotel that grants you direct access to it: the Cabana Suite, where a private staircase leads to your own poolside cabana. On the other hand, if you’re traveling as a family, you may find that another option beats private rooftop access: the Star Suite, complete with three king-size beds, two of which form a custom-built bunk bed. Either way, expect ultra-modern furnishings paired with skyline views.
  • 403 N Crescent Dr, Beverly Hills, CA 90210, USA
    Up-and-coming starlets in the 1920s and ‘30s would have stayed at the Crescent. When the palm tree–lined art deco building opened in 1927, it was as lodgings for the budding actresses who’d just signed studio contracts and moved out to L.A. for their big breaks. They, too, sipped cocktails (after Prohibition ended, of course) and listened to jazz (probably not by a live band, though) in the intimate lounge and on the breezy terrace. It’s even just possible there was saltwater taffy at the front desk and a library stocked with an impressive collection of classic and contemporary literature and nonfiction. However, the walls might not have been adorned with paintings and photographs by some of the area’s top artists, and there definitely wasn’t 24-hour room service or iPod docks.

    After the studios moved on, and luxury designer shops and trendy restaurants moved in, the Crescent turned into a cozy, quirky boutique hotel known for its prime location, affordable rates, and bend-over-backward service. These things won’t change.
  • Adare, Co. Limerick
    With its lanes of thatched-roof, old-Irish bungalows fronted by flowering gardens, lovely little Adare is beloved by a certain subset of Irish grannies as the prettiest village in Ireland. It’s easy to see why: An hour south of Shannon Airport on the river Maigue, the town has charm to spare (although it’s quite touristy these days). Adare’s crown jewel is east of the town center, where the 19th-century Adare Manor lies with its pergola-covered stone walls, turrets, and gables on 840 acres of manicured gardens and wild woodlands.

    Designed in grand Gothic Revival style and completed in 1862, the manor took 30 years to build—and provided valuable industry for villagers during the potato famine years. Inside, it’s a castle with some quirks: 365 stained-glass windows and 52 chimneys, for instance, for each day and week of the year. Rooms have four-poster or carved-mahogany beds, sitting areas, and semi-chintzy drapes.
  • Saint Mary's Street
    What’s a roti? The simple answer is the ultimate comfort meal of curry wrapped in a thin dough—borrowed from India and perfected in Trinidad and Tobago. You have to understand — making roti is not an easy task. Like many other traditional Caribbean foods, it takes a lot of time and effort to make something this comfortingly delicious… And perhaps those hours of anticipation actually added a little something to the flavors when you finally got the finished, hot roti in between your hands. It starts with the “skin” or roti (officially, only the skin is called roti, but in the Caribbean, we apply the name to the whole package). This is where a roti becomes a success, or literally falls apart. Any time you buy a roti, this is always the thing most people comment on. “Skin’s too thin.” “Skin’s too thick.” “Skin’s too dry.” Etc. The roti skin has to be just right, or the whole thing will fail. My favorite type of skin is dhalpuri which is just what you’ll find at Roti King — now just ask them to fill it with goat, chicken, or shrimp and you in business!
  • 335 Bowery, New York, NY 10003, USA
    Tastemakers and A-listers abound at this East Village mainstay, which celebrated its 10-year anniversary in 2017. Travelers feel like insiders the moment they slip through the door, thanks to over-the-top service, celeb sightings, and a lobby design that recalls salon parties of bygone eras. The cool factor only continues upon check-in, when guests receive metal room keys linked to lavish, oversized red tassels. Each of the 135 rooms offers visitors a mix of lived-in comfort and luxurious detail, with everything from mohair-upholstered chairs, Turkish Oushak rugs, and hardwood floors to iPod stereos, hi-def televisions, and marble bathrooms with deep-soaking tubs. When hunger hits, guests can head downstairs for authentic Italian plates at Gemma and a nightcap at the Lobby Bar, a lower Manhattan staple known for its timeless ambiance and clever riffs on cocktail classics.
  • 3927 Rue Saint-Denis, Montréal, QC H2W 2M4, Canada
    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.
  • Lake Matheson, West Coast 7886, New Zealand
    Lake Matheson is a magical little spot near Fox Glacier. It’s a great place to take a walk at sunset, before enjoying dinner and some local wine at the Matheson Cafe. On a clear day, the reflection in the lake proudly displays all the reasons to be in love with the Westland National Park region of New Zealand, while the rugged peaks of Mount Tasman and Mount Cook rise out of the mountain range. This is glacier country at its best. The lack of wind—the lake is set within the dense rain forest—means Lake Matheson’s surface is calm and still. The reflection photo opportunities have made this lake the most photographed body of water in New Zealand (and that is saying something). The walk around the lake takes about an hour and a half, and you have three viewing platforms offering exceptional perspectives along the way. Hit the trail just before sunset and have a glass of Otago Pinot Noir at the cafe while you watch the sun set over those mountains. The cafe opens at 5:30 p.m. and I’d suggest the mushroom risotto.
  • 875 N Michigan Ave, Chicago, IL 60611, USA
    Every city has a building with great views and Chicago’s most famous is the 103rd floor of the Willis Tower. But a little Chicago secret is that the John Hancock building has better views and their Signature Lounge on the 96th floor has free admission so you can enjoy a cocktail while you take in the sights! My favorite time to visit is late afternoon for a happy hour Old Fashioned while the sun sets and the Chicago lights start to sparkle. It’s a great place to take visitors, it’s a great place for tourists, it’s a great place to start or end an evening but I wouldn’t bother with the food, which is overpriced for the quality and selection. The drinks are pricey but the view is truly worth it.
  • 1 Redonda Bay, Tola, Nicaragua
    Seclusion and tranquility are the new forms of luxury in a world that is so accessible and plugged in. Aqua Wellness Resort successfully marries contemporary luxury accommodations with serene surroundings, providing a memorable and rejuvenating experience for travelers. Accessible by a two-and-a-half-hour drive or 40-minute helicopter ride from Nicaragua’s international airport in Managua, Aqua offers peace and privacy so that you can enjoy the beautifully wild landscape of Nicaragua’s Pacific “Emerald Coast.” 24 Tree Houses accommodating 50 luxurious villas and suites dot Aqua’s forested hillside, which overlooks a private, white sandy beach.
  • 29450 Valley of Fire Hwy, Overton, NV 89040, USA
    Valley of Fire is the oldest state park in Nevada, and a great place to see 3,000-year-old Indian petroglyphs and explore the red sandstone formations created during the age of the dinosaurs. Bring your camera to photograph the landscape while hiking this rocky landscape formed over 150 million years ago. The red sandstone gives off an incredible light, which makes the grey rocks nearby appear turquoise. Great place to camp while watching incredible sunrises and sunsets! Photographers will go crazy for this place, especially in spring, when a variety of wild flowers bloom. Skip the Las Vegas strip and head straight to this magical place!
  • 2121 McKinney Ave, Dallas, TX 75201, USA
    When the Ritz-Carlton Dallas opened in 2007, it didn’t have to go far to find a star chef for its gourmet restaurant. Dubbed the father of Southwestern cuisine, and the author of notable cookbooks like The Texas Food Bible, Dean Fearing had helped earn the restaurant at the Mansion on Turtle Creek numerous awards during his two decades there—but was now up to the challenge of opening his own place. A decade-plus later, the James Beard Award–winning Fearing continues to be a favorite for its Southwestern-accented American menus crafted with regional products.