Road Trip Through Tuscany, Italy

Tuscany rolling hills chianti

The Italian region of Tuscany was high on the list of ideal destinations when we started planning our travels back in 2020. Photos and videos online of rolling hills, delicious wines and quaint old towns situated on hills captured our imagination. When planning Tuscany, we wanted to capture the some of the experience of the area, but could only spare a few days in total (due to Schengen zone calculations – a separate issue, more on that at a later date). If you are weighing up if adding Tuscany to your trip is worth it, then this post should be the confirmation you need! Tuscany was amazing, and definitely should be on your list! Read on to see the towns we visited!

Our Road Trip Through Tuscany

San Gimignano

San Gimignano is studded with stoned alleyways and medieval towers – some of which you can climb, boasting incredible views of the Tuscan landscape. If you’ve had you’re fill of climbing stairs there are plenty of other viewpoints from which to take in the surrounding valley and a market set up in the square to try the local delicacies. Friends who had been before also recommended we visit the ‘world famous’ Gelateria Dondoli. While we were sceptical about such a glowing recommendation, we did in fact enjoy some pretty incredible gelato flavours – blackberry with lavender, strawberry with rosemary, and cinnamon. The only downside to San Gimignano we felt was that it was already heaving with tourists by 10am. Best to go early in the morning or ideally outside of peak season if you can. For coffee with an incredible view of rolling Tuscany hills, check out Café Giardino at the entrance of the town.


This place felt like something out of a fairy tale with its medieval fortifications surrounded by olive trees and a quaint central square. This town is small in stature, but it was one of our favourite stops. If you’re travelling by car it makes for a great place to go for the afternoon after a morning spent exploring the more touristic town of San Gimignano.

Strada in Chianti

We really only stopped here for half an hour or so to get some food for a picnic. There was an authentic little deli selling smoked meats, cheese and wine as well as a market set up in the square. Everything else was closed as we visited on a Sunday (note: try to avoid visiting little Italian towns on a Sunday if you can, we’ve found its common for most places to be closed). Overall, this isn’t a stop you need to add to your road trips as other towns will likely deliver more vibes and things to do.

Greve in Chianti

This cute little town is located in the heart of the Chianti wine region. Whilst probably not worth going out of the way for, it’s not a bad stop for wine lovers. It could definitely worthy of a quick pit stop if you’re not on a strict schedule. Wander through the main square and stop at one of the local restaurants for lunch.  


While it was definitely the biggest of the towns we visited in Tuscany, it somehow still managed to maintain somewhat of a ‘small town feel’. Perhaps part of the charm for us was that we really didn’t know what to expect – this made walking around a corner to discover the ornate façade of the Lucca cathedral particularly impressive. There are also 9 ancient towers scattered around the city – the most famous of which being the Guinigi Tower since it was built with a small garden of oak trees at the very top. spent around 4 hours here, although you could very easily spend a whole day. Some of our favourite moments were enjoying a coffee in the city’s main square and strolling along the city’s tree lined city walls. The main square is unusual for Italy, the oval shape is based upon a former amphitheatre which lies a few metres below the surface. This creates a unique and beautiful setting for lunch, coffee, wine or some photos. Read more about our day trip to Lucca here!

Castello Vicchiomaggio

We absolutely loved our stay in Tuscany, and would encourage others to ‘get out of the big city’ and stay in the countryside when visiting this part of Italy. We stayed at Castello Vicchiomaggio ( info here), an old Tuscan tower and villa. This place boasted impressive views of the rolling hills, an infinity pool and was reasonably priced compared to similar levels of opulence back in Australia. For those interested in checking out more, take a look at our gallery and thoughts on Castello Vicchiomaggio here!


The famous town of Pisa was our last stop in the region before we headed out to the coast (Cinque Terre). We had heard mixed reviews from Pisa, and had low expectations for our visit. Overall, we didn’t rate the town that highly, however the main street had a good vibe and lots of restaurants. The tower itself is on more of an angle than we had expected, but overall doesn’t take up a lot of time after a few photos. The benefit of staying in Pisa for us was cheap accommodation, and to be close to the coast for our train to Cinque Terre.

Where we missed:

There were so many towns and places we wanted to visit in the Tuscany region, but due to time constraints, we couldn’t make it happen. We would definitely would add on Sienna, and the Saturnia Hot Springs. We also loved the little towns, and would enjoy a slower period of exploring the little towns over a few weeks.

Getting around Tuscany

When deciding the best mode of transport for you Tuscany adventures, you probably need to consider what you want to do and see. Keen to see some of the bigger towns on day trips? A train will probably suffice, and can get you to towns like Siena and Lucca. Keen to see a few towns in the one day? Perhaps a day tour from Florence to see towns like San Gimignano and others nearby. Costly, but good if short on time and okay with working on others schedule. The bus? Perhaps, but we had heard stories about the speed (it’s slow), how busy it gets, the heat in summer, and waiting around to get the bus back.

The best option? Hire a car! We hired a car from Florence, and then dropped it back in Pisa (as we headed out towards Cinque Terre). This allowed us to explore multiple towns, and on our own time schedule. This is especially important if you are looking to stay at a villa in Tuscany like we did (read further for more on our incredible stay!). The roads in Tuscany are some of the most beautiful we have ever driven, and are quite easy to navigate. The downside? Car hire is quite expensive and popular in peak times. We paid around $200 (AUD) per day for the hire (an automatic car, manual is cheaper), and insurance is even more if you get it.

Book a tour to Tuscany!

As mentioned above, getting around Tuscany can be a challenge, particularly if you don’t hire a car. Take a look at some tour options below which may make your trip simpler, easier and more fun!

Where to stay in Tuscany?

We would recommend Castello Vicchiomaggio (see above), however we have listed a few impressive options below that took our fancy. We haven’t stayed here but may look to in the future.

  • Relais Villa Grazianella is a breathtaking property nestled in the stunning Tuscan countryside. With a grand driveway and picturesque vistas, this villa offers an exceptional stay. Don’t miss the chance to experience the magic of Relais Villa Grazianella – explore more here!
  • Borgo Del Cabreo is located in the beautiful wine region of Greve in Chianti, making it the perfect base to explore neighbouring towns. It’s seriously stunning.. take a look here!

See some stunning Drone Footage from Tuscany


Have a look at what we did during our 48 hour stay in Florence, Italy. Check it out!

Take a look at some more highlights, tips and advice from our travels in Italy! Check it out here!

See some highlights and great tips from our time in Venice! Have a look here!

Check out further highlights from our time in the Europe! Take a look!

Keen to take a look at further travel memories and advice? Take a look here!

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