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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.
  • Lower Nob Hill, San Francisco, CA, USA
    Bourbon and Branch is a traditional speakeasy. Their 8 house rules—hushed voices and no cell phones among them—encourage neighborly conversation in a very relaxed setting. It’s a great way to meet people if you’re traveling alone as well. There is a binder’s worth of libations here that are each expertly prepared by resident ‘mixologists.’ Don’t forget the password—they’ll give it to you when you make a reservation. It’s all part of the fun!
  • 35 E 21st St, New York, NY 10010, USA
    In October 2014, Chef Enrique Olvera opened his much-anticipated New York restaurant Cosme, which offers an inventive dining experience in the Flatiron District. The spacious restaurant is a short walk from Langham Place, Fifth Avenue, and features modern Mexican dishes with locally sourced ingredients and housemade tortillas. But guests should not come expecting standard chips and guacamole, Chef Olvera is known for utilizing creative and sometimes surprising ingredients in his dishes. Menu items include burrata, salsa verde and weeds, and occidental purple corn pozole, pork jowl, lettuce, radish, Mexican oregano. The eclectic menu items are meant to be shared, and certain Mexican specialties, like dried chiles, beans and heirloom corn are imported from Mexico. Chef Olvera’s Mexico City restaurant Pujol has gained world fame for his fresh take Mexican food, and Cosme offers more stellar options. The bar also pours a wide variety of mezcals and tequilas. Photo by T.Tseng/Flickr.
  • Av. Andrés García Lavín 334, San Antonio Cucul, 97116 Mérida, Yuc., Mexico
    Chef/owner Roberto Solís is widely considered one of Mexico’s best chefs—and Néctar deserves its reputation as one of the area’s top restaurants. The kitchen serves up traditional dishes from the area, all featuring local and seasonal ingredients so the menu changes depending on what’s being harvested around the Yucatán. But several local favorites are always available, including cochinita pibil(roast pork); relleno negro-stuffed turkey; and tikin xic (fish marinated in Achiote and sweet chile.
  • Yviri við Strond 14, Tórshavn 100, Faroe Islands
    The Faroe Islands’ newest boutique hotel, Hotel Havgrím sits on the shore just outside of Tórshavn. Formerly known as the Commodore’s House, the property has been lovingly restored to preserve its sense of history and connection to the sea—plaques with the names of all 21 commodores that have lived in the building since the 1950s hang in the lobby. The 14 airy rooms are equally inspired by the surrounding fjord, with a blue-green-and-white color scheme and sweeping ocean views. Some also have private terraces for taking in the scenery en plein air, as well as adjoining doors to create family suites. En-suite bathrooms include L’Occitane products and glass box showers that look out on the bedroom and the ocean beyond—just know that they don’t afford much privacy.

    Every morning, guests should head down to the charming breakfast room, where they can enjoy freshly baked Danish rye bread, smoked salmon, Icelandic skyr yogurt, and more while watching sheep graze on the farmland next door. Be sure to ask for the ginger shots, fresh-squeezed orange juice, and French press coffee, all of which—along with your breakfast—are included in your stay.
  • 946 Queen St E, Toronto, ON M4M 1J7, Canada
    Located in Leslieville in the East End, Swirl is in a small, converted apartment above a dog store in Leslieville. I love the decor here, from the tables made from doors or antique sewing machine bases to the artwork by local artists FAME. It’s a tiny place but it packs a punch. There’s no kitchen, so they have these amazing appetizers and desserts preserved in small Mason jars. Wine prices are affordable (and they have about three beers available now). On top of all of that, they host theme nights. For instance, you can watch Mad Men whilst sampling accurate cocktails from the era; board game nights; bubbly nights; and cinema Sundays. Suffice it to say, it’s one of my favorites. Warning: it’s tiny in here. Not meant for a big group, but perfect for a date.
  • 20 de Noviembre 512, Centro, 68000 Oaxaca, Oax., Mexico
    The 20 de Noviembre market has a variety of food stalls where you can sample many Oaxacan specialties, but carnivores flock to the one corridor that’s known as “El Pasillo de las Carnes Asadas” (the grilled meats aisle). Follow your nose to find it: smoke and the smell of meat grilling are thick in the air. You can select the raw meat that looks best to you and have it grilled to your specifications as you watch on. Find a spot at one of the long tables with benches and order salsa and guacamole to accompany your feast. Buy some tortillas from one of the passing vendors, and enjoy!
  • Gobernador Rafael Rebollar 94, San Miguel Chapultepec I Secc, 11850 Ciudad de México, CDMX, Mexico
    Three friends who found themselves thrown together in the New York of the 1990s—artist Gabriel Orozco, who has been featured at MoMA, the Pompidou Center, and the Tate Modern; Mónica Manzutto, who worked at the Marian Goodman Gallery; and José Kuri, who was completing an M.A. at Columbia—originally came up with the idea for what is now arguably Mexico’s most influential gallery. Kurimanzutto began with some ephemeral Colonia Roma events, often in nontraditional spaces. Today the gallery occupies a structure commissioned from renowned architect Alberto Kalach; its stable of artists includes Mexican creators of international stature like Dr. Lakra, Miguel Calderón, Carlos Amorales, and Damián Ortega, as well as global talents like Akram Zaatari, Apichatpong Weerasethakul, Anri Sala, Danh Vo, Jimmie Durham, Rirkrit Tiravanija, and Monika Sosnowska. Kurimanzutto’s shows—not to mention the openings—mark the pulse of the Mexico City arts scene.
  • 1055 Ashford Ave, San Juan, 00907, Puerto Rico
    Built in 1919, the Condado Vanderbilt Hotel is a Spanish Revival landmark, perched majestically above the Atlantic Ocean. From its opulent lobby to its luxurious guestrooms, the property fuses its storied past—it’s hosted everyone from European and Hollywood royalty to captains of industry—with distinctly modern amenities, making for one of San Juan’s best stays. Spread over a historic building and two towers, the 212 guestrooms feature stone-topped vanities, French windows, and ocean views, while the 107 suites include separate sitting and dining areas, L-shaped balconies, and 24-hour butler service. At the beach club and four pools, guests can also look forward to cabanas, personal butlers to bring refreshments, and assistance from a tanning and hydration specialist.

