Our June/July 2024 2-week trip to Italy was my 8th visit to the country, but the majority of those were “single girl” trips with friends, pre-kids. Planning Italy this time, with 8 and 9 year old daughters, required lots of gelato stops, a sheep farm visit, site tours specifically for kids, cooking classes and an extended stay in Tuscany.
In this post, you’ll find walkable itineraries highlighting interesting sites and piazzas geared pace-wise and distance-wise for kids 7 and above in Rome and Florence. We didn’t hit EVERY site. This was intentional. For example, while I’ve toured the Vatican twice, climbed into the catacombs and experienced Mass in Latin, I made a decision to omit this based on my daughters’ attention spans and interests. We’ll return when they’re older (12 yrs+) and include this plus additional museums.
My planning timeline for this summer trip:
- Book flight and hotels/lodging 5-6 months before travel
- Book museum or site tours 3-4 months ahead as well as any popular restaurants
- Book transportation from airport to hotel (through hotel) plus trains (www.omio.com) or rental car (various) 2 months in advance
ROME
The only hiccup on the LAX-Munich-Rome flight occurred at the LAX airport where we had to escalate to a Lufthansa supervisor to get re-assigned the same Economy seats we’d pre-selected and paid $100 per person for online months prior to the departure date. Travel tip: United’s Star Alliance partners do not automatically have knowledge of nor honor United Mileage Plus status for priority seat selection, check in, security or boarding. Lufthansa in particular treated us much better when we showed our Platinum cards on our United app (later downloaded to our Apple Wallets for easier access) vs just viewing our ECONOMY tickets. There is a hierarchy and if you have status, show it early and often! And yes, despite Platinum United status, we still had to pay Lufthansa for the ability to choose our Economy class seats.
We arrived in Rome at 5:30PM, grateful for pre-booking a car and driver (80 euros one way) through our hotel, the Hotel Savoy. FIRST THING our daughters noticed when we exited the airport: smoking. Seemingly everyone smokes in Italy still, including the driver the Hotel Savoy sent for us. The car smelled!
I choose to book the Hotel Savoy because of location and the ability to book two hotel rooms a night for 3 nights for “free” using my Bank of America Visa credit card points. I assumed this hotel was related to the Hotel Savoy in Florence. It is NOT related and I should have known that based on price. It IS however located in the quiet and safe Ludovisi neighborhood, a 5 minute walk to the southern entrance of the Borghese Gardens and a 10 minute walk to Trevi Fountain. The Italian architecture rooms were air-conditioned and the beds were relatively comfortable. The staff was very helpful and while we walked everywhere 85% of the time, the front desk was quick to order cabs for us when requested. “Major” hotel chains in the same neighborhood include the Westin, Marriott and Sofitel. www.savoy.it
Day One (half day)
With a mission to stay awake until at least 9PM, we unpacked, showered and walked 25 minutes to a restaurant I’d read about in Time Out online called Alle Carrette in the Monti District. We wanted excellent pizza, fast service and cheap prices and Alle Carrette delivered on all 3, plus our waiter loved the kids and was very entertaining. The restaurant doesn’t have a website, just a Facebook page and fabulous reviews online. It was the BEST way to initially experience Italy, though the fastest route I’d mapped on Google didn’t take us by any piazzas or famous Italian sites…it did take us by the Sephora which my daughters are obsessed with! We kept walking and we stayed up until 10PM!
Day Two – 9.4 miles; 20,440 steps
I shared a room with 9 year old, Charlotte, who was awake about 8AM ready for adventure. Steve and Emmeline, the 8 year old, in the room next door, were still asleep. Charlotte and I set out on a quest to find eggs for breakfast (Italians typically just eat breakfast pasteries) in our neighborhood and found Rosemary Terra e Sapori on Via Modena. It’s an adorable café where Charlotte had her first decaf espresso. She did not love it. I had the delicious international breakfast and we got to see the American Embassy, the pretty Fountain of Moses near the St Regis Rome hotel and the Piazza de la Repubblica on our 12 minute walk. www.rosemary.bio
We picked up Emmeline and Steve at the hotel, and set off on a day of mainly unscheduled adventure.
