Travel From the Feet Up: 30 Best Destinations Paired With the 30 Best Shoes
Smart travel starts from the feet up. That's why the savviest travelers always plan their vacation wardrobe around their shoes, but just which pairs to pack depends on exactly where you're taking them. We looked to TripAdvisor's list of the Best Destinations in the World for some vacation inspiration, then paired each spot with the ideal pair of shoes: one for men and another for women. From avant-garde heels for the opera in Venice, to versatile water shoes to explore the beaches of Punta Cana, to comfy sandals for Orlando's theme parks—we’ve got your back…er, feet, covered at 30 unforgettable vacation destinations. Pack the best pair of shoes, and go!
30 Best Destinations Paired With the 30 Best Shoes
Men’s: Stylish and supportive, these statement Nike sneakers are just the thing to pound the fashion-forward (and slightly punk rock) pavement of England’s capital.
Women’s: The delicate ruffle, low heel, and rich mustard hue of these gorgeous slip-ons are an ideal way to channel the romance and whimsy of the City of Light. Wear them to sip Champagne at a moody cafe, beret completely optional.
Men’s: The Ancient Romans were never afraid of showing a little toe, so you shouldn’t be either. The contoured footbed and durable outsole of these double-band sandals ensure maximum comfort while you explore the ancient Colosseum.
Women’s: All roads lead to Rome, and you can walk them easily in Gabor Gabor’s gladiator-inspired platform cushioned sandals. Subtle silver accents take fashion and function to new heights.
4. New York City
Men’s: Exploring New York City calls for the freshest sneakers on the block—especially when they include a Poron® performance cushioning sockliner for all-day comfort—and a designer collaboration between Adidas and fashion powerhouse Raf Simons.
Women’s: Follow in the footsteps of NYC’s fashion (and influencer!) set with this modern metallic take on the classic Birkenstock sandal. Arch support and a comfy footbed allow for a fully fashionable day of browsing SoHo’s shops and the Upper East Side’s art museums.
5. Las Vegas
Men’s: A visit to Vegas calls for shoes that are sharp enough for the high roller high-life, but also so comfortable (read: cushioned footbed) that you can easily walk all four miles of the Las Vegas Strip—not to mention through the maze-like casinos.
Women’s: This stylish pair of knotted heeled sandals transitions easily from the desert’s day to night—perfect for exploring all that Sin City has to offer. This pair looks just as good at the roulette table as they would strutting around Fremont Street.
Men’s: Barcelona is as famous for its beaches as its food scene. Birkenstock’s lightweight slip-ons feature a contoured cushioned footbed, letting you hop from one locale to the other in optimal comfort and support.
Women’s: A day spent taking in beautiful art—the city features the Museu Picasso, Fundacio Joan Miro, as well as numerous landmarks by Antoni Gaudí—requires footwear that is easy, breathable, and a work of art itself. These unforgettable marigold espadrilles with tassels fit the bill.
Men’s: A pair of classic Converse Chucks is best way to take in one of the Orlando’s many fun-filled theme parks, from Disney to Epcot to Universal Studios. Plus, the canvas fabric means they’ll dry easily too—bring on the water rides.
Women’s: If you hadn’t heard, Teva’s are back in the fashion game. We love the original style with their quick-drying and adjustable nylon straps, for an Orlando vacation adventure. Pair them with shorts, midi skirts, or jeans—they’ll match everything in your suitcase.
Men’s: The sleek lines and open silhouette of this structured sandal make it perfect for both a Dubai desert safari and a night of music at the Madinat Theatre. One sandal, lots of looks.
Men’s: Woven huarache sandals let you channel the relaxed lifestyle that Madrid is celebrated for, while comfortably taking in the city’s stunning museums and El Retiro Park.
Women’s: These vibrant slingbacks are an easy way to make an outfit pop, perfect for wearing to a late-night tapas and sangria dinner. Plus, they’re the same bold hue as the red carnation, Spain’s national flower.
Men’s: These breathable slip-ons combine the good looks of a traditional smoking slipper and the comfort of an espadrille. They’ll have you covered for any surprises that Bangkok’s sensory overload may hold.
Women’s: If you’re planning on exploring Bangkok’s many temples (of course you are!), then shoes that slip on and off with ease are key. Bonus points for having a fun and colorful checkerboard print!
Men’s: New Balance’s Fresh Foam midsole cushioning offers optimal support—just what you need when cycling around Amsterdam’s beautiful canals, taking in the tulips.
Women’s: Featuring a washed cotton-canvas lining and custom contoured footbed, this modern take on a classic 1960s street shoe lets you walk (and bike) on the wild side with all-day comfort.
Men’s: Sightseeing in Milan—known as Italy’s fashion and shopping capital—calls for shoes that are equal parts comfy and chic. Enter: Cole Haan’s handsome wingtip oxfords.
Women’s: A chic pair of two-tone slingblack flats are perfect for strolling down the cobblestone streets of Milan’s Brera District—interspersed with multiple cappuccino breaks, of course.
Men’s: Cancun calls for beach shoes, and Nike comes through with an open design and water-resistant construction. These sandals are ready for sun, sand, and surf.
Women’s: These metallic sandals can be dressed up or down to suit your look: perfect for a candle-lit dinner on the beach or shopping at La Isla Shopping Village. Bonus: the jute bottom detail will look cute with any embroidered Mexican dresses or blouses you pick up.
Men’s: A good vibram sole (for optimal traction and performance) is key when spending the day discovering Prague’s sights such as Old Town Square or walking the Charles Bridge.
Women’s: Exploring Prague’s Old World charm (read: cobblestone streets) calls for increased stability and all-day heel and arch support, like you’ll find in these lightweight trekking boots.
