Road Trip in Italy: Two Weeks Through Tuscany to Rome

Planning an Italy Road Trip After the Pandemic

Where do you go when you’ve spent three years unable to leave Singapore due to the pandemic? Italy, obviously.

After years without green hills, fresh Italian produce, and good wine, we were craving it hard. So when we finally could, we jumped on a plane (with very few plans) and headed to Florence. I travelled in by train with the kids, and my husband joined us by plane from the UK.

We had little to no plan, partly because we didn’t know where we were going until the last minute, but we did know one thing: we wanted a slow, flexible road trip through Italy, ending in Rome.

Starting Our Italy Road Trip in Florence

After arriving in Florence (already a firm favourite of ours pre-Singapore), we checked into a glamping site just outside the city for a couple of days. It was the perfect balance, time to relax, but also easy to hop into Florence whenever we wanted.

Florence felt like a gentle reintroduction to Italy: familiar, beautiful, and full of life. Wandering the streets, eating well, and easing ourselves into holiday mode.

How We Planned a Flexible Italy Road Trip

We took the trip in small chunks, planning just a few days at a time and using Booking.com to figure out our next move. We’d hired a car and knew we were flying out of Rome two weeks later, everything in between was intentionally loose.

This flexible approach ended up being one of the best decisions we made for our Italy road trip.

Siena: A Tuscan Stop with Movie History

Our next stop was Siena. I may have mentioned before that my husband has a thing for James Bond filming locations, and Siena was a good one, famously featured in the opening scenes of Quantum of Solace, during the Palio horse race.

We stayed in a beautiful apartment with (sadly) no air conditioning, but the views from the restaurant were so stunning they genuinely brought a tear to my eye. This was where we slowed right down, home-cooked meals, fresh local produce, local wines, and lots of rest.

A Tuscan Retreat Near Montepulciano

Next came a real treat, a place I’ve written about before. Mario’s place, A Tuscan Retreat Near Montepulciano, Terra Antica was the warm hug we didn’t know we needed. As I’ve mentioned before, we like to mix in a few luxury days on our trips. This was it for this holiday.

Comfy beds, hot showers, sun loungers, our own hot tub, and Aperols appearing as quickly as they could be made. Absolute bliss.

We were also close to Montepulciano, which completely captured our hearts. Mario pointed us towards local restaurants that were full of flavour and warmth, and far better value than some of the more crowded, well-trodden spots.

Ending Our Italy Road Trip in Rome

Our final stop was Rome. We dropped off the car and spent three full days walking, easily 20,000 steps a day, exploring every inch of the city.

We loved the Spanish Steps, the Forum, and the Colosseum, but my favourite moment was entirely unexpected. We reached the Chiesa dei Santi Luca e Martina Martiri and stumbled across a couple who had just got married. A surprise singing group appeared and performed [song] for them, it was pure magic, one of those travel moments you never forget.

Food Highlights on Our Italy Road Trip

We ate incredibly well in Rome too. It was fun to notice how pasta dishes changed as we travelled, Florence to Tuscany to Rome, each region putting its own spin on the classics.

My daughter especially loved the ragù in Rome, but honestly, the gelato was divine everywhere we went.

Final Thoughts on Doing a Road Trip in Italy

This Italy road trip gave us exactly what we needed: freedom, flexibility, incredible food, beautiful scenery, and the joy of discovering places without rushing.

Driving through Italy allowed us to travel slowly, change plans when we felt like it, and experience each place in its own time. Tuscany, Florence, Siena, Montepulciano and Rome all offered something different — and together they made for a trip we’ll always remember.

FAQs: Road Trips in Italy

Is Italy good for a road trip?
Yes, Italy is ideal for road trips, especially in regions like Tuscany where distances are short, roads are scenic, and small towns are easy to explore by car.

Do you need to plan an Italy road trip in advance?
Not necessarily. We planned only a few days at a time, which gave us flexibility and allowed us to follow our instincts. Having accommodation options and a rough end point helped.

Is driving in Italy difficult?
Driving in rural Italy and Tuscany is straightforward, though cities like Florence and Rome are better explored on foot. We found it easiest to park up the car outside city centers.

How long do you need for a road trip in Italy?
Two weeks was perfect for us, enough time to explore Tuscany slowly and finish with a few days in Rome without feeling rushed.