Exploring Tuscany

As first time travelers to Tuscany, we quickly found out when planning our trip that Tuscany is quite a big region with many cities and that there are many “trail” options to choose. Where to start and end and everything in between. It felt a bit daunting at first, but after some research – we found our trail. So planning is important, especially if wanting to visit many cities/towns. We had 8 full days to spend in Tuscany and wanted to experience as much as possible – without making it exhaustive.

We have wanted to see the leaning tower of Pisa, so we started there, had an overnight stay and took the train to Florence and from there continued to a small town called Impruneta (30min from Florence) at the stunning Residenza ill Colle . This was our base for some days. Highly recommended hotel.

Residenza il Colle garden
Residenza il Colle garden


Getting around

For us there was no doubt how we wanted to get around – renting a car. I am sure there are other options like the bus, but driving is really the best option. It’s practical and gives you freedom to go wherever and whenever. Exploring essentially becomes more effective and pleasant. We rented and delivered in Florence.

On the road
On the road

Where we went

The better planning before the trip, the easier it will be. Once you have done your homework it is all about living out your plan. The towns (after Pisa and Florence) that we chose to visit were Montepulciano, Montalcino, Siena and San Gimigiano. We had put in some flexibility to see other smaller towns in between, but these four were the main trail. Montepulciano and Siena were daytrips. San Gimigiano was an overnight stay. Montalcino (Si Hotel) was our base for some days.

San Gimigiano


The food in Tuscany is not complicated, it is simple, fresh and delicious. In the towns with heavy tourism like San Gimigiano and Siena it can be difficult to find quality meals past many tourist traps. Again, research is key. We really hate getting rubbish food for our money, so we make sure to put in some time in finding good places to eat and make bookings in advance. Bear in mind that most restaurants are closed from 14.00 in the afternoon and open again from 19.00/19.30. Some as late as 20.00.  Must try is Picci with wild boar and Tuscan steak.


Shopping (apart from wine) was not on our agenda, but we saw that there were some decent stores in Montalcino and Montepulciano. Siena is a bigger city, so you will find stores typically found in big cities, well known high street and luxury brands and everything in between.

Must do’s

Our check list for Must do’s in Tuscany that will make your trip even more pleasant and in some cases save you some worries.

  • Eat at least one gelato
  • Rent a car with good insurance
  • Visit vineyards/wineries