In addition to Google maps, which is my go-to for anything navigable, I also buy a Streetsmart Guide when traveling to major cities outside the US. The Rome version gave me a “big picture” view of the city and an understanding of neighborhoods, proximity between them, their historic sites and museums AND helped me research restaurant and gelato stops nearby. Travel tip: Why research lunch restaurants? Why not just meander and assume you’ll find somewhere great? Because I hate getting caught in tourist traps. I’d rather have a loose plan of a few good options in each area we are visiting so that when the kids suddenly cry out “I’m starving,” we aren’t stuck popping into an overpriced, mediocre spot.
We began day 2 by exploring the Borghese Gardens, an 8 minute walk from the Hotel Savoy. Also near Borghese Gardens are the Westin and Marriott hotels. I picked a location near the Gardens because my daughters love to run and play and explore and, being the 3rd largest public park in Rome, the Gardens provide 197 acres to do all of the above. There are bike rentals of various types; playgrounds; merry go rounds and carnival rides; street performers; a zoo, sculptures; ponds; and museums. Though I’ve been twice before, we did not buy tickets to the Borghese Museum with the kids. I picked only a few museums on this trip to avoid burn out!
After an hour of exploring, we walked to the middle of the west side of the Gardens to the viewing platform above the Piazza de Popolo. We took the obligatory family photo and headed down the long pathway to the Piazza.
It was hot – like 85 degrees hot – in Rome that day. The gelato stop in the Gardens wasn’t enough to cool the kids down so we randomly entered the Leonardo de Vinci museum on the Piazza de Popolo looking for air conditioning and a bathroom and found a gem. The girls LOVED and we loved learning more about Leonardo, his inventions, his art, his music…it was a fascinating museum and very interactive. No need to buy tickets in advance or have a guide. www.leonardodavincimuseo.com
From there, we walked across the Tiber River on the Ponte Margherita to the Trastevere area. My goal was Castel Sant’Angelo. We got a picture in front, but the kids didn’t appreciate the architecture much given the heat.
From there, we walked through the Campo de’ Fiori marketplace where the girls were very intrigued by the food, olive oil and purses on display. Lunch was around the corner from CdF at Roscoli and scheduled for 2:30PM. The reservation was made 3 months in advance. Definitely go here! People are packed in tightly which isn’t great for kids under 5, but ours were at a good age to appreciate the food and the ambiance. They have take-out and delivery as well! www.salumeriaroscoli.com. FYI…there is also one in NYC.
After our 1 ½ hour lunch experience, we walked to the Pantheon…didn’t have advanced tickets and too crowded to get in, but doubtful the girls would have been intrigued by it at this age. We did go to the underground colosseum at Piazza Navona to see ancient ruins. No need for a tour here, it’s self explanatory.
Then we hit the Trevi Fountain which was very crowded at this time of the year. Took the requisite picture throwing a coin into the fountain and walked about 10 minutes back to the hotel for room service dinner. The whole family was pretty wiped out, but we saw A LOT of Rome in one day!
Day Three – 12.22 miles; 29, 715 steps
Due to the heat, we cabbed 15 minutes to the Colosseum for our Rome Private Guides 3 hour Colosseum and Ancient Rome (Palatine Hill and Forum) private tour geared to kids, starting at 9:30AM. Our tour was 650 euro for our family and I believe it was worth it…though we didn’t get to go underground to see where the animals were held (supposed to be cool). Our guide spoke perfect English, was full of “fun facts” interesting to adults and kids AND she was very conscious of the heat and would lead us to shady spots to explain the history of Palatine Hill, Rome’s rulers and the gladiators. The group also has private tours of the Vatican and areas of Florence as well. I highly recommend them! www.romeprivateguides.com
After our tour, we grabbed lunch and gelato in the Monti neighborhood next to the Forum. There are so many places to choose from…we went to Trattoria al Tettarello and besides the pizzas we ordered, the lunch highlight was watching a huge Italian family celebrating a birthday at the table next to us. They ordered mounds of burrata and tomatoes, prosciutto and melon and other delicious looking dishes I swear I didn’t see on the menu and ate family style. I wanted to join them!!!! They don’t have a website, but they do have a Facebook page. We just walked in.