    When hunger strikes, the Vanderbilt is prepared with three different dining options. Hit Tacos & Tequila for escabeche pork tacos and Patron margaritas; Ola Oceanfront Bistro for Puerto Rican cuisine and water views; or, if you’re in the mood to splurge, 1919 Restaurant for sophisticated fare by Michelin-starred chef Juan Jose Cuevas. Also on-site is VC Lounge for expertly mixed cocktails, Marabar Martini Bar and Lounge for live jazz, Veritas Wine and Cognac Bar for rare vintages, and Avo Lounge for fine cigars. When you need to detox, head to the spa for indoor–outdoor treatments, rainforest showers, and hammam rituals.
  • Bremerholm 6, 1069 København, Denmark
    A five-star property in an old transformer station, Hotel Herman K brings industrial-chic style to the heart of Copenhagen. Much of the building’s raw, unpolished architecture has been preserved, lending the hotel an edgy vibe. A façade of dark bronze slats and large glass doors leads to the lobby, where a custom-designed artwork by Pio Diaz hangs from 40-foot ceilings. Down moody, dimly lit hallways, each of the 31 rooms and suites hides behind a black curtain, which is pulled aside for the duration of your stay. Inside, sleek furniture, soft carpets, and concrete walls contrast with white marble bathrooms, creating an altogether futuristic feeling. In fact, guests can even control the lights and sound from bed via panels in the headboard or steam their home media directly to the TV and speakers. If you need a break from all the technology, many rooms also include private balconies or terraces.

    Herman K comes courtesy of Brøchner Hotels (Denmark’s leading boutique hotel chain) and features many of the company’s signature amenities, including a healthy, organic breakfast and a “night cap hour” with complimentary drinks. Should guests want something more substantial, Herman K is also home to Roxie, a three-story restaurant from the team behind two-Michelin-starred Nordic restaurant Kadeau.
  • Budapest, Bródy Sándor u. 10, 1088 Hungary
    Founded in what was previously an artists’ residence, Brody House fittingly takes its name from Hungarian author Sándor Bródy. Each of the 11 air-conditioned rooms features a bohemian mix of upcycled furniture—think sofas with frames crafted from old shipping pallets and accent walls made with old wooden doors—and some have claw-foot tubs. The hotel is part of a larger effort that includes condo-style accommodations (Brody Apartments), a grand suburban villa (Brody Villa), and an art gallery (The Art Yard). However, the group’s best-known property is Brody Studios, a private-members club for the local arts communities featuring bars, workshops, and even a recording studio. All guests staying at Brody sites get free access to the space and its regular calendar of dance parties and literature- and art-related events as well as the occasional English-language comedy show.
  • Located on the north coast of Isla Robinson Crusoe, Cumberland Bay sits in the shadow of the volcanic peaks that form the spine of the island. Along the bay is the island’s only settlement, San Juan Bautista, a quiet town of fishermen living in modest homes. Below the sea here is an artifact of a moment when the island played a brief part on the global stage. The German SMS Dresden was launched in 1908 and took part in the Battle of the Falkland Islands in December 1914, during World War I. The ship then sought a safe harbor on Isla Robinson Crusoe, as Chile was neutral in the war. British ships, ignoring Chile’s neutrality, attacked the Dresden and its captain intentionally sunk the ship. It remains to this day resting on the bottom of Cumberland Bay.

  • 20100 Punta del Este, Maldonado Department, Uruguay
    Years before Punta del Este became a destination on the travel radar, Chilean artist Mario Irarrázabal installed one of the area’s most popular attractions, the public sculpture known as La Mano (The Hand). It’s also called Los Dedos (The Fingers), for its five fingers pushing up out of the sand on Playa Brava. Designed as part of an open-air sculpture exhibition in 1982, the fingers represent a warning, for the waters behind it tend to be rough. Many visitors are probably unaware of its meaning as they pause to pose for a photo with the hand.
  • Avenida General Rondizzoni
    The mercury during summer afternoons can hit 34C (or around 95F). How to stay cool during the hottest time of the day (4-6pm)? Besides seeking shade or air-conditioning, Santiaguinos seek solace in a traditional drink called “mote con huesillos.” Huesillos, sun-dried peaches, are cooked with water and a touch of sugar. The liquid and fruit are chilled and served with a scoop of toothy golden barley. Mote con huesillo is sold by vendors throughout downtown. More than a drink, it’s a satisfying, healthy snack.
  • 3141 Avda Isidora Goyenechea
    Among the sleek high-rise buildings of El Golf, right off the Plaza Peru, is Tiramisú (aka Santiago‘s best pizza). If you are yearning for an authentic, Italian pizza with thin crust, buffalo mozzarella, and primo ingredients pull up a chair. Always buzzing with a long wait for tables at lunch and dinner, this family-run establishment starting 12 years ago with only a dozen or so tables--and is now over 132. Besides pizza, the large salads, calzone, and bruschetta are delicious. Isidora Goyenechea 3141, almost corner Augusto Leguía Norte (Metro El Golf) Phone: 56 (2) 2519 4900