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Where?

Italy (Milan, Rome and Montepulciano)

The ancient city of Rome is center to Italy’s historical influence and home to landmarks such as the Forum, the Colosseum and the Vatican City. Between Rome and Florence you’ll find the stunning little hilltop village of Montepulciano, which sits in the heart of Tuscany’s wine country.

Rtip: Anytime you are traveling abroad we suggest securing travel insurance. Contact us directly for information on the best options.

When is the best time of year to travel to Italy?

If you want comfortable temperatures and to avoid intense crowds, visit between April and June (with the exception of Easter), or mid-September to October. We went over Spring Break in March and the weather was outstanding, sunny and in the mid-70’s. Although we experienced some American “spring break” crowds in the bigger cities (particularly Florence), they were pretty manageable.

How do we get there?

Our ‘cheap tickets’ had us flying in and out of Milan. We found the deal on Flight Hub and booked together as a group of eight.

How should we get around?

We arrived early morning in Milan and took a Eurostar train to the Milano Centrale train station. From there we bought tickets for the train to Rome. We did not pre-book our tickets in case of flight delays. Trains depart for Rome every hour, so they are easy to catch, although the express train runs a little less frequently. While the express train is only three hours, the slower train allows you to take your time and enjoy the view. Once we arrived to the Termini train station in Rome, we took a cab(s) to our apartment near Piazza Navona.

We decided not to rent a car during our stay in Rome. We mostly walked or easily grabbed an Uber or hailed a taxi when necessary. On our last morning however, we rented a nine passenger van from the Europcar rental desk at the Termini train station. From there we drove to Tuscany and drove the van for the rest of our trip. Husbands, Erik and Marty navigated, while Kim and I did our best to keep the kids in line in the back of the van.

“The van’s name was ‘Vito’. Every morning when we would get to the van for our adventure, the whole group would say in our best Italian accent, “Ciao Vito!!!”

Where should we stay?

In Rome, we stayed for three nights in a charming apartment just one block off Piazza Navona. It was in a great central location where you could easily catch a cab. We found the apartment through Plum Guide, and if you haven’t used Plum Guide before, you should, we have always been pleased with our experience. The Rome apartment was ideal for two families, had a large area for hanging out, four bedrooms and a kitchen. The only thing I wish the apartment had was a rooftop patio, that would have been amazing.

In Tuscany, we spent four nights at a airbnb in Montepulciano. The home was comfortable and centrally located in the historic part of the city. The only downside was its multi-levels, so lots of stairs, but overall it was charming and worked well for our group.

Rtip: If you are looking for a boutique hotel property, the six suites at Fattoria San Martino has it all; panoramic views of Montepulciano, organic gardens and orchards as well as a natural swimming pool.

In Milan, we stayed only one night at family-run hotel, Osteria Della Pista, near the airport. We had an early flight home the following morning so that was perfect.

What should we do?

I think when you are traveling with young kids, it’s important to let go of the expectation that you are going to see everything. Have a few key places in mind you want to visit, but also leave time to just enjoy the day. One of my favorite memories was watching the kids play Uno with a little Italian girl in the piazza while the adults sipped coffee and cocktails. Being on a relaxed schedule allowed for these kinds of moments happen.

In Rome,

Day 1

We arrived late afternoon and enjoyed dinner at a neighborhood restaurant just around the corner from our apartment. We went to bed early so we were on a good schedule for the next day. 

Rtip: A great neighborhood ristorante recommendation from Roam Guide insiders is Matricianella near the river the Spanish steps and the Trevi fountain.

Day 2

After a full day of sitting in planes, trains and automobiles we tried to focus on seeing everything we could outside on day two. That way the kids could move around and the fresh air could help us all adjust to the time change. We opted out of museum tours like the Vatican and instead walked all over the city. It’s surprisingly easy to cover a lot of ground in Rome, and we were lucky enough to have fantastic weather. We made our way to see the Pantheon and the Spanish Steps, visited a strange and quirky bone church, and ate gelato at the Trevi Fountain. Erik and I also hopped into a cab with our kids and took them to visit the school where we met 20 years prior. It was lovely to reminisce while we toured the grounds.