We walked north, through the Piazza Venezia and admired the Monument to Victor Emmanuel II (aka “the wedding cake”) and made our way to the Via del Corso. Travel tip: Doria Pamphili museum is nearby and it’s lovely, but we didn’t stop because of our daughters’ ages and attention spans. Eventually, after stopping again for gelato AND at Louis Vuitton, Burberry and Prada, we arrived at the Spanish Steps. We climbed the steps, took pictures at the top…climbed back down, took pictures at the bottom, drank water from the fountain in the boat sculpture (it’s safe) and headed back to the hotel to freshen up for dinner.
We walked to dinner at Poldo e Gianna Osteria, near the pretty Parliament building. It was an excellent pick for our last night in Rome: fancy, great Italian wine selection and fresh pasta. I booked this restaurant a month in advance. www.poldoegianna.it
Our walk back to the hotel took us by the Trevi Fountain again. It’s so beautiful when lit up at night, but there were still hundreds of people there and we didn’t stay more than 5 minutes.
Day Four (half day)
One our last day in Rome, our train to Cortona (Tuscany-next leg of our vacation) didn’t leave until 3:10PM. BUT, we cabbed to a luggage storage place across the street from the Rome Termini train station at 8AM and dropped off our stuff because we had plans for the day in Rome. I wouldn’t recommend the storage place we picked. I feel like they may have been trafficking drugs or human out of there! Seriously…very sketchy. They put our luggage in the locked closet of an “everything” store…batteries to men’s underwear featuring the David (IYKYK). It was there when we returned, but I did not feel great about it. Use Stow Your Bags nearby or Deposito Bagagli in the station itself. Travel tip: go to Mercato Central in Termini if you have time. It’s a high quality food hall with alcohol. www.mercatocentrale.com
We then cabbed to Baylon Café in Trastevere for an American Italian breakfast (meaning: eggs are on the menu!). Trastevere is known for its student population…lots of study-abroad kids as well as Italian college kids hang out here and the bars and restaurants are very cool. This was the area I spent the most time in as a single person. With the kids, breakfast in Trastevere was great and they appreciated American-leaning options (eggs!). Baylon Café is a bar too in the afternoon…just Google it. No official website.
Our next stop was 2 blocks from the restaurant: Eating Europe’s Trastevere for Foodies and Pasta Making Tour. This tour is geared for families and we were paired with a New Jersey family with two daughters around the same age as ours. The girls became friends in less than 10 minutes and thoroughly enjoyed hanging out and walking around Trastevere tasting various items. Our Eating Europe Guide was also a father of two and very entertaining. Making pasta was the highlight of the Rome portion of the trip for the girls. They each got to make their own ravioli and linguine pasta. This was our 3rd EE tour as a family (Paris, London and now Rome) and they continue to be consistently great! www.eatingeurope.com
Sadly, after 3 ½ hours of eating and making Italian food in Trastevere, we had to leave Rome…we cabbed to the sketchy luggage place, retrieved our bags and got to Termini in time to grab a quick macchiato. I had booked us in Premium class using Omio for $195 total. Premium means you pre book seating. We had a table in between us and the girls did schoolwork, colored and read during the 2 hour direct trip to Florence. We then had to jump on another train (not as easy to find, but people were helpful at the station) to Cortona. The local train took 1 hour to arrive in Cortona. Because I needed a 3-ish departure time from Rome, we didn’t go the most efficient route to our destination! www.omio.com
CORTONA – Providence of Arezzo, Tuscany
Cortona is the hilliest of the Tuscan hill towns (1,621 ft), located near Lake Trasimeno and is the town where the book/movie Under the Tuscan Sun was based and filmed. We found Cortona not through movie fandom, but through a charity auction. “7 nights in a Tuscan Hill Town” was the live auction prize and we won the bid. Hill Town Tours helped guide us a bit pre-vacation and would have provided more help had I let them, but I wanted to research the town on my own. www.hilltowntours.com One thing I wish we knew about before we arrived: Epic Bike rental in Cortona. Check out the website for excursions and yes, they have family friendly bikes. www.epicbike.it
We arrived at about 6PM and took the free shuttle up, up, up, past small shops and big villas, about 15 minutes to the town of Cortona. Our apartment was easy to find, but we made an entrance, pulling our carry-on luggage across the cobblestones along the “main drag” (Via Nazionale) of Cortona, down a hill and around the corner to our front door. The town limits cars and the streets are extremely narrow; definitely a pedestrian-focused village. It is the definition of charming: outdoor seating along the streets and in the piazzas, Tuscan stone architecture, flowers draping doorways, small-town neighborhood feel and warm greetings from locals.
