Travelling as a single parent family is an adventure in itself. When you add the rolling hills, medieval towns, and carbohydrate-heavy menus of Italy into the mix, it becomes the trip of a lifetime. For years I had dreamed of taking my kids to Tuscany. I wanted them to see the cypress-lined driveways, taste gelato, and run freely through open fields that look like a Renaissance master painted them.
However, the logistics of managing a road trip with children on my own used to make me nervous. The idea of driving on roads, setting up child seats, and packing and unpacking our things every few days as a solo parent felt like a huge challenge. With some careful planning, a slow schedule, and the right car, our trip through Tuscany became one of the most enjoyable single parent holidays we have ever had. Here is how we did it, beginning in the place where the Renaissance started before moving to the countryside.
Starting in the Heart of the Renaissance: Florence
Our journey began in Florence. If there is one piece of advice, I can give any parent visiting this city, it is this: Do not attempt to drive here. The historical centre is a maze of pedestrian zones and strict ZTLs (Limited Traffic Zones). If you cross into them without permission, you could end up paying fines which isn’t worth the stress. It is far easier to just leave the car behind and explore on foot or by public transport. That way you can enjoy the city like a local without worrying about where you can and cannot go.
We spent a few days walking around Florence and were amazed by the size and beauty of the famous Duomo, the Cathedral of Santa Maria del Fiore. We ate more pizza than we should have, and the kids played in the Boboli Gardens until they were tired out. At times, Florence felt like is an open-air museum, but the whirlwind of noise and energy reminds you that the city is very much alive. Three days are the ideal time to explore the Museo Galileo, see Michaelangelo’s David, ride a vintage carousel, visit the Leonardo Interactive Museum, and catch sunset views. After all that local art and culture, we were ready to slow down in the countryside. That meant it was time to pick up our car and hit the open road.
Sorting the Wheels
As a single parent, I do not have another adult to wrangle the kids while I stand at a rental desk haggling over prices or figuring out car seat requirements. I needed everything sorted long before our plane even touched down in Italy.
To plan the transport for this leg of our journey I needed to find reliable car hire in Florence. Our vehicle had to have booster seats and plenty of boot space for our suitcases. I was also looking for comprehensive cover for absolute peace of mind because, when you are driving through narrow medieval streets, the last thing you want to worry about is a scraped bumper. Beware of companies that charge hidden fees, which can ruin your holiday budget.
Another important tip for anyone renting a car immediately after landing: Make sure your arrival time is not listed as your car pick-up time. Delays at baggage claim or passport control happen often. When arrival time and pick-up time don’t match, it is one of the most common causes of rental problems. Also remember that a credit card is required for rentals.
Kid-Friendly Stops in Tuscany
I had our bags packed in the boot and the kids strapped in as we headed south. The moment we left the outskirts of Florence the landscape turned into the Tuscan vistas that you see in the movies.
Siena: Gothic Architecture and James Bond
The next stop on our family road trip through Tuscany was Siena. There are several car parks outside the city walls and the walk to Piazza del Campo takes only around 10 to 15 minutes wherever you park. Once at the piazza, the children can run around safely while you enjoy an espresso at a café on the edge and marvel at the medieval architecture. Next admire the 13th century Palazzo Pubblico and the Fonte Gaia, the Fountain of the World, together. Don’t forget to tell the kids that Quantum of Solace, the famous 2008 James Bond film, was partly filmed here. There are plenty of other walkable sights in the pedestrianised city centre, such as the Duomo di Siena and I found the distance manageable even for young children.
Val d’Orcia: Wild countryside and Working Farms
Next, and possibly my favourite part of the trip, was a visit of the Val d’Orcia. This UNESCO World Heritage designated region is the beautiful Tuscany that we have all dreamt up in our minds. We stopped at working farms, so called Agriturismos, that invite visitors to eat, drink, and learn about farm life. The kids loved to run around the olive groves, meet the animals, pick ripe figs straight from the trees, and taste pecorino cheese made right there. These visits felt far away from the strict schedule of museums and city tours.
San Gimignano: Dramatic Skyline and Gelato
We also spent an afternoon in San Gimignano, which is famously known as “Medieval Manhattan” due to its skyline. Between the 11th and 13th century wealthy families built 72 tower houses here, of which 14 survived. You are allowed to climb the tallest tower, which has just over 200 steps and were rewarded with a 360 degree panoramic view of the orange-red tiled rooftops, the medieval piazzas, and the surrounding countryside dotted with olive groves and vineyards. Afterwards we enjoyed, what locals call the world’s best gelato, in Gelateria Dondoli in the Piazza della Cisterna.
Driving in rural Italy is a beautiful experience but doing it solo with kids requires a specific mindset. The key to our success was keeping the itinerary remarkably relaxed:
- Watch your journey times. The roads winding through the Tuscan hills are scenic but slow. A distance that looks like 30 minutes on a map can easily take an hour when you account for winding paths, tractors, and mandatory photo stops. I capped our driving at two hours a day.
- Plan the parking. In almost every Tuscan hill town, like Montepulciano or Pienza, non-residents are not allowed to drive inside the historical centres.
- Bring entertainment. Even with the most beautiful scenery in the world outside the window, kids will eventually get bored. Make sure to have travel toys on hand, whether that’s an iPad loaded with movies, a great family audiobook, or a card game that works on the road.
Taking a family road trip through Tuscany as a single parent is entirely achievable. With the freedom of your own vehicle, you can skip the crowded bus tours, set your own pace, and create memories in the quiet, sun-drenched corners of the Italian countryside.
