The 2020 Legend Awards are meant to serve as inspiration for future travel—when it is safe to do so. Learn more about this year's awards on our methodology page.
Between the 13 Departures' editors who weighed in on their favorite cities, we have traveled to all seven continents over the last 12 months. And with each trip, whether visiting an entirely unfamiliar city or the city we grew up in, we’ve challenged ourselves to immerse in the local culture. That means trying the new restaurants, learning the phrases the locals use, and poking around the it-neighborhoods. It means saying “yes” if the privilege of participating in a cultural event arises. And twist our arms if it doesn’t mean drinking like the locals, whether that calls for sampling the wines made just outside the city or the whiskey distilled in the heart of town.
And though we of course fight to remain objective, playing favorites is an inevitability of travel; There will always be cities that certain travel palettes gravitate toward. And among the editors who shared their favorite spots, we have foodies, art and architecture aficionados, outdoor sports enthusiasts, fashionistas, and history buffs, all of whom are drawn to different destinations.
The 2020 Legend Awards honorees for our editors’ favorite cities represent the global hubs that most excited us in the last year. From the hidden corners of Paris to the jazzed-up streets of New Orleans, these are the Departures editors’ favorite cities around the world.
Cork, Ireland
“Cork is a city that has so far really flown under the radar. With great live music, a boisterous pub culture, and a food scene to rival some of the best around the world, Cork is a destination worth seeking out. Plus, the city is only a short 15-minute drive from Blarney Castle, so you can mix a bit of the old with some of the new happenings going on around town. Head to the Victorian Quarter for great shopping, bars, and restaurants, or wander over to the Huguenot Quarter for quaint coffee shops and the Cork Opera House and Crawford Art Gallery. For an unforgettable dinner, check out Ichigo Ichie—it’s the only Michelin-starred restaurant in the city—or for something more traditional, visit Gallagher's Gastro Pub.” — Sean Flynn, Deputy Digital Editor
San Miguel de Allende, Mexico
“San Miguel is like the perfect fairytale escape: You’re surrounded by beautiful colors and architecture; there are cute shops, stunning art galleries, and yummy restaurants around every turn; and everyone there seems to be in vacation mode. My visit there was the most relaxed I have ever been in my entire life—no other city can top it.” — Erin Agostinelli, Editorial Operations Manager
Milan, Italy
"Milan used to be thought of as not much more than a dour industry hub, concealing its charms behind marble facades and the chic primness of its citizens. But in recent years, the city has begun making the wealth of its design, fashion, and culinary output much more accessible to travelers. Now it’s a cultural powerhouse filled with cutting edge art and architecture to complement its other more historical attractions. And it’s still every bit as chic as it always was." — Jeffries Blackerby, Departures Editor In Chief
Pattaya City, Thailand
“It’s filled with incredible local cuisine and food markets, shopping, and stunning beaches while being more off-the-beaten-path if you’re looking to experience Thailand without taking a trip to its capital. With the city’s eastern Gulf coast location, you can charter a boat and be relaxing on one of the smaller islands in minutes.” — Alessandra Amodio, Digital Photo Editor
Alexandria, Virginia
“Despite being biased towards Virginia (I was born and raised in Vienna), Alexandria is not only a stone’s throw to Washington, D.C., but is rich in history in its own right. Nestled along the Potomac River, Alexandria hasn’t lost its charming 18th- and 19th- century architecture. It really does feel like you’ve been transported back in time to a quaint Scottish town. Speaking of, the town itself holds a strong Scottish heritage and visitors can enjoy the Scottish Christmas Walk Weekend, usually held the first weekend in December. Alexandria is also bustling with luxury boutiques, art galleries, and chef-driven restaurants. Some of the best spots in Alexandria have historic significance (King Street in Old Town Alexandria and George Washington’s hometown), others have fictional splendor (there are places tied to Lord of the Rings, Harry Potter, and Pirates of the Caribbean). Most notable though, is the Torpedo Factory Art Center—the nation’s largest grouping of working artists in one place—where visitors can peruse fine art to ceramics, purchase from one of the studios or gift shops, or visit several galleries within.” — Deanne Kaczerski, Executive Digital Editor
Edinburgh, Scotland
“Every time I’m in Edinburgh, I fall in love with the city all over again. Maybe it’s the history and the big castle that looms over the city, or the friendly people, or the atmosphere of academia—I just consider moving there each time I leave. My favorite thing to do? Stay a night at The Balmoral Hotel (and eat at the raw bar!), have breakfast at Dishoom, and make time to wander the streets of the West End, where cute boutiques and even cuter pubs abound.” — Ellie Nan Storck, Associate Digital Editor
Charleston, South Carolina
"There are very few places in the world that embrace you, as a traveler, as an outsider, like Charleston. Stay at a hotel like the Dewberry, housed in a gorgeous, mid-century Federal building, and the head bartender will spend an hour talking to you about his favorite city spots. Walk into a shop like Croghan’s Jewel Box, a darling gem of a store selling silver and estate pieces on King Street, and the family who owns the business will great you like a long lost relative. And eat bone-marrow infused bread pudding over brunch at the MacIntosh, helmed by a wunderkind young chef, Ayanna John Carter, and you can see heart and youthful promise in the city’s ever-changing culinary scene." — Jacqui Gifford, Travel + Leisure Editor In Chief
Cape Town, South Africa
