Picture yourself on the last night of your next trip to Italy. 

You walk to the Cathedral of a small town you now know by heart with new friends at your side.  You’re looking forward to one last dinner, sharing laughs over wine, expressing yourself, and ordering food in Italian.


Every meal has been an adventure in taste and companionship. You’ve discovered the quiet corners of this small town, lingered in the market, sipped cappuccino at the local cafè. 

You’ve done so much more than just “get by” in Italian. You opened up and became comfortable expressing yourself- something you’ve never done before. You’ve chatted with locals and feel connected to the language and culture.  And you’ll take that with you for the rest of your life.

Sounds beautiful, doesn’t it? And yet, if you’re like many people I talk to, this dream may sound more or less impossible.


Maybe you’ve even planned a trip to Italy before, left yourself extra time to go deep and experience the culture, only to go home with the nagging feeling that you missed something essential. 

Maybe you’ve got a deep, visceral connection to Italy, and you’re just never going to be satisfied with the postcard version. 


What you really want is to make some small corner of Italy feel like “home.”


If that sounds like you, then read on. 

In this post, you’ll learn to make your next trip to Italy authentic and unforgettable. One where you’ll come away feeling connected and transformed.  Like you’ve left a small part of yourself in Italy–and will no doubt, return someday.

In today’s post, I’ll share some of my favorite ways to find just the right destination to slow down, soak in the culture, and truly experience Italy.  I’ll teach you how to wander the sidestreets of authentic, beautiful (and too often overlooked) cities or towns. 


I’ll also share a few secrets I’ve learned organizing five language retreats over the years so that you’re much more likely to experience life like the locals do–and maybe even end up chatting with them as well. 


Take a moment today and learn some new ideas for experiencing Italy so that your next trip feels like coming home.


Start by sidestepping the tourist hustle and discover Italy’s hidden gems.


When it comes to choosing the right destination, sometimes the difference between perfect and disappointing is just a 30-minute train ride.


So get on that train and watch the city buildings give way to vineyards, fields of sunflowers and pastures.  Before you know it, you’ll find yourself passing smaller, lesser-known towns that are still packed with history, beautiful landscapes, sights, and, most of all, experiences.

For example, don’t make Milan your final destination. It can be too much, too fashion-oriented, too crowded, too expensive, too touristic. 


Hop on the train for 45 minutes and come to Cremona, where I live. Visit a breathtakingly beautiful town, totally off the tourist track. Lose yourself in the side streets, wander past shy locals in an unassuming community. 

The same goes if you’re planning to arrive in Rome, Florence, or Venice. Push on and leave the stress-inducing lines and crowds behind. You’ll be so glad you did.


You’ll experience an entirely different Italy in those smaller towns with their strong identities and friendly communities. You’ll still discover beautiful piazzas and Renaissance buildings.  You’ll wander over cobblestones and let the conversations between locals wash over you.


Italy is so ridiculously crowded with beauty that it’s impossible to go wrong. 


Once you arrive, stop and pay attention to the way locals spend their time.


Over the years, I’ve learned to plan my retreats based on the ‘clock of the town.’ And I even organize people-watching activities. 


If you want to try this on your own, just pick a comfortable and inspiring place like a market, piazza, or un bar cafè and open your eyes, ears, and heart.

Slowing down and truly seeing how people live in small-town Italy takes some time and observation.  But you can start by noticing when locals are taking walks, having aperitivo, doing the shopping, taking their passeggiate with their famiglia e amici. 


Italians put importance on their open-air social lives, and I think it’s so important to be a part of it and take time to blend in with it while noticing. You’ll start to feel more like a local without even speaking–and definitely without walking around in a herd of tourists or with your nose stuck in a guidebook.


Once you get the hang of it, you can start doing things like locals do.


Shop and dress like an Italian–if you like.


If you’ve ever asked yourself whether you look too much like an outsider or tourist and wondered how you could look more like a local, you’re not alone. But my advice to you is this: the best way to decide what to wear is to make observations on your own. 


Italians, actually do this as second nature; they notice every detail about what other people wear and in their appearance. So, by paying attention to how the people around you dress, you’ll already be taking part in an authentic activity.


Whenever I organize a retreat, I encourage learners at the clothes market to notice how Italians buy clothes. Often, they’ll wander between open-air stands, checking quality textiles, sewing, and brand names. 


You certainly don’t have to change your entire wardrobe to fit in, but learning to dress like a local can be a lot of fun.


Of course, if you want a truly authentic experience, eat like a local, too.


I cannot emphasize the importance of taking the time to actually shop for your own food. 


Visit an outdoor market or stop by an alimentari.


Alimentari are so much more than grocery shops. They’re THE place where people go when they want quality food. 


Like with all things concerning food, Italians bond over the right kind of bread and the best affettati. In a small town, the owner and the locals will be curious about you. So stop in and grab a picnic or snack a few times, and you’re likely to find yourself in conversation as well. 


You’ll also want to discover the local Italian restaurants. 


If you’re looking for a restaurant experience you won’t regret, here are a few things to avoid. (Assuming you want to skip tourist traps).


Look for restaurants with NO photographs on menus or outside the restaurant. NONE. The menu shouldn’t be in English. Maybe you’ll see a translation of the dishes below, but if there isn’t, it’s even better because it means that only locals go there, and nobody will give you the tourist treatment. 


There shouldn’t be tourist dishes on the menu like “ fettuccine Alfredo” (not an Italian Dish). 


And the menu should not be too long. A good menu should be simple and not offer too wide a selection of dishes. 


Restaurants that offer less have made a choice to focus on quality. 


You can also check to see if the ingredients are local. And look for family-run restaurants or trattorias, which are also usually a safe bet.


Don’t forget to delve into Italian Coffee Culture.


Going regularly to a cafè is an incredible way to get to know a place. People share all sorts of stories over coffee, discuss plans for the day, the news, soccer,  the weather, how life was so much better before, and what fun events might be scheduled for the evening. 


After settling in Cremona, I started stopping regularly at my local cafè. Day after day, I’d have my cup of caffè macchiato or cappuccino (if it’s winter) at the same time. 


Even if you’re just planning to stay for a couple of weeks, making a habit out of stopping in the same cafè can help you feel just a bit more like a local–just a bit more at home in Italy.


Visit the right places, keep a slow pace–and you’ll meet locals.


When you pick the right place to visit, meeting locals and starting conversations often happens naturally. 


In my hometown, Cremona, for example, you’ll find that people tend to be warm and welcoming. If you’re from an Anglophone city, you might be surprised at the way Italians in small towns will stop and strike up conversations with passersby. But here, in Italy, this is just part of daily life–especially in small towns off the beaten path. 


When I take groups out for an afternoon of observation and art, if a local sees us painting a landscape, they might pass by and say, “Anch’io dipingevo una volta ma poi ho smesso! Che bello quello che fate!”  And the conversation just flows from there. 


Because you’ve chosen to visit a small town, you WILL meet those people again and ecco! You’ve created a connection.  Which brings me to my last point…


Don’t forget to learn some Italian before you go.


And no, you don’t have to wait until you’re fluent in Italian to come to Italy and start to fall in love with a special small town or city. In fact, sometimes, that feeling of being absolutely part of a place, culture, and community can be what inspires you to finally express yourself in Italian.


Still, learning at least a little Italian before you leave can help you be ready to take that train past the beaten track and beyond the tourist destinations. It can help you navigate the small family restaurants and trips to the alimentari.  


Learn to ask, “Mi potrebbe consigliare una specialità tipica ?” “Could you recommend a dish from around here?”  And you’ll find you get suggestions for local dishes AND initiate conversations because food is THE greatest icebreaker in Italy.  


Whatever phrases you come to Italy with will help you feel more a part of things. 


It can be as simple as learning what to say when you don’t understand: 


Scusi, potrebbe ripetere? Non sono sicura/o d’ aver capito.  Could you please repeat that? I’m not sure I understood. 

This is the kind of expression that helps you stall and not panic when someone speaks to you and you don’t understand. When you say this, people understand that all they have to do is slow down a bit. 


And you let yourself off the hook for having to understand absolutely everything before you can start feeling at home in Italy.


Are you dreaming of your next trip to Italy? Tell me all about it.


Stop for a minute in your busy day and imagine you’ve just run into me in a cafè in a perfectly small Italian town. What does your stay in Italy look like or feel like? How do you interact with the locals? What experiences do you absolutely want to have while you’re here? How do you want to feel? 


And more importantly, who do you want to be after your next stay in Italy?

Tell me all about it in the comments. Or get in touch. Is this is an experience that you’d like to be a part of, join the waiting list to be a part of my future retreats here.

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