Men’s: Streetwear rules in the creative and hip city of Berlin. Dress like a local by donning a pair of edgy, two-tone combat boots. Yes, we’re talking year-round.
Women’s: The low heel and contemporary vibe of these modern Chelsea boots mean you can tour Berlin in comfort and style, from mornings spent photographing street art to late late nights dancing in clubs.
Men’s: Given the abundance of good (man-made) beach to explore in Singapore, a sturdy pair of flip-flops is a must. The soft toe post prevents that between-the-toe blister that can ruin an otherwise perfect beach day.
Women’s: You can wear your prettiest sandals without fear in Singapore: the city-state is known for its well-kept pavements and footpath. This gorgeous pair with a flower-filled lucite heel is a must from brunch through after-dinner drinks.
Men’s: Skip the running shoes on a Budapest trip—locals say that’s a sure sign of a tourist. A good pair of boots, like these Red Wings, will provide the same comfort and fit of a sneaker, but with a slightly more polished look.
Women’s: Featuring mesmerizing historic sites and endless cobbled streets in which to get lost, Budapest is one city where you’ll want to leave your heels at home. Instead, opt for a menswear-inspired brogue that’s as comfy as it is stylish.
Men’s: The hilly coastal city of Lisbon calls for serious shoes, like Columbia’s Bahama boots, with maximum traction and optimal fit—perfect for taking in such sights as Sao Jorge Castle and Jeronimos Monastery.
Women’s: In between sightseeing, you’ll want to stop for a delicious pasteis de nata (otherwise known as Portuguese custard tarts). These chic Everlane mules were meant for afternoon cafe photo-ops.
19. Punta Cana
Men’s: Given the amount of water-friendly activities in Punta Cana, you’re going to want shoes that can keep up with you and your busy schedule. These slip-on shoes were designed for water and land.
Women’s: You’d never guess, but these stylish rose gold sandals are water-friendly. The durable construction means you can hit the beach, waves, and all-inclusive resort bar in style—without a shoe change.
20. Hong Kong
Men’s: At many Hong Kong restaurants and hotels, a “smart casual” dress code is enforced—check both off your list with these supple suede oxfords.
Women’s: Not only do these supportive flats look great, they also ensure you’re able to navigate Hong Kong’s (often) sloping sidewalks and sometimes bumpy ferry rides with ease.
Men’s: Istanbul is all about walking to take in the architecture, markets, and minarets of St. Sophia, so we recommend choosing sneakers that maximize comfort and fit.
Women’s: If you’re planning on visiting the Blue Mosque, (of course you are) you’ll be asked to remove your shoes. Be prepared with a pair of effortless and cheekily fun slip-on espadrilles.
Men’s: In Florence, you want to focus on filling your stomach with pasta and your soul with artistic masterpieces. You do not want to be focused on uncomfortable feet, so pick up a walkable pair of breathable trainers.
Women’s: These slides are so cute and comfy that the only problem on your mind will be the best angle for your selfie with Michelangelo’s David. And maybe, whether to order a carafe or a full bottle of wine at dinner.
23. Los Angeles
Men’s: Tap into Los Angeles’s famously relaxed vibe with these no-slip, “Don’t Trip” sandals. Extra comfort points for a soft, padded lining that won’t chafe. Extra, extra points for shoe selfies on the Hollywood Walk of Fame.
Women’s: The warm hue of these gold sandals channel all things summer and fun—perfect for “the golden state.”
Men’s: Pay tribute to the city of canals with some comfortable boat shoes—great for walking around the city’s back lanes or enjoying a relaxing gondola ride.
Women’s: Operatic nights at the Teatro La Fenice are a popular Venice evening activity. Dress accordingly with a pair of statement-making lemon-yellow heels.
25. Playa del Carmen
Men’s: We love how these striped espadrilles speak to the laid-back vibe of coastal Playa del Carmen. These would look great on a leisurely stroll down Quinta Avenida for tequila and souvenir shopping, too.
Women’s: Lazy afternoons spent by the resort’s pool call for cute sandals that can transition easily from daytime chill to nighttime bold at Coco Bongo nightclub.
26. New Orleans
Men’s: Whether you’re in the Big Easy for Mardi Gras or just a vacation, exploring all of New Orlean’s historic neighborhoods require shoes that are supportive and have just the right amount of metallic flare.
Women’s: New Orleans is the type of city where you don’t have to play it safe when it comes to fashion choices. The bolder, the better! These rainbow wedges will turn heads on Bourbon Street—and, thanks to the ankle strap, keep your feet supported.
27. San Francisco
Men’s: These aptly named Disruptor sneakers are perfect for tackling San Francisco’s steep streets and norm-core dress code.
Women’s: Cute and comfy is the only way to explore iconic San Francisco neighborhoods such as Chinatown, Fisherman’s Wharf, Russian Hill, and the Embarcadero.
Men’s: These understated high-tops are a great way to take advantage of Vienna’s 150-plus miles of bicycle paths. Added bonus? They look very cool for nightlife.
Women’s: For days when you don’t feel like cycling, a mix of walking and public transportation is the way to get around. These double-buckled slides have you covered for both.
Men’s: Hiking boots are the thing to explore the beauty of the Pentlands, a range of hills that stretch from Edinburgh to the small village of Carlops. Best of all? They’re waterproof, perfect to contend with Scotland’s rainy weather.
Women’s: These stylish slip-ons will keep you cushioned and comfortable as you visit such must-see sights as Edinburgh Castle (home to the crown jewels) and the medieval Old Town.
Men’s: The Ortholite® insole and padded collar of these shoes ensure your feet stay comfy as you wander around the Majorelle Garden, Bahia Palace, and Koutoubia Mosque.
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