A family trip to Italy sounds like a dream come true, doesn’t it? Delicious food, a rich history, a warm, welcoming culture: they’re just a few of the reasons to start planning an Italy itinerary.
But if you’re thinking a family trip to Italy is just a faraway dream, think again!
Unlike in the US where food, drinks, and lodging can be expensive in bustling cities, it’s actually quite easy to find affordable alternatives just about everywhere in Italy. Add in budget airlines heading to Italy on a regular basis for about the same price as a cross-country plane ticket, and you’ll find that a 2 week trip to Italy won’t cost much more than a week in New York or San Francisco.
If the idea of planning a multi-city itinerary in Italy sounds daunting to you, don’t fret!
Follow along with our 2 week family-friendly itinerary below and start picturing your family living ‘la dolce vita’ in Italy!
Note: This post contains affiliate links. If you make a purchase by clicking through these links, we’ll be rewarded with a small commission (at no additional cost to you)! Thanks so much for supporting our adventures.
Itinerary for 2 Weeks in Italy with Kids | Mapping it Out
We decided to start our adventure in Milan, ending two weeks later in Rome. We’d have loved to tack on Venice or the Amalfi Coast, but alas, with limited time it meant we had to trim some cities off our wish list.
You could easily adjust this itinerary, swapping Venice for Rome or Milan and the Cinque Terre for Naples and the Amalfi Coast.
This two week itinerary is fast-paced for families with kids, but not so much that it’s overwhelming. You’ll spend the bulk of your time in Florence and Rome, with short breaks in Milan, Cinque Terre, the Tuscan countryside, and Orvieto in between.
Day 1 | Milan
Start your Italian adventure in northern Italy’s largest city. Milan is a great place to start your journey and ease into Italy: it’s a modern city, cheap to fly into, and offers some beautiful sights to see while you get over your jet lag and prepare for more intense legs of the journey.
Where to Stay in Milan, Italy
Brera | Walking distance to the city center, the Brera neigborhood is ideal for those who only have a day to spend in Milan and want to pack it all in. The downside? It’s a hot neighborhood, so staying here even for just one night can be pricey. The Carlyle Brera Hotel is a great option that won’t break the bank.
Isola | For those on more of a budget, consider Isola, a tiny neighborhood wedged in between Milano Porto Garibaldi (the last stop on the train from the airport) and Milano Centrale (the train that will take you out of the city for your next stop). It’s a bit outside the city center, but it’s local neighborhood feel, quaint eateries, and quick access to the city center via the #3 subway make it an ideal place to settle for the night. Consider at stay at Hotel Zara conveniently located nearly the Zara metro station.
What to See & Do in Milan, Italy
- Duomo di Milano | You’ll only have a few hours to see Milan, so if you only do one thing, make it a visit to the Duomo di Milan. The cathedral is a masterpiece of architecture that’s not to be missed.
- Galleria Vittorio Emanuele II | This massive “shopping mall” is one of the largest in Europe, and boasts not only high-end shopping, but some amazing architecture as well.
- Parco Sempione | Visit the Castelo Sforzesco, Milan’s Aquarium, or simply stroll through the park as you walk off the jet lag.
Early the next morning, take the first train out of Milano Centrale towards Montessoro al Mare in Cinque Terre. Pre-book your tickets with Rail Europe to get the best deals.
Days 2-4 | Cinque Terre
Once a hidden gem of Italy, Cinque Terre is now bustling with tourists. But even so, it’s still worth a visit to this unique collection of 5 (cinque) fishing villages along the Ligurian Sea for the hiking trails, expansive views, picture-perfect streets, and fresh seafood straight from the sea.
Where to Stay in Cinque Terre, Italy
Manarola | Deciding where to stay in Cinque Terre can be a tricky question for first-time visitors. We stayed in Manarola, so I may be slightly biased, but I would 100% choose it again and again! It might be because I fell slightly in love with Nessun Dorma, a wine bar perched on the hill overlooking the village. If I could spend every evening there for the rest of my life, I’d be one happy gal.
