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Travel Tips: Choosing Where To Travel In Italy

written by M.E. Evans April 3, 2015

It’s summer and the emails are starting to come in asking for my recommendations for travel. Since I’m working on a series of guides and some super in-depth posts about travel that I’ll have up soon, I’m just going to keep this short and sweet with the highlights of my favorite places to go. I hope this helps at least some of you plan your Italy trip this year.

Choosing a destination depends on what kind of traveler you are and what you’re seeking. Are you a history buff? A food lover? Wino? Artist? Do you love culture and people-watching (legal stalking)?

I’m personally really into culture. I love watching people. If you see me in Florence I’m probably sitting on a bench taking photos of perfect strangers while they smoke cigarettes or talk about their partner or cake recipes. If this sounds like you then you might want to do an off-the-beaten-path trip. Honestly, one of the best ways to travel Italy in my opinion is to pick somewhere less touristy and spend a good amount of time there. There are tiny towns and villages throughout Italy that don’t get a lot of attention in tourism magazines but are well worth visiting if you’re looking for an authentic cultural experience.

Florence, Rome, and all of those places are beautiful, historical, and amazing but they’re swamped with visitors and because of that a lot of the charm is lost as restaurants, stores, try to accomodate visitors. I’m not entirely complaining about that because it did bring large coffee cups to Florence, God bless ya’ll, but it also removes the “authenticity,” and love that normally goes into Italian products, and food, from certain areas. Sometimes in larger cities if you want to really experience them the best way to do it is with a local, or a ton of research to avoid tourist traps which can certainly be exhausting. However, if art, history, and architecture are important to you then working larger cities into your trip is probably a good idea. I vote for going off of the beaten path and spending most of your vacation there but maybe taking short weekend trips to larger cities. For example, I love Gaiole in Chianti. Obviously, it depends on how long you have off.

Gaiole In Chianti

Gaiole In Chianti

Something that I can’t emphasize enough is renting a car if you have ten days or a couple weeks. I’m the world’s worst driver yet I managed to drive from Florence all the way to Sorrento with my friend, Jason. I didn’t kill anyone (or at least not that I know of). It was very affordable (seriously, I was a college student at the time, it was cheap), and it was such an amazing experience. It was one of the funnest things I did in school.

If you’ve got a few weeks I’d recommend starting in Milan and driving all the way to Puglia, stopping in small villages and big cities along the way. Keep in mind that Italy is smaller than a lot of states in the United States so it’s not a long drive at all to go from one end to the other. I can’t think of a better way to see the entire country, meet people, and experience Italy in all it’s glory. Just imagine all of the majestic chest hair that one could see while exploring the entirety of “The Boot.”

If you don’t have much time and just need to pick one place or another, if you want something that isn’t touristy at all, try one of my favorites.


Sicily. This is nearby where we were the first time Francesco proposed. The first of 2,000 times. 


I love this list of cities in this Huffington Post article by Sucheta Rawal: Off The Beaten Path In Italy’s Small Town. She covers small villages that are not typical tourist destinations. I could add a lot to this list so I think I will in another post this week. I’ve spent a lot of time in Italy in tiny villages visiting the hometowns of friends or places that Francesco’s family lives or grew up.


If you want a destination that isn’t as touristy as cities like Venice but isn’t completely off of the map you can try some places on this list of Favorite Italy Destinations: Italian travel from Saga Navigator. They also do tours which is an added bonus if you’re looking for that type of thing (I haven’t taken one of their tours but they’re rated well). I’ve been all over Sicily with my husband and it was awesome. It’s one of my favorite travel destinations because it’s so different from the rest of Italy, plus the food is amazing, and it’s just badass. I’ve been to Sardinia for a weekend and I loved it. Probably some of the nicest beaches I’ve ever seen are in Sardinia. I haven’t personally been to the places on the list but the Adriatic Riviera is absolutely on my list of places to go. One of my old roommates went and she loved it. It’s expensive but with AirBNB, and good tour guides, it’s totally doable. I’ve heard it’s an especially romantic place for couples or a great place for groups of friends to unwind.

Where would you recommend that isn’t a typical destination?

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