And then we had dinner at Beerbone Art Burger! The kids loved it: pizza and burgers. I felt like it was a “fail” to sacrifice charming for convenient…but after settling in and exploring a bit, it was already 9PM and the kids were cranky. No website, but you can Google it. I hate to even mention it, but the food was very American and the kids were craving that.
Day Two
Italians aren’t big breakfast eaters. And Cortona only has a couple options for it. I found Café Vittoria and basically stuck with that one for a macchiato and croissant each morning. Literally, it was a 5 minute walk from our apartment, but, after a day of exploring Cortona, we realized it is a SUPER SMALL town. Along our vertical hike up to the highest point in Cortona, the Fortress of Girifalco (pretty much ruins, but there are art exhibits there periodically) we stopped by the Basilica of Saint Margaret of Cortona. No tour guide…just explored the church and found a dead body. Yep, I Googled it and on the altar is very much the undecomposed body of the Saint who died in 1297. The girls were fascinated and freaked out. www.traditionalcatholic.co
Post our hike, we had a fantastic lunch overlooking the main Piazza Pescheria at Ristorante La Loggetta…with a bottle of white wine to drown out the dead body images. www.laloggetta.com
After lunch, we walked around a bit more, checked out the Dali exhibit, found the serene Parterre Park and watched some boys play aggressive street soccer. We then stopped at La Botteghina for a little apertivo. Apertivos became my favorite in Cortona and lots of restaurants and wine/cheese shops offer them. Little salami, little cheese, little wine at a cheap price. What’s not to love?!?!?! No website. Just Google. It’s at 27 Via Nazionale.
For dinner, I had made a day-of reservation at Osteria del Teatro. Again, everything is walkable, though this one is up a pretty steep path. The restaurant feels like you’re in someone’s home. We all had homemade pasta and, to be “healthy” -because we barely had any vegetables all vacation- I ordered a side of grilled marinated vegetables…amazing! I will warn you. The girls wouldn’t go to the bathroom there because it was filled with creepy old dolls. Even next to the toilet paper. Everywhere. www.osteria-del-teatro.com
Our final stop of the night was Dolce Vita for gelato back on Via Nazionale. Good thing we ate all those vegetables!
Day Three
A winery luncheon and tour was included with the charity auction package for Cortona so we booked ahead through Hill Town Tours. The driver they arranged for us picked us up right outside our apartment and took us to La Braccesca in Montepulciano, about 25 minutes drive. Right away, we could tell this was more like the Robert Mondavi of Montepulciano than a small family winery. The tour was interesting and the grounds were beautiful, but it just wasn’t what we were hoping to experience. The lunch looked better than it tasted. We didn’t buy any wine. The girls were interested in the wine tasting and we let them have some sips of wine, but completely uninterested in the food. They did cartwheels on the lawn and found a couple boys their ages to play with outside. www.labraccesca.com
We came back to the apartment, did laundry (washing machine, no dryer), went to a wine store in town and bought actual small production Cortona wine and got ready for dinner.