Vernazza | My second favorite city in Cinque Terre, Vernazza has a lovely little marina that’s perfect for quiet evenings. Vernazza’s train station is also easily accessible from anywhere in town, so it makes bouncing to the other villages a breeze.
There aren’t too many traditional hotels in Cinque Terre (and most that are there are located in Monterosso), so an Airbnb or other private rental is the best way to go. We took a chance on this Manarola Airbnb with not such stellar listing photos, and despite it’s small size, the modern feel and perfect location couldn’t be beat!
What to See & Do in Cinque Terre, Italy
For the full experience, spend a little time in each of the 5 villages, taking in the little treasures that each has to offer:
- Monterosso | Stroll the “new town” and grab drinks or lunch at a seafront restaurant. In the summertime, rent an umbrella and lounge on the beach or visit the farmers market in old town for some fresh produce. And of course, visit the Church of San Giovanni Battista with its black and white marble stripes.
- Vernazza | Grab gelato at Vernazza Gelateria, eat Ligurian Trofie al Pesto as you watch the boats come in and out of the marina, or stroll the narrow alleyways: Vernazza is all about taking it slow! It’s also a great place to hire a boat ride and see Cinque Terre from the water.
- Corniglia | Hike the 365 steps from the train station to town, visit the Chiesa Di San Pietro church, and drink limoncello in the town square. Some bloggers will tell you to skip Corniglia because there’s not much to do. I do not agree! Corniglia is the quietest, most unspoiled of the 5 villages, so for a more relaxed feel, make the hike up to Corniglia!
- Manarola | Walk Via dell’Amore (aka Lover’s Lane) along the cliffside and sip Italian wine during apertivo hour at Nessun Dorma. Don’t miss the playground at the top the hill behind Nessun Dorma, and definitely snap some swoon-worthy sunset photos.
- Riomaggiore | Dip your toes in the marina’s waters, get a photo op of the town at sunrise, and hike up the hill for gelato!
Once you’ve gotten your fill of Cinque Terre, take the local train to La Spezia, where you’ll connect to a regional train to Florence (tip: local Cinque Terre cards can only be bought upon arrival, but you can buy your tickets to Florence in advance via Rail Europe).
Days 5-8: Florence
After spending some time on the coast, you’ll be ready to head inland for some city adventures! While it might seem tempting to make a pit stop in Pisa on the way, I recommend continuing on to Florence now to set up a home base. With all the moving around, it will feel good to be in one place for awhile, and you can easily return for a day trip.
Where to Stay in Florence, Italy
Santo Spirito | I couldn’t recommend the Oltrarno area enough, on the other side of the Arno River. The Santo Spirito neighborhood is just enough removed that you are close to the action without having to be “in it”, away from most of Florence’s busy tourist sites. In return you’ll find it to be a bit more quiet and local. Trust me, Florence can burn you out fast if you haven’t planned some downtime. The Hotel Palazzo Guadagni is right on the corner of the Piazza Santo Spirito and would no doubt make a lovely spot to end your busy days!
What to See & Do in Florence, Italy
- Duomo di Firenze | Of course, how could you visit Florence and NOT visit the Duomo? I highly recommend pre-booking your visit to avoid as much time as possible waiting in lines.
- Palazzo Vecchio | Climb the steps for a unique vantage point of the Duomo di Firenze. (one caveat, children under 6 are not allowed up the tower).
- Ponte Vecchio | Take a walk across Florence’s most famous bridge, window shopping the jewels and gems of the shop owners.
- Piazelle Michaelangelo | Ride the classic carousel for just 2 Euros. 🙂
- Mercato Centrale | Florence’s massive food hall, this is a great place to try a little of everything Italian. You’ll find a mix of locals and tourists here.
- Boboli Gardens | A nice place to picnic or spend a quiet afternoon, the gardens are located behind Pitti Palace (a place you may or may not want to brave with kids, depending on their age). The gardens are expansive with lots of little hidden pockets (think: the gardens of Versailles), and you could spend hours meandering around.
- Day Trip to Pisa & Lucca | If, like us, you feel you must get the obligatory Leaning Tower of Pisa photo, make a day trip out to Pisa! Combined with a visit to the beautiful walled city of Lucca, it’s a nice way to get another taste of Tuscany.
