Italy has quite a few nice cities to visit, and if you just want to go to Italy for the sake of it, and spend months there, then stop reading now. However, if you have 5 days of PTO, and want to maximize it, then keep reading. Even with maximizing your time though, if you can’t spend 10-14 days here, you will just need to accept that you won’t be able to hit up all of the hot spots in one trip.
If you need to prioritize I would do:
A. Historical – Rome, Venice, Pisa, and Pompeii
B. Scenic – Tuscany, Florence, Rome, Amalfi coast
There is certainly some room to overlap (Pompeii is right next to the Amalfi coast for example, and Rome is on both lists), but in general, this should help you prioritize your time if you need it. Italy is one of my favorite countries in the world. Not just for how pretty it is, but also for how friendly the people are, relative ease of getting around, and the food (who doesn’t love carbs right?).
Rome (spend 2-3 days there depending on your love of history)
You need to see the Coliseum, walk around the old city, and really appreciate the seat of power for one of the largest, most powerful, and influential seats of power in history. The whole place is pretty amazing and worth the time. In addition to Roman history, the Vatican should be worth a day of your time as well. So, 1 day for Roman ruins (2 if you’re into it), and one day for the Vatican. At a minimum! If you have the time, another day for travel and hanging out, would also be encouraged.
Tuscany (spend a day here)
One of the most beautiful parts of the world, trek around and visit vineyards, try some wine, walk around some quaint small towns, and spend at least a day here. More if you have the time (and money), but one day and you shouldn’t feel too cheated.
Pisa (spend a day here, at most)
Get the cheesy photo, cross off the bucket list, and be disappointed like the rest of us.
Florence (spend a day, maybe two)
Florence is very pretty, hosts the statue of David, and gives you that Italian city look you’ll be craving (because bar Tuscany, few places give you this).
Venice (spend 2 days here)
Yes, it is crazy crowded, kind of smells, and can be a bit cheesy, but it is worth it. It is a unique city, and a well-deserved bucket list destination.
Milan (Skip, unless you just love fashion) –
Full disclosure, I haven’t been, but I have heard from multiple reliable sources that it is dirty, with little to look at, and more of an industrial city. So, yes, it is famous for fashion, so go there if you’re called to do so, but the rest of you may be bored. Maybe check out some history, but I would recommend not going there just for that.
Isle of Capri (Spend a day here, not necessarily worth staying on the island)
For here, I implore you to take a chance and don’t book in advance (unless you want a sweet yacht, in which case, money shouldn’t be an issue). Wait until you get to the dock, go to the restaurant, and ask them if they have any friends who wouldn’t mind taking you on a tour around the island for $300-$500. We did this and for five people and it was less than the “tours,” plus we got the whole boat to ourselves! vs. a crowded and expensive boat where you have to adhere to their schedule.
Pompeii/Naples (spend a day here, well worth it) –
I last came here when I was about 10 years old and it has left quite an impact to this d
The Amalfi Coast (spend a day here. It is roughly a 3-hour drive from Solerno to Sorrento I believe, but double check)
Another beautiful part of Italy, and certainly worth the drive. I don’t know too much about where to stay and what to do, but take a day to enjoy the scenery, drive the coast, have a leisurely lunch, etc. Pair this with either Capri, or Pompeii, depending on what kind of trip this is for you.
This may be as far south as you want to go though. Just in the interest of time, there isn’t a ton south of here.
Country-level of difficulty – 3/10