Dinner was at Ristorante al Tocco, the fanciest and best restaurant in Cortona. The staff was entertaining and the 4 course prix fixed meal was delicious and creative, but this isn’t a “family” place. We don’t need Beerbone, but it was also a waste of money to pay for our kids to eat simple pasta. I wish they had more sophisticated palates, but alas, not yet. Definitely worth going with adults! www.ristorantealtocco.it
The Eurocup Soccer tournament occurred during our trip and we quickly became soccer super fans. Sottovoce bar in the Via della Repubblica piazza was our go-to spot for match nights…and this was the night we discovered this little gem and their Aperol spritzs.
Day Four
On this day we scheduled the Val D’Orcia Wine and Cheese Tour through Tuscan Private Driver and it was worth every penny of the 480 euros I paid for it. We left from our apartment at 9:30AM for a 7/8 hour day trip. Travel tip: drivers matter! This one was memorable. Not only did we get to tour a small batch winery and have lunch at the sheep farm, per the pre-booked agenda, BUT he also took us to the house where Gladiator was filmed, to the town of Pienza for gelato, to the town of Montepulciano where scenes from Twilight: New Moon were filmed and to the Under the Tuscan Sun house back in Cortona. He was entertaining and great with kids. www.tuscanprivatedriver.it
For dinner that evening we tried the “best-idea-ever” wine/food window a minute from our hotel: La Dispensa del Preludio. Get the prosecco porchetta special, served through the window in the street by a smiling Italian guy. It’s the best. And VERY filling. The kids were full from snacks earlier. http://www.ladispensa.it
Day Five
This was a failed plan that became a memorable day. Lake Trasimento is a 30 minute drive from Cortona and is the largest lake in the Umbria region with a 49 mile surface area. My husband Steve mapped a train route that would take us to a good area for kids, but first we had to get off the Cortona hill and down to a different train station from the one we’d arrived at. We needed to catch a certain bus that would take us on a local route for an hour to the 10 mile-away train station. I thought this was inefficient so I waived off the bus and called a cab direct to the lake. The fare seemed cheap for the distance and after driving for about 5 minutes we realized the miscommunication. He drop us back off where he picked us up…and bathing suits on and water-ready, we decided to try out Cortona’s newly refurbished public pool instead. It was lovely, cooled everyone off and we spent the entire day there. There’s a snack bar with cocktails, a restroom and locker room. Bring towels and bathing caps.
The wine tasting with Cortona’s “orange haired wine woman,” as described by friends who’d visited the town a month prior to us, was something we had to experience. And she was funny, enthusiastic, kind and kid-friendly. I’d estimate we tried 14 different wines…but at some point along the journey, I lost track. The girls devoured 2 plates of her cheese bread while we enjoyed the animated stories of her life and the origins of the wine we tasted.
Day Six
I pre-booked a 30 minute train ride to the medieval city of Perugia in Umbria and we explored that town on foot and using Perugia’s MiniMetro called the Fontivegge. This little train was a huge highlight for the girls and took us from near the train station to the city center. The town is known as “City of Chocolate” for the Baci Perugina. We didn’t tour the Casa del Cioccolato. You have to book in advance and it’s outside the city. www.perugina.com
We ate, shopped, toured the National Gallery and ate some more. It’s a good spot to visit with kids when staying in a nearby village. When we arrived back in Cortona we walked ALL THE WAY from the train station to the village. I was so proud of our daughters!!!! It was 1,000 degrees and very vertical, but we made it and came back a parade in the main piazza.
That night, we enjoyed watching another EuroCup match at Sottovocce, at a table reserved specifically for our daughters.
Day Seven
On our final day in Cortona, we explored the city again, focusing on anything we felt we might have missed. My husband had friends in Cortona from Orange County, CA staying in a villa with a pool. We spent the afternoon swimming, drinking wine, picking fresh fruit from the villa’s trees and swapping travel stories.
Our final dinner was at La Dispensa and we said goodbye to our favorite jolly Italian from the wine window.