- Day Trip to Siena | Another favorite Tuscan city, spend some time in Siena visiting Piazza del Campo, admiring Duomo di Siena (be sure to pre-book your visit!), or trying a food or wine experience.
Day 9-10: Orvieto
Florence is busy and you’ll likely be tired, so I recommend taking a day or two to unwind before you jump right into Rome. Orvieto is located almost exactly halfway between the two cities, so it makes for an ideal stopping point on your Italy itinerary. We rented a car in Florence and drove the A1 to Orvieto. Driving in the city is nerve-wracking, but doable. If you’re not so brave, you can take the train just as well.
Where to Stay in Orvieto, Italy
Outside the City Walls | Agriturismos dot the countryside around Orvieto, which is a totally underrated wine-growing area. We stayed at Cantina Lapone, an Airbnb on a winery estate. You will need a car to get there, but it’s only a 15 minute drive or so outside Orvieto’s city walls.
Inside the City Walls | If you’re arriving by train, you can take the funicular from the train station up the hill to the old town. Located on the edge of the city, Palazzo Piccolomini is a charming, and affordable, place to base yourself for a short stay in Orvieto.
What to See & Do in Orvieto, Italy
- Duomo di Orvieto | The black and white striped cathedral is the focal point of Orvieto and not to be missed!
- Torre del Moro | Climb the 250 steps to the top of the clocktower and be rewarded with 360 degree views over the city.
- Market at Piazza del Popolo | This sprawling farmers market takes place each Thursday and Saturday from 8 am to 1 pm.
- Wine Tasting | If you have a car and can make it outside the city walls, experience a tasting at one of the many vineyards surrounding the city. Madonna del Latte and Decugnano dei Barbi are two of the most popular!
Day 11-14: Rome
All roads lead to Rome, so it’s fitting that that’s where we end our itinerary. Take the train or drive your last leg of the journey to Italy’s magnificent capital city. You’ll find there’s no shortage of sites to see in Rome, so with just 4 days, pick your favorites and get to exploring!
Where to Stay in Rome, Italy
Trastavere | What used to be a local secret of Rome, Trastevere is far from it these days. Sitting across the River Tiber from Rome’s busy tourist sites, Trastavere might be a bit out of the way but is well worth the hike for it’s quiet streets (by day – nighttime is a different story!) and abundance of eateries! Sweet Inn Trastavere offers a collection of 4 modern apartments.
Jewish Quarter | Just over the river from Trastevere is the Jewish Quarter, a recently revitalized part of Rome that’s been flooded with delicious cuisine in recent years. It’s a bit closer to sites like the Colosseum or Campo de’ Fiore (or everything in Rome, really). Hotel Monte Cenci is a great hotel option in this area.
What to See & Do in Rome, Italy
- The Vatican | While we didn’t make a trip the Vatican on our visit (that’s what happens when you accidently plan to be in Rome over Easter…oops!), it still tops most families’ Rome bucket lists. Be prepared to spend a full day between St. Peter’s Basilica, the Vatican Museums, and the Sistine Chapel. This is one place where skip the line tickets are well worth the extra expense.
- Colosseum & Roman Forum | Of course, when in Rome you must see the Colosseum, so book your visit early here too to avoid the lines (or pro tip: go first thing in the morning!) Your tickets will give you entry to both the Colosseum and Roman Forum, so be sure to plan enough time for both.
- Campo de’ Fiore | This open air market is a great place to grab a morning snack, load up on picnic essentials, or simply people watch from atop the fountain.
- Trevi Fountain | Toss in a penny (or 2 or 3) with a wish. Just be prepared to push your way down to the fountain as it gets quite packed! Afterwards, head over to Il Gelato di San Crispini for some gelato.
- Spanish Steps | Another great place for people watching. Grab some 4 Euro pasta to go at Pastificio, just a few blocks away.
- Villa Borghese | Wander the lavish grounds or rent a boat for a ride around the scenic lake.
Have you been to Italy? What was your favorite city?
Liked this Post? Pin It!