“Cape Town may be the most beautiful city in all of Africa, with its breathtaking Table Mountain, revitalized Victoria & Alfred Waterfront, and oft-Instagrammed Bo Kaap district. But it’s more than a collection of beautiful landmarks. What makes this South African gem sparkle most is its people: the artists leading the contemporary scene at the Zeitz Museum of Contemporary Art Africa, the chefs cooking up innovation at Michelin-starred restaurants like The Test Kitchen and Aubergine, and the tastemakers who have turned once-struggling neighborhoods like Woodstock into thriving epicenters of culture and design.” — Jackie Caradonio, Travel Director
Malmö, Sweden
“Malmö has all the energy of an up-and-coming luxury destination. Just a half-hour train ride from Copenhagen, Malmö’s food scene is hyper-local (I’m partial to this lovely wine bar in Gamla Väster, Julie) and a lot of Scandinavia’s highest-end design talent is concentrated in Malmö right now. And by choosing a destination in southern Sweden, it doesn’t hurt that you’re in such close proximity to the near-perfect Swedish spas on the Baltic Sea, like the luxurious, coastal relaxation center Ystad Saltsjöbad.” — Maya Kachroo-Levine, Digital Special Projects Editor
New Orleans, Louisiana
“I have enjoyed this city with and without kids, and we can’t wait to return to keep exploring this ever-changing city. I love the cobblestone streets, music, and architecture in the French Quarter and all the restaurants to try. I don’t tire of gazing at the old homes while riding the St. Charles Streetcar line through the Garden District and then exploring the neighborhood at the end of the line. I love the art along Rue Royale and at the museum at the New Orleans City Park, where I can also take my kids to play mini-golf, paddleboat among the Spanish moss-covered trees. The Zoo and Aquarium are easy to access and worth multiple visits. I love the unique flavorful foods that are so unique to the area. I like to not need a car until we decide to take day trips to explore plantations and drive to eat on the beach in Baton Rouge.” — Devin Traineau, Travel + Leisure Associate Photo Editor
London, England
“It’s my home city, so I’m biased, but I’ve got to say London. Not only for what it’s always been, but for its now amazing and continuously evolving culinary scene; even French restaurant groups like Big Mamma are setting up shop in the city.” — Tal Dekel-Daks, Audience Engagement Editor
Paris, France
“This is hugely unoriginal but Paris, not so much for any new developments—although there are plenty of cool new restaurants, bars, and hotels—as for what it has always been: an epicenter of culture and sophistication. I love it not despite its snootiness but because of it. I love how little it fundamentally changes.” — Julian Sancton, Senior Features Editor
New York City, New York
“It goes without saying that the Big Apple is one of our favorite cities. It’s home to some of the world’s best restaurants and hotels, top entertainment and fashion, and, of course, more Instagram-worthy attractions than almost anywhere else. But what we love most about New York is that there’s a version of it for everyone, whether you’re a foodie or a history buff, a museum geek or a culture vulture, a die-hard fashionista or a Broadway fanatic. Whatever makes you tick, this city’s got plenty to keep you coming back for more.” — Jackie Caradonio, Travel Director
Sydney, Australia
"For sheer beauty, it’s hard to beat Sydney, a city wrapped in miles of coastline and blessed with more great beaches than you could visit in a week. But there’s much more than meets the eye here – there’s a lot for the discerning palate as well. Sydney’s restaurant scene is among the best in the world, with talented chefs turning out Italian, Greek, Lebanese, New Australian, traditional English, and a seemingly infinite variety of Asian cuisines—as good if not better than what you’d find in their home countries." — Jeffries Blackerby, Departures Editor In Chief
Nantucket, Massachusetts
“I’ve been going since I was a child, so there’s definitely some nostalgic value there, but I’ve grown to appreciate its charm even more as an adult. It’s so well-preserved (cobblestone streets, no traffic lights or neon signs, buildings below 40 feet, and certainly no fast-food chains) and feels like you’ve been transported to a whaling town just as it was in the 18th century.” — Annie Davidson, Associate Editor
Bangkok, Thailand
"Put simply, Bangkok is teeming with life. Also: color, flavor, aromas, and so much energy. One could spend hours meandering along the stunning Chao Phraya River, exploring narrow streets, stopping for delicious food in the bustling markets (think fresh mango sticky rice or red curry), visiting iconic temples, and discovering all the local treasures held in this exciting, cosmopolitan city." — Ellie Nan Storck, Associate Digital Editor
Los Angeles, California
“Watching LA change over the last 10 years has been a treat for travelers flocking to Southern California. The food scene in LA finally stopped trying to one-up New York City in favor of just doing their own thing. The result? Renowned chefs swarmed to LA to revel in Mexican and pan-Asian flavors and the ever-enviable ‘California fare’ that was put on the map by the likes of Gjusta in Venice Beach and Sqirl in Silverlake. The hospitality scene in both DTLA and Santa Monica is on the rise, for good reason—it’s hard to resist either neighborhood.” — Maya Kachroo-Levine, Digital Special Projects Editor
Austin, Texas
“Before Austin was a big city, it was a charming little university town. And even though it’s now one of the fastest-growing metropolises in America, it still retains the close community vibe that locals love (and won’t hesitate to tell you about any chance they get). You can’t go wrong when it comes to the food—you haven’t lived until you’ve had queso at every meal—and you’d be hard-pressed to find a better live music scene anywhere on the planet. Even as big-name chefs, hoteliers, and billion-dollar tech companies arrive, there’s something comforting about Austin that makes everyone, no matter who they are or where they come from, feel like they’re at home.” — Jackie Caradonio, Travel Director