FLORENCE
Day One
A friend recommended Villa de Medici, Autograph Collection because of its city-center location and the pool. She was spot on! I used American Express points so a 2 bed/1 bath room was free. www.marriott.com
After a 1 hour train ride direct from Cortona to Florence, we were ready to experience the sights and tastes of beautiful Florence. Our concierge pointed us to the Museo HZero train museum. Florence is a small city and can be walked across in 20 minutes.
First lunch at Il Profeta, a 10 minute walk from the hotel…famous for John Travolta pasta. I ordered it. It was over $40. It was not worth it. It tasted like cream of tomato soup on top of fat tube pasta noodles. But do go, because the wait staff is so accommodating a kid friendly. No website. Just Google.
The HZero Museum was nearby so we stopped in and were WOWED. The girls didn’t want to leave. It’s one giant train set with all the details, modeled after a German city. www.hzero.com I never would have sought this out had our hotel concierge not recommended it!
We grabbed some gelato and walked to the Piazza del Duomo, the Piazza Signoria and walked along the River Arno back to our hotel to swim.
We had one of the best dinners of our trip at Trattoria ZaZa that night. Another restaurant where reservations are essential. Family-friendly and reasonably -priced, we sat outside and ate our fill of pasta dishes, again! www.trattoriazaza.it THEN, we went to the Mercato Centrale across the piazza for dessert. This is also a good inexpensive option for Italian food hall style dining for families. www.mercatocentrale.it
Day Two
We went to the Uffizi Gallery for a semi-private tour. The Uffizi is the largest gallery in Florence and known for Bottecelli’s Birth of Venus. The tour was supposed to be kid-friendly, but our guide described each stop in such detail that the girls lost interest early on. When we were finally released from the 3 hour tour, they spent the remainder of our time at the museum pointing out paintings with naked people. Good times. www.uffizi.it
We crossed the crowded famous Ponte Vecchio bridge on our 15 minute walk to a pizza and gelato making class with Eating Europe in Oltrarno. Another great experience with this group!
Our last dinner in Florence was at La Giostra, where I’d first had a meal with friends in 2010. Lovely, fancy and totally worth the expense. We were the only family with kids, but the girls were very well behaved. www.ristorantelagiostra.com
Other points of interest we didn’t explore this time…
Academy: where Michaelangelo’s David sculpture resides. After the Uffizi experience, a naked David was taken off the itinerary.
Piazza de Michaelangelo: 10-15 minute drive outside Florence. The view is breathtaking over Florence.
Santa Croce: Renaissance tombs are featured here – Michaelangelo, Dante, Galileo and others. Go to the back of the church and to the right to find a monastery where monks make and sell leather.
Day Three
We were supposed to leave from Florence – Munich – Denver – Los Angeles. But instead…
MUNICH, GERMANY
Less than 24 hours
Our flight arrived late into Munich and while we had time to make the connection, an egregious Passport Control line and a lack of security guards working the final security check before the gate meant we got to spend an extra night in Europe.
Instead of going to the long United Customer Service line, we went to the Lufthansa lounge and rebooked with a concierge there. He apologized and promised a free hotel and meal…both of which were available at the Best Western Munich Airport Hotel. Since it was only 5PM and we had our carry on bags with us, we opted to forgo “free,” take an Uber into the city center of Munich and pay to stay at a Marriott hotel near Marienplatz.
The girls barely remember their last Munich trip until we started walking to Marienplatz. Memories flooded back and they were excited to be back. We found a German bar with outdoor seating and flatscreen TVs set up to watch the EuroCup semi-final of Netherlands vs England. SO MUCH FUN. Beers and brats and cheering Germans!
We walked to Marienplatz afterwards then took a cab back to the hotel.
One day later than expected, we had an uneventful flight direct from Munich to Los Angeles on Lufthansa with two girls who I begged to stay up when we landed at 3PM…and who promptly fell asleep in the Uber on the way home. I tried!
It was the perfect trip to Italy and the perfect amount of time. We loved the trip, but were ready to be back home.
We Don’t Sit Still 
Love every word! Next time I’m traveling with you guys! xoxo
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