Italy is easy to get wrong.
Not because there isn’t enough to see—but because there’s too much.
It’s one of the few countries where trying to “fit it all in” almost guarantees your trip will feel rushed.
I’ve returned to Italy many times, and what I’ve learned is this:
The experience doesn’t come from how much you see.
It comes from how you structure your time.
How I approach planning a trip to Italy
I don’t try to see multiple regions in one trip.
I choose one—sometimes two—and build the trip around that.
That might look like:
- Combining Florence with time in Tuscany
- Bologna, with time, exploring Emilia Romagna
- Or combining Milan with time in Lake Como and Verona
What I don’t do anymore is move constantly.
Because in Italy, every time you change locations, you lose part of the experience.
I return to Italy for that experience. To walk cities early, linger over lunches, and stay long enough to notice what most itineraries miss.
Italy is a country that is made for exploring slowly, and is worth returning to again and again.
Rome
Florence & Tuscany
Bologna & Emilia-Romagna
Milan, Turin & Northern Italy
If your Italy itinerary feels overwhelming
Italy is one of the hardest trips to structure well.
If you’re trying to figure out how many places to include, how long to stay, or how to make it all flow without feeling rushed—I can help you plan it.
My approach focuses on choosing the right places and building a trip that actually feels good while you’re in it.