Over the Easter break, my sister and I finally made it happen: a 4-day Tuscany road trip through some of Italy’s most beautiful destinations. Our route took us from Bologna to Siena, through Montepulciano and the Val d’Orcia, and finally to Florence.

There were a few places we’d both wanted to visit for a while, so it felt like the perfect time. This Tuscany road trip was very spontaneous, we saved a few spots from social media, but most of the planning, including hotels, was done last minute.

She drove from Turin, I flew into Milan, and from there our Tuscany road trip officially began.

Bologna - Where Food and History Meet

Bologna had been on my list for a while, so stopping there made sense. Our hotel was just outside the city. After breakfast, we drove in and parked near Giardino della Montagnola, about 15 minutes from the centre. Quick tip: watch for ZTL zones. If they’re active, you can get fined.

We explored the city on foot. Bologna is full of history, with something on every corner. It’s also the birthplace of ragù alla bolognese. It’s known for tortellini, tagliatelle al ragù, lasagne, mortadella, and tigelle.

We walked under the famous portici. They make exploring the city pleasant, especially on a sunny day. It was quite busy, but the atmosphere was still enjoyable.

We stopped at the Two Towers, Asinelli and Garisenda. They’re iconic, slightly leaning, and very photogenic. Then we headed to Piazza Maggiore. Here you’ll find the Fountain of Neptune and the impressive Basilica di San Petronio. We didn’t go inside, but it’s worth it if you have time. We also visited the Salaborsa Library, which is a lovely quick stop.

By early afternoon, we were ready to leave. Siena was next, about a 3-hour drive.

Siena - Life in the Heart of Tuscany

We arrived in Siena just in time to check into our hotel near the old town. Cars aren’t allowed inside, so the location was perfect.

After a bit of rest, we headed out in the late afternoon towards Piazza del Campo, one of the most beautiful squares in Italy. Siena is famous for the Palio, a historic horse race held twice a year right in this square.

We took our time, enjoyed an aperitivo, and later had a lovely dinner at La Bottega di Sotto. Before dinner, we visited the Duomo, which is absolutely stunning. The black and white marble makes it really unique, easily one of the most impressive churches I’ve seen.

After dinner, we grabbed some gelato and ended the night with a few drinks and new friends. A long but perfect day.

Montepulciano & Val d’Orcia

The next morning, we headed to Montepulciano. If you’re a Twilight fan, you might recognise it from New Moon.

Like many Tuscan towns, cars aren’t allowed in the centre. We parked just outside and walked in. No plan, just wandering.

On the way up, we were invited to a tour at Ercolani Cellars. It included a visit to underground wine cellars and a free tasting. Four glasses, plus local food. The tour was surprisingly interesting and full of history. We even won a bottle of wine each during a short quiz.

After that, we kept walking until we reached the top. The views there are beautiful and peaceful.

Later, we stopped for lunch at a small restaurant with an amazing view, Romantico. Simple, local food, but a moment to remember.

On the way back to Siena, we drove through Val d’Orcia. Rolling green hills, wide views, and iconic cypress trees, a true symbol of Tuscany.

We stopped near Crete Senesi by Asciano. It honestly looked like a Windows wallpaper. We also passed Castello di Leonina, a great spot for views and a short walk.

Sunset in Siena

Back in Siena, we didn’t want to miss the sunset, so we headed to a panoramic viewpoint just outside the city. There’s a parking area and even a small bar/restaurant.

We brought takeaway and a bottle of prosecco and just sat there watching the sun go down. The light over the city was incredible, soft, golden, and almost surreal.

Simple moment, but probably one of the highlights of the trip.

Florence - A Return to Renaissance Beauty

The next day was all about Florence. We’d both been before, so we kept it relaxed.

We stopped briefly at a viewpoint on the way in, then parked just outside the centre to avoid the ZTL. First stop: the Duomo. No matter how many times you see it, it’s still breath-taking.

We wandered through the streets, then stopped for lunch, at Trattoria Dedo, this time for a proper bistecca alla Fiorentina, paired with a glass of Chianti.

After lunch, we visited Piazza della Signoria, with its statues and open-air museum feel. We stepped into Palazzo Vecchio for a quick visit, still just as impressive.

Then we headed to Ponte Vecchio. It was crowded, so we skipped crossing it and instead enjoyed the view from a distance.

A final gelato by the river, and then it was time to hit the road again.

The End of the Trip

Our last stop was Reggio Emilia, about two hours away. On the way, we caught another incredible sunset, one of those you don’t expect, but won’t forget.

We had dinner at Doppio Malto, with good food and local beer, the perfect way to end the trip.

The next morning, my sister dropped me at the airport, and we went our separate ways.

This trip was everything we hoped for and more. Beautiful places, great weather, amazing food, and just the right mix of planning and spontaneity.

We came back home with full hearts, and already thinking about the next one.