“We ate gelato every day. Sometimes twice a day. If there’s a line out the door that’s a pretty good indicator it’s going to be delicious.”

Day 3  

We walked to Castel Sant'Angelo, a fortress near the Vatican which the kids thought was cool. We visited St. Peter's Square before taking a cab to the Colosseum and the Roman Forum. We pre-booked a private tour with a guide through Walks Inside Rome. This was a big hit with our entire group and the guide was great with kids. I recommend you get the headphones. The earpiece experience lets you hear what the guide is saying while still observing the art, and without having to intently listen or lean into the guide. I also think it's important to choose a small group tour, less than 15 people, or look for private. This allows for flexibility, especially with kids, who are bound to need a few breaks.

Rtip: if you decide to make time for the Vatican it’s essential to have pre-booked access to avoid the lines. We suggest you consider Walks of Italy and their early entrance small group Vatican Tour.

After the tour, the kids were pretty wiped out, so the dads took them back to the apartment while Kim and I went to the Prato neighborhood for a little shopping and a glass of wine.

“In Prato, we found a darling shop called Kokoro, with handmade dresses in lovely patterns and fabrics. I got a red pleated skirt that gets so many compliments. It’s always fun to say, ‘I got it from a little shop in Rome!’”

On our last night in Rome, we took cabs to the Trastevere neighborhood where we walked around a charming square and ate at a wonderful restaurant called Mama Eat. Since Kim and I are both gluten-free, this restaurant was perfect for us, but also a highlight for the rest of the group.

Day 4

Before we packed up and left town, Kim and I walked to the Campo di Fiori market for coffee at the farmers market. I picked up some spice packets, jars of pesto, and sun-dried tomatoes. Afterwards, we loaded up our families and headed to the Termini train station where we grabbed our van (“Ciao Vito!”). It’s only a 2.5 hour drive to Montepulciano where we stayed for the next four nights. Along our journey we stopped in a small town called Magliano Sabina for lunch. It was charming, quiet and gave us an authentic sense of the Italian countryside. After lunch, the kids found a park and we enjoyed some gelato (surprise!). On our arrival in Montepulciano that evening, we settled into our apartment and found a local restaurant for dinner.

In and around Montepulciano,

Day 5

Prior to our trip Kim arranged for us to spend a day at Terre Di Nano, a villa surrounded by olive groves and vineyards just outside of town. We took a cooking class from Chef Georgio where we learned how to make gnocchi, tiramisu, and saltimbocca. The cooking class was a fantastic, hands-on activity to do with the kids, and a great experience for the adults as well. We shipped wine back to the states and they gave us olive oil to take home as a gift.

After preparing all the dishes, we sat on a long table outside so we could sample what we made in class. They would bring us a dish, and then we’d go walk around the grounds only to come back for the next course. The kids roamed free on the property, through the vineyards alongside goats, chickens and friendly old dogs. The whole day was idyllic. 

On our way back to Montepulciano, we stopped in the town of Bagno Vignoni, which has a natural hot springs. We paid for day passes and swim caps before happily floating in the springs attached to the Post Marcucci Hotel.

“We felt like we were in a Fellini film, floating in the hot springs surrounded by old Italians in bathing caps at sunset.”

Upon our return to Montepulciano we had dinner at La Bottega del Nobile near our apartment, and then hit the hay. If I am being honest, the restaurant was not great for a large group with children. However, it would be a great choice for a date night.

Day 6  

Today we drove to Florence for a day trip. We parked ‘Vito’ in a ramp near the city center — which we learned the hard way is a very expensive thing to do. If we had planned better, we might have parked smarter or taken a bus to the city center.

We walked across the Ponte Vecchio to Palazzo Vecchio and on to the Piazza Duomo. We ate lunch at a cafe near the Duomo before heading to the Accademia Museum for our scheduled tour of The David. Once again we had great weather, so other than the museum tour which took about an hour, we spent most of the day wandering outside. We stopped at the San Lorenzo Market where we got all four kids matching Italian soccer team sweatshirts. In hindsight, we should have done this sooner, as it was much easier to spot them in a crowd. 

“I also found great leather goods in Florence. Shhh, don’t tell Erik, I came home with three new purses!”

Florence was very touristy and it got considerably more crowded as the day went on. We didn’t want to drive back at night so we headed to Montepulciano late afternoon instead. It was there we found a charming family restaurant called Ristorante Godimento Divino to end our evening. The kids were thrilled with their pasta choices and the adults were quite happy with a delicious Tuscan steak and some local red wine.

Day 7

For our last day in Montepulciano, we gave “Vito a resta” and decided to just meander on foot. It’s a very hilly town, so we definitely got our exercise. We visited the local shops and the kids played soccer in the piazza with the local kids. It was low key, relaxing and quite perfect. 

That night we had the most amazing steak dinner at Acquachetta, right around the corner from our apartment. This place was highly recommended by many sources and it was incredible! It had been closed for the season but opened the day before we left. We were lucky enough to get in and it was the meal of a lifetime. Florentine steak, mouth-watering mushrooms and superb wine. To end the day, we enjoyed a spectacular sunset from a terrace near our apartment.

Rtip: There are actually quite a few wineries that sit inside the town of Montepulciano. If you have to pick one for a visit, the charming and family-run, Azienda Agricola Ercolani also sells local delights, like pecorino and tapenade. They offer free wine tastings, which lends well to tourists, but the wine is fantastic and the shop has unique access to explore the underground city which connects seven historic buildings to their cellar.

Day 8

We started the day with breakfast at the historic Cafe Poliziano, before packing up and hitting the road back to Milan. Let me tell you, Cafe Poliziano has an incredible view and the best cappuccino. On the drive, we stopped in Modena for lunch and had a tour of the Ferrari Museum. The gluten-free tortellini at the museum cafe was pretty incredible. Although the museum was fairly compact, it was full of shiny, fancy cars, which was fun to see. That night we stayed in for a low-key dinner at our hotel before our flight home the next day.

What is the one can’t miss item on your itinerary?

The farm visit and cooking class to Terre Di Nano was epic. Highly recommend.

Tell us something we don’t know?

Kim and I are both gluten free and we were amazed at how accommodating the Italian restaurants are. Almost everywhere there are gluten-free pizza and pasta options and they are happy to walk you through the menu to determine what you can and cannot eat.

Would you change anything?

Even though we flew in and out of Milan, we didn’t spend any time in the Alps (and they are so close!). We would all love to go back and see the Alps or the Amalfi Coast. This trip was huge for us just in realizing we can do this with kids! We only scratched the surface in 8 days, but it was a positive experience and we are encouraged to go back.  

What should we bring with us?

Kim and I both love our Allbirds for travel that requires a lot of walking. They are crazy comfortable but still stylish. I could wear them all day and still have happy feet. Also, my Peak Design backpack is great for all kinds of reasons. You can tell the designers have traveled extensively, because they’ve thought of everything when it comes to adaptable ways to organize and pack for easy access. For day trips, I left my backpack at the apartment and took my Baggallini Crossbody Bag. It was perfect for holding essentials like credit cards, Euros, lip gloss, and my iPhone. I also always pack jewelry that is looks great with everything, day or night. Kim and I both have several pieces from Goldfine, a local MN designer that we love. A black leather Moto-jacket, like the one below from Madewell, is a key piece that can work well for day and night, especially for those “bumper seasons” when it can be a bit cooler. Finally, my 20 year old Italian speaking skills were rusty, but with the help of Google Translate on my phone, I could look up key phrases for conversation and directions.

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