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I have built this Italy itinerary with kids about six times now, on paper, at the kitchen table in Long Grove, usually after Lochlan has gone down and I have told myself I am only going to look at train times for ten minutes.
Every version got shorter. The first one had five cities in it. The one I am actually going to book has three, and two of those are places I would be happy to never leave.
Here is where it landed, and more importantly, why. I have been to all of these places. I have not been to any of them with a two-year-old, so what follows is a plan rather than a report, and I will tell you where I think it might break.
The short version
Nine days, three bases, no backtracking. Fly into Venice, take the train to Florence, take the train south to Sorrento, fly home out of Naples. Three nights in each place.
That is two travel days inside the trip, both of them trains of under four hours, both of them in the middle of the day. Everything else is spent somewhere we have already unpacked.
If you want the one-line version of why: a toddler does not care that you saw Rome. A toddler cares whether the bed is the same bed as last night.
Why this order
North to south, for three reasons.
The first is jet lag. Coming from the Midwest you land in Europe destroyed, and Venice is the kindest possible place to be destroyed. There is nothing you have to do and no traffic to cross. You can walk out of your door, get on a boat, and that is a full and successful day.
The second is that it ends at the beach. Day eight of any trip with a small child is not the day to be climbing a bell tower. Ending in Sorrento means the last stretch is swimming and ferries and eating outside, which is the part everyone will actually remember.
The third is purely practical. Flying into Venice and out of Naples costs about the same as a round trip into either one, and it saves a whole day of going back the way you came. Look for it as a multi-city fare rather than two one-ways.
The flight, which is the part I am dreading
Chicago to Venice is a night flight of about nine hours, usually with one stop. There is no version of this that is pleasant and I am not going to pretend there is.
What I have decided: we book the overnight rather than the daytime flight, even though the overnight is harder, because landing in the morning and pushing through to a normal bedtime is what resets everyone fastest. We pay for the seat rather than flying him as a lap infant, because at two he is too big to sleep on me and a seat he can lie across is worth the money. And we build in that first day of nothing, so that if the flight goes badly the trip does not start in a hole.
I have an autoimmune disease, and the honest piece of this is that I cannot do the push-through-and-be-fine thing that I used to do. A day of nothing at the start is not a luxury in this plan, it is the thing that makes the other eight days work.
Days 1 to 3: Venice
Land at Marco Polo, take the boat in. Do not take a taxi to a car park and then a boat. The Alilaguna public water bus goes from the airport into the city and it is both cheaper and the better first hour of the holiday.
Day 1 is nothing. I mean that as a plan. Get to the apartment, go find lunch, let everyone sleep when they sleep. If anyone is upright at five in the afternoon, walk to the water and watch the boats.
Day 2 is St Mark’s Square early, before the day trippers land, and then the vaporetto down the Grand Canal for the length of the line. It costs a few euro and to a two-year-old it is a very long and excellent boat ride. Afternoon back at the apartment.
Day 3 is Burano. Forty minutes out across the lagoon, a village of bright painted houses, and the thing that matters more than the colour is that it is flat, quiet and nobody is in a hurry. Murano is on the same route if you want the glass, though with a toddler I would pick one island and not two.
Dinner all three nights is cicchetti, the small bar snacks on bread that you can eat standing up at five in the afternoon. This is the single most useful thing about Venice with a small child and it solves the eight o’clock dinner problem completely.
If you want the full version of what I would do here, it is all in my Venice travel guide.
Days 4 to 6: Florence and Tuscany
The train from Venice Santa Lucia to Florence Santa Maria Novella is about two hours. Book it a few weeks out and it is cheap. Book it the day before and it is not.
Stay in the Oltrarno, the quieter residential side south of the river, not in the middle of the north side. You can walk over to everything in fifteen minutes and then walk back to somewhere that is not full of people.
Day 4 is arrival and the neighbourhood. Mercato Centrale for lunch, because everybody picks their own thing and no one has to sit still through four courses. Evening walk over Ponte Vecchio.
Day 5 is the one real sightseeing day. The Duomo from the outside, the piazzas, and then Piazzale Michelangelo for the view. It is uphill, which is worth knowing before you set out pushing a stroller, and there is a bus that goes up if the legs have run out. I am not booking the Uffizi. I have been, it is extraordinary, and it is not a thing to do with a two-year-old.
Day 6 goes out of the city. This is the day I would rent a car for, just for the day, and drive down into the Val d’Orcia or over to Siena. Tuscany is the part of Italy that is actively better with a small child, because it is fields and animals and long lunches outside and nobody telling anyone not to touch anything. An agriturismo lunch runs long and that is the point.
My Florence guide and the things to do list have the rest of it.
All of this is in my Italy for Families guide too, if you would rather have the whole thing in one place than rebuild it from a blog post. It is a PDF with the full 9-day itinerary laid out day by day, plus a “with kids” section for Florence and Tuscany, Venice, Sicily, and Sorrento and the Amalfi Coast.
Days 7 to 9: Sorrento and the coast
This is the long travel day. Florence to Naples is about three hours on the fast train, then the Circumvesuviana along the coast to Sorrento for another hour. The second leg is a local line and it is not glamorous. It is also the simplest way to do it and it ends at the sea.
Day 7 is the travel and then not much. Sorrento is small enough to cross on foot in twenty minutes, so get in, find Piazza Tasso, and walk down to Marina Grande for dinner at the water. The fishing village down there has family-run places that are happy to feed you at seven.
Day 8 is Pompeii, twenty-five kilometers back up the line, and it has to be early. The site is open stone with almost no shade and by eleven in the morning it is radiating heat. Go at opening, do two hours, come back for lunch and a nap. Pompeii is also the rare ancient site that works with a small child, because it is outdoors and flat and you can let them walk.
Day 9 is the ferry. Capri if you want the island, or down the coast to Positano and Amalfi from the water. I would take the boat over the road every time. The Amalfi Coast drive is spectacular and it is also a narrow cliff road with switchbacks and summer traffic, and a carsick toddler on that road would end the holiday on a sour note.
Fly home from Naples, which is an hour back up the line.
What we are booking in each place
Apartments in all three, and the same three requirements every time: a bedroom with a door that closes, a washing machine, and somewhere within a five-minute walk to buy milk and fruit.
The door matters more than anything else on that list. In a single hotel room your evening ends when the toddler goes down at seven, and nine nights of sitting in the dark on your phone is not a holiday. A one-bedroom apartment means you get your evenings back, and it is usually cheaper than a hotel room that sleeps three anyway.
The washing machine means we pack for four days rather than nine, which matters when you are also carrying a stroller, a car seat and a child through two train stations.
In Venice I would look at Cannaregio or Dorsoduro rather than right by St Mark’s. In Florence, the Oltrarno. In Sorrento, anywhere within ten minutes of Piazza Tasso, and check how many steps there are down to the water before booking, because some of those cliff properties have a lot of them. I have gone through all three neighbourhoods properly in where to stay in Italy with kids.
Where Sicily fits
It does not, in nine days, and I want to be straight about that.
Sicily is in my guide because it is one of the best parts of Italy and because plenty of people have two weeks rather than nine days. If you have fourteen days, drop Venice or drop Sorrento and give Sicily five nights based in Taormina. If you have nine, adding it means a flight in the middle of your trip and two more hotel check-ins, and that is the trade I am not willing to make with a toddler.
What I’d skip
Rome, which I know is the controversial one, and I have written out the full reasoning for that separately. The short version is that Rome is big and hot and most of what you came for is a queue in the sun.
I would also skip the day trip to Cinque Terre from Florence. It looks close on a map and it is a long day of trains, crowds and stairs cut into a cliff. With a stroller it is close to unworkable.
And I would skip trying to add Milan because the flight was cheaper. A cheap flight into the wrong end of the country costs you a day at both ends.
Questions I get about an Italy itinerary with kids
Is nine days enough for Italy with kids?
For three places, yes, comfortably. For the Rome, Florence and Venice circuit everyone sells you, no, not with a small child. Nine days split three ways gives you two full days in each spot after you take out arrivals and departures, and two days is enough to stop feeling like a tourist.
Should we rent a car?
Not for the trip. The three bases are connected by train and historic centers restrict traffic anyway. Rent one for a single day in Tuscany and give it back. Parking in Florence and Sorrento is a problem you do not want to own for nine days.
Do we need to book trains in advance?
The fast intercity trains, yes, because the price climbs steeply as the date approaches. A few weeks out is fine. The local Circumvesuviana to Sorrento is not bookable and does not need to be, you just turn up.
What about naps?
Built in. Every day in this plan has the afternoon free, and that is not an accident, it is the entire reason the itinerary only has three stops. Mornings out, afternoons back at the apartment, evenings easy.
Which base is the best if we can only do one?
Sorrento, with ferries and Pompeii and the coast all reachable from it, and the whole town walkable. Florence second, for the day trips into Tuscany.
Is it worth flying into one city and out of another?
Yes, and it is the single change that improves this itinerary most. A multi-city fare into Venice and out of Naples usually prices close to a round trip, and it saves you a whole day of retracing the country. Search it as one booking rather than two separate one-ways, which is where it gets expensive.
How much should we budget?
Less than the equivalent trip to France or Switzerland. Apartments are good value, trains are cheap if booked ahead, and eating the way Italians eat is genuinely inexpensive. I am going to write the real numbers up on their own once I have booked ours.
If you are weighing Italy against somewhere gentler for a first trip abroad, the Portugal version of this itinerary is the other one I built this year, and Portugal is the easier of the two.
This itinerary assumes May or late September, which is when I think Italy works best with a small child. My reasoning for that, month by month, is in the best time to visit Italy with kids.
I will update this once we have actually gone and I know which parts of it I got wrong. There is more on the country in the Italy archive.
