5 Fairytale Cities In North America That Feel Like Europe

Dreaming of storybook towns paved with cobblestones, leafy squares bordered by decades-old, storied cafes, and, why not a fairytale castle on a hill?

Chances are, you’re probably looking at tickets to fly out to Europe again. After all, that’s what the Old Continent’s known for, and there’s nowhere else in the world you could find those, right? Well… have you checked in your own side of the pond?

It turns out you don’t need to fly 8 to 11 hours to experience some of that historical charm, as there are 5 North American cities that look exactly like Europe, as they were built by Europeans, after all—and rest assured, they’re just as stunning as the ‘real deal’:

Quebec City

The textbook example of a North American city that could easily belong somewhere in castle-dotted Europe, Quebec City is a French-colonial gem with cobble-paved alleys, medieval-inspired squares surrounded by cozy cafes, and a monumental château to top it off.

The most prominent feature in the city’s timeless skyline, Château Frontenac is in fact a luxury hotel opened back in 1893, and it’s heavily inspired by Renaissance castles—to the History buffs out there, it also hosted an important meeting between Churchill and Roosevelt during WWII.

Other must-sees around the ‘Old Quebec’ include the city walls, a rare example of a colonial fortification that has not been completely dismantled, and the romantic, lamp-lit Rue du Petit-Champlain, a street lined with artisan shops and boulangeries serving fresh-out-the-oven butter croissants and pastries.

Valladolid

A postcard-ready Spanish-era town tucked away in the Yucatanese heartland of Mexico, miles away from the tourist-packed coast, Valladolid is everything you’d hope a 16th-century townscape to be… and then some.

At the town square, you’ll find an imposing Cathedral of San Gervasio, built in ocher stone with an ornate Baroque facade. Not far from the church, there’s an equally impressive Convent/Temple of San Bernardino de Siena, established all the way back in 1552 by the Franciscan Order.

If you’re looking to see something truly unique, however, make sure you stroll up Calzada de los Frailes, a historic cobblestone thoroughfare flanked by colorful houses that are centuries old. On that note, don’t miss Casa de los Venados, the best-preserved colonial mansion in historic Valladolid.

San Juan, Puerto Rico

Who said you need to grab a passport and fly abroad to experience some of that European-esque Old World charm? A short 3 to 4-hour flight from most East Coast hubs will take you straight to San Juan, the lively capital of Puerto Rico:

Settled by Spanish colonizers during the Age of Discoveries, it retains much of its traditional Iberian character, including the warm-tone house facades, the stone-covered streets that lead to secret plazas, and even coastal walls that formerly protected the colony from pirate invasions.

Guarding the entrance of San Juan Bay, there is a 16th-century San Felipe del Morro Castle, while the Santa Catalina Palace is the oldest governor’s mansion still in use in the Americas, and San Juan Bautista Cathedral was raised as early as 1521. Yep, this makes it one of the oldest on this side of the pond.

Charleston, SC

Now, we get it if you don’t fly overseas for European aesthetics and beautiful architecture. In that case, there’s always the much-overlooked, yet undoubtedly alluring Charleston, in South Carolina: founded in 1670, it is one of the oldest continuously inhabited cities in America.

Picture an 18th-century church, St. Michael’s, attended by none other than George Washington, the Old Exchange, built by the British as a customs house, and the Rainbow Bow, a string of pastel-hue townhouses that immediately evoke a back street in London’s Notting Hill.

For the History buffs out there, you should probably know that the 1772 Heyward-Washington House is among the best-known examples of Georgian-era houses in Charleston. Lucky for us, it’s now open as a museum, entirely furnished with period pieces.

Lunenburg, Nova Scotia

We’re going back north of the border for this one. We’re sure you’d heard of Quebec City already, but how about Lunenburg, the most precious gem in the Nova Scotia crown? We mean… you don’t find near-intact colonial settlements that remain almost exactly as the British left them.

Old Town Lunenberg and its brightly-painted harborside house facades are a UNESCO World Heritage Site, in recognition of their enviable state of preservation and preserved heritage, and there’s no better way to see it in full than, you know, walking around at random.

That being said, St John’s Anglican Church is a good place to start, with its Gothic Revival portal and starry-night ceiling; or maybe you’d rather check out the Knaut-Rhuland House, built by one of the city’s founding fathers—and if we may add, coffee lovers’ paradise No. 9 Coffee Bar is a short 2-min. walk.