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We all have that friend who won’t shut up about their semester abroad in Milan. The aperitivo culture! The architecture! The vibe! But here’s the thing: you don’t actually need to drop $1,200 on a transatlantic flight to get your European fix.
From coast to coast, North America is hiding some seriously charming cities that’ll make you feel like you’ve stepped off a plane in Italy (or at least somewhere decidedly more European than your current zip code). Whether you’re chasing cobblestones, carbs, or just that ineffable European elegance, these spots deliver.
Let’s dive in.
1. Boston Massachusetts
If you want to feel Italian without leaving the country, Boston’s North End is your best bet. This is the oldest Italian neighborhood in the US, and unlike some “Little Italys” that are more like tourist traps, the North End is still genuinely Italian.
What to Do: Start your day at Caffè Vittoria, the oldest Italian café in Boston (since 1929), where the espresso is strong and the old-world charm is stronger. Wander the narrow, winding streets—yes, they’re actually cobblestone—and pop into Mike’s Pastry or Modern Pastry for cannoli. (Locals have strong opinions about which is better. The correct answer is: eat at both and decide for yourself.)
For lunch, grab a slice at Galleria Umberto (cash only, closes when they sell out, zero frills, completely perfect). Dinner? Giacomo’s if you don’t mind waiting in line, or Neptune Oyster if you want some of the best Italian seafood outside of, well, Italy.
And if you’re there in summer, the Feast of Saint Anthony and other Italian festivals basically turn the North End into a street party that would make any Italian nonna proud.
Book Your Trip
| Buses to Boston | From $3 | |
| Trains to Boston | From $6 |
2. Montreal, Quebec
Montreal is what happens when French elegance and North American energy have a baby, and that baby grows up to be impossibly chic. While it’s more Parisian than Milanese, the European vibes here are strong, and the Italian influence is still very present.
What to Do: Start in Old Montreal (Vieux-Montréal), where the cobblestone streets and 17th-century architecture will have you doing double-takes at your map to confirm you’re still in Canada. Embrace the leisurely European culture and enjoy breakfast at a sidewalk café..
Head to Little Italy (La Petite-Italie) for lunch at Marché Jean-Talon, one of North America’s best public markets. Grab some fresh pasta, aged parmesan, and maybe a porchetta sandwich. The neighborhood genuinely feels like an Italian village transplanted to North America.
Spend your afternoon wandering Le Plateau or Mile End—both neighborhoods have that effortlessly cool, European residential vibe. Stop at St-Viateur Bagel or Fairmount Bagel (another fierce local rivalry) because Montreal bagels are a thing, and they’re spectacular.
For dinner, make a reservation at Nora Gray or Le Fantôme. Both do Italian-inspired cuisine so well you’ll question why you’d ever need to go to Italy. End your night with drinks on a terrace (Montrealers are obsessed with their terraces) and practice your French. Or your Italian. Or just stick with English—everyone speaks everything here.
Book Your Trip
| Buses to Montreal | From $10 | |
| Trains to Montreal | From $14 |
3. San Francisco, California
San Francisco’s North Beach is where Italian immigrants, Beat Generation poets, and sourdough bread all collided to create one of America’s most charming neighborhoods. It’s got that hilly, European city feel (hello, San Francisco topography) mixed with old-school Italian-American culture.
What to Do: Start with coffee and a pastry at Mama’s on Washington Square. Yes, there will be a line, no, you don’t care because you’re on vacation. Walk off breakfast by climbing the Filbert Steps for stunning views and the feeling that you’re definitely in some Mediterranean hillside town and not California.
Pop into City Lights Bookstore, the legendary independent bookshop that published Allen Ginsberg’s “Howl.” Then head to Washington Square Park to people-watch and soak in the neighborhood energy.
Lunch at Tony’s Pizza Napoletana (the owner literally won the World Pizza Cup in Naples) or Liguria Bakery for focaccia that’ll ruin all other focaccia for you. Spend the afternoon gallery-hopping or checking out Coit Tower and its Depression-era murals.
For dinner, go full Italian-American at Original Joe’s. End your night with a nightcap at Vesuvio Cafe (another Beat Generation haunt) or Tosca Cafe, where the atmosphere is so old-school San Francisco it hurts.
Book Your Trip
| Buses to San Francisco | From $9 | |
| Trains to San Francisco | From $32 |
4. Leavenworth, Washington
Ok so, Leavenworth is Bavarian, not Italian. But this place commits so hard to its European theme that it deserves a spot. In the 1960s, this dying logging town decided to reinvent itself as a Bavarian village, and honestly? It worked.
What to Do: The whole town looks like someone copy-pasted a chunk of the Alps into Washington State. Every building has Bavarian-style architecture, from the Starbucks to the Safeway. It’s kitschy, yes, but also kind of magical.
In winter, the town goes ALL OUT for Christmas with the Leavenworth Christmas Lighting Festival: half a million lights, carolers, the works. Summer? Go hiking in the nearby Alpine Lakes Wilderness, then cool off with a beer at Icicle Brewing Company.
Year-round, stuff your face with schnitzel and sausages at München Haus, and yes, there are approximately 47 places to buy cuckoo clocks. Embrace it. You’re in fake Bavaria.
Book Your Trip
| Buses to Leavenworth | From $21 | |
| Trains to Leavenworth | From $10 |
5. Chicago, Illinois
Chicago doesn’t get enough credit for its Italian-American heritage, but the city has multiple vibrant Italian neighborhoods and that certain European-city energy—grand boulevards, world-class architecture, and a food scene that takes itself seriously.
What to Do: Start in Little Italy on Taylor Street. Grab breakfast at Fontano’s Subs or Pompei, then walk it off exploring the neighborhood. Hit Mario’s Italian Lemonade if it’s warm out—this seasonal spot has been serving Italian ice since 1954.
Eataly Chicago is like a shrine to Italian food and culture, with multiple restaurants, a market, cooking classes, and more mozzarella than you knew existed. Spend an embarrassing amount of money on imported pasta and olive oil. No regrets.
For a fancy dinner, Piccolo Sogno has a stunning patio that genuinely feels like you’re dining in Italy. Or go old-school at The Rosebud or Club Lucky for red-sauce Italian-American classics.
Book Your Trip
| Buses to Chicago | From $8 | |
| Trains to Chicago | From $6 |
6. Philadelphia, Pennsylvania
South Philly’s Italian Market is the oldest and largest working outdoor market in America, and it has a realness that some more polished “Little Italys” have lost.
What to Do: 9th Street is where it’s at. Start at Claudio’s for cheese and deli items, then hit Fante’s Kitchen Shop (around since 1906) for every Italian cooking implement imaginable. DiBruno Bros. is cheese heaven, so don’t be afraid to sample everything.
Lunch at Paesano’s for what many call the best sandwich in Philly (bold claim in this town), or grab a roast pork sandwich at DiNic’s in Reading Terminal Market (slightly outside the Italian Market, but unmissable).
Walk through the neighborhood and you’ll see Italian flags hanging from row houses, old-school social clubs, and grandmothers who’ve lived there for 60 years. It’s not polished or touristy; it’s real.
For dinner, Scannicchio’s or Monsu both do elevated Italian in intimate settings. Or go full red-sauce at Ralph’s Italian Restaurant (since 1900, family-owned, cash only).
Book Your Trip
| Buses to Philadelphia | From $5 | |
| Trains to Philadelphia | From $6 |
7. Solvang, California
Okay, Solvang is Danish, not Italian. But if we’re talking European escapes in unexpected places, this Central California town delivers. Founded by Danish immigrants in 1911, it’s committed to the theme in a way that’s either delightful or deeply weird, depending on your mood.
What to Do: The entire downtown looks like a Hans Christian Andersen fever dream, with windmills, half-timbered houses, bakeries selling æbleskiver (Danish pancake balls) on every corner. Olsen’s Danish Village Bakery and Mortensen’s Danish Bakery are both excellent for pastries and carb-loading.
Wine tasting! Solvang is in the Santa Ynez Valley, aka wine country. Hit Demetria Estate, Buttonwood Farm, or any of the dozens of tasting rooms downtown. Many have that European villa aesthetic.
Wander the shops (lots of Christmas stores and imported Danish goods), check out Mission Santa Inés for some California history, or rent bikes and cruise around town.
Stay at Hotel Corque or one of the many Danish-themed inns. Have dinner at Hadsten House or Root 246 for farm-to-table California cuisine, or go full smorgasbord at Solvang Restaurant.
Book Your Trip
| Buses to Solvang | From $3 | |
| Trains to Solvang | From $4 |
Will any of these cities make you forget about Milan? Probably not—Milan has centuries of art, fashion, and history that no North American city can replicate. But can they give you cobblestones, incredible Italian food, and that feeling of being somewhere special without the jet lag? Absolutely.
So grab your passport (well, for Montreal), pack your stretchy pants, and go find your European fix without leaving the continent. Your semester-abroad friend can keep their stories. You’ve got cannoli to eat.
