There’s a question I hear constantly — from people emailing me about custom tours, from strangers in Facebook travel groups, from friends who know I live here and figure that makes me some kind of oracle. (Truthfully, I kind of like that last bit.) The question is some version of: I have ten days. Is it crazy to try to do Rome, Florence, Venice, and maybe the Amalfi Coast?
The answer is yes. It is crazy. And not just crazy, but exhausting.
Italy does this to people. You’ve carved away the vacation time, you’ve decided to spend the money, and when you finally sit down with a map to plan the trip, everywhere looks so…reachable. Rome to Florence is nothing. Florence to Venice is a quick train ride. And the Amalfi Coast is just down there at the bottom, waving at you. The next thing you know you have six destinations in nine days and a color-coded spreadsheet, and it all looks completely reasonable until you’re actually there, dragging your suitcase up a near-vertical cobblestone street at 11pm and questioning all the life choices that led you to this point.
My colleague Laura Itzkowitz — she writes The New Roman Times and knows the country as well as anyone I’ve met — and I sat down together recently to talk through the actual math of how many places you can see in a given amount of time, and more importantly, how many you should. We had a lively back-and-forth about it. The short version: whatever number you’re currently thinking, subtract at least one.
The thing nobody budgets for
Here’s what an itinerary doesn’t show you: the morning you arrive somewhere new and spend two hours just figuring out where things are. The afternoon your train is delayed and you arrive at your hotel after dark with no idea where to eat. The day you wake up jet-lagged and your ambitions for the Uffizi quietly turn into a long lunch and a nap — not a wasted day, but a day of rest that you need.
None of that is a failure, but all of it takes time. And if you’ve scheduled yourself into a different city every two nights, there’s no room for any of it.
One week: two places
Be honest about what a week actually is. You arrive tired on your first day, so can’t schedule anything too demanding. The last morning you’re packing and getting to the airport. You have somewhere around four or five whole days where you’re able to do more than maybe one thing. One of those will involve moving between your two destinations, so there goes a half day right there.
So really, you may not want to hear it, but two places is the most you should try to fit into a week.
What tends to work well is pairing a city with something that has a slower rhythm — a stretch of countryside, a hill town (maybe a tiny Umbrian hill town, cough cough), or a beach. That’s not because two cities can’t be done in a week, but because both will feel like you barely got started. Give yourself Rome and then come up to Umbria, or go to the Castelli Romani near Rome, or head to the Tuscany seaside in shoulder season. That way, you get city energy, then somewhere to exhale.
Ten days: resist the temptation to pile on stops
Ten days feels like real freedom, and it is — within reason. Three destinations is fine, as long as they make geographic sense together and at least one of them isn’t someplace where you need to spend all your time in museums just to feel like you’ve done it justice.
Sicily, for instance, works well in ten days: one base on the eastern side, one on the western side, day trips from each. Puglia is another great fit — the Valle d’Itria for a few days, then down into the Salento, Lecce as a second anchor. These are trips built around staying somewhere and radiating outward, rather than dragging your bag to a new place every other night.
Laura mentioned during our conversation that she’d recently helped someone plan a trip with three days in Rome and six days in Tuscany — and the client had originally wanted to add Florence to the mix. She took it off the list, and instead enjoyed an unrushed stay in the Tuscan countryside.
Two weeks: still not as long as it seems
Believe it or not, a two-week vacation in Italy is when people tend to wear themselves out the most. Because two weeks feels like it should be enough time to do everything (and to keep everyone in your travel party happy, but that’s another topic for another day). It isn’t, but more importantly, it doesn’t need to be.
Two weeks actually is enough time to see Rome, Florence, and Venice — the holy trinity of first-timer itineraries. It’s doable; it’s just not relaxing. If those three cities are non-negotiable for you and your party, then plan accordingly. Give yourself plenty of wiggle room on your arrival day in any of those cities, to allow for late trains, mixed up directions, and any sorts of things that can go wrong and sap your energy on a travel day.
If you really want to go nuts, you could even work in a fourth stop — a few days in Tuscany, a stretch of coastline, a couple of nights in Umbria. You’ll get a solid introduction to each place, though I’m willing to bet you’ll go home needing another vacation.
The only way two weeks in Italy doesn’t leave you depleted is if you treat the two weeks as two distinct chapters. Use the first week to move around and do the big sightseeing — two cities and their museums and monuments. Then use the second week, or at least a generous chunk of it, to stop. Pick somewhere, unpack your bag (this is important — unpacking is a psychological signal that you’ve actually arrived), and stay. Take long walks without a destination. Eat lunch without checking the time. Let a place start to feel a little bit familiar.
That second chapter is what you’ll remember the most fondly.
The truth bomb: there’s never enough time in Italy
In a single trip, you’re not going to see everything in Italy you want to see, whether that trip is a week, two weeks or a month or more. (Case in point: I’ve lived here for 17 years and I still haven’t seen wide swaths of Italy.)
So before you finalize your itinerary, think about the reasons you want to come to Italy. How do you picture it in your mind? Now look at the schedule you’re building. Is there room in there for that picture to actually materialize?
Laura and I have another webcast coming up on May 28th — this one’s called Smart, Not Scared: How to Travel Safely in Italy. We’ll be talking through practical ways to keep yourself and your stuff safe while you travel, without turning the whole trip into an anxiety exercise. It’s at 12:30 pm EST / 6:30 pm CEST — here’s the sign-up link: https://mailchi.mp/villaggiotours/smart-not-scared-how-to-travel-safely-in-italy
And if you’d like a head start on planning a trip that doesn’t leave you exhausted, my free guide “5 Roadblocks to an Authentic Italy Trip” is waiting for you at villaggiotours.com.