My Top Three Unplanned Italian Destinations

When it comes to Italy, it is easy to ramble on about the impeccable cuisine, high quality coffee, beautiful language, the winding canals of Venice, breathtaking coast of Cinque Terre and the ancient cobblestones in Rome.

From top to bottom, it is arguably my favorite country. It is also one of the first places I recommend to anyone who is planning a trip to Europe.

There are so many obvious reasons to love the country. Sure public transportation comes whenever it feels like it, and there is hardly any good WIFI. But there is no doubt Italians set the standard for espresso beans and easy afternoons.

After considering all of the cities I visited, I decided to focus on the lesser known places I ended up.

There is countless amounts of travel literature out there that will fork out a 14 day itinerary for anyone. If you want to make sure there isn’t a church left unseen or a statue left un-photographed.

The cities in this list weren’t planned and never popped up when I started compiling information. But the most important travel advice I can give while traveling is don’t be afraid to find your own adventure. Also, feel free to use my particular road map as a guide.


My first trip to Italy a few years ago, I found myself in a tiny village between Rome and Naples. I was circling tiny cobblestone streets 2 o’clock in the morning and making our way between the only two bars within walking distance.

Itri is not so much a destination recommendation as a suggestion to spend some time away. Get away from big towns and cities, in a real Italian village and see how real Italians live. I owe my stay in this particular village to a good friend who was visiting family and was gracious enough to take me along.

Village Life

I spent my nights drinking €2 glasses of Prosecco at Bar Dello Sport and took a day trip to the nearby beach town of Sperlonga. There I got to put my feet in the Mediterranean Sea for the first time. Sure when nothing opens until 3pm you might get a little restless, but if you have the time, bask in the true culture shock.

If you do find yourself itching for a big city, there’s always a Trenitalia station near by and Rome isn’t going anywhere.




We decided to use to find hosts in all the major cities we wanted to visit. I didn’t realize though, that we would start receiving invitations from nearby cities we were looking at. But that is exactly what happened a few years later on my second trip to Italy.

We accepted our first invitation from a guy in Mantua, just an hour train ride from Verona. There we found ourselves in the real life setting for one of Shakespeare’s most famous plays.

Now being the Shakespeare nerd that I am, I was pleasantly surprised (and probably way too excited) to find out that we had stumbled across Romeo’s banished city. The very place he first heard of Juliet’s death.

Juliet’s balcony was a must see for me, but we found out that this charming little town had so much more to offer than just close proximity to Verona.

We spent our first evening in Mantua having drinks by the Mezzo Lake. This was the best places to watch the sunset and then we enjoyed our first real home cooked Italian meal.

Finding Love

We also found that the cities archaeological museum houses the “Lovers of Valdaro.” For no entry fee, you can see the 6,000 year old embracing skeletons found and excavated from their grave less than 10 miles from Mantua. This is something worth seeing if you’re ever in the Northern part of Italy.

But the best and most unexpected surprise was attending my first Rugby game in the nearby city of Viadana.  Being the not-so-huge sports fan that I am, I was shocked at how much fun a small community Rugby game could be. The tradition of fans bringing home cooked food and champagne to enjoy after the game was the real reason I enjoyed it so much.

The teams celebrate if they win or lose. It’s all just about having a great time!



When it came down to wine tasting in Italy, I always had this idea that the best experience I could ever have would be somewhere in Tuscany. Not to say that I would call myself a wine expert. But the idea was there and the assumption that it doesn’t get better than wine tasting in the hillsides somewhere near Sienna, with fields of sunflowers in view. That was until I went to Bergamo.

Okay, so I have yet to actually spend time wine tasting in Tuscany with sunflowers anywhere in sight (when I went I just ate a lot of gelato and the sunflowers weren’t in season). But still.

I ended up in Bergamo the same way I ended up in every other unplanned destination throughout Europe, by a couchsurfing invitation. Depending on the profile and a little research on the city, we accepted invitations based on the idea that we wanted adventure. We wanted to see as much as we could through the eyes of a local, and this city was no different.

Why not spend some time with the guy who had hosted hundreds of travelers from around the world? I couldn’t think of reason not to either.


Wine and More Wine

This was my favorite of all the places I stumbled upon in Italy.  The highlight was (shocker) a day of wine tasting at the La Rocchetta winery near Lake Iseo.  Our gracious host offered to let us use tickets he had previously purchased for himself for a tour that was entirely in Italian. That’s right, entirely in Italian.

I didn’t understand a word of the tour. But our extremely helpful tour guide was nice enough to summarize each part briefly in English.  He also politely acknowledged the notable (yet still inferior) wines of California.

My overall experience at this particular winery was amazing. The wine was incredible and the food laid out was delicious. We spent the rest of the day by the lake enjoying full bottles of some of the best wine I had in Italy.

If that isn’t enough to make Bergamo one of my favorite pit stops, you can always take a car to the upper town. There you can enjoy an incredible city view of the town below and some more ancient Italian history. Just in case you don’t make it to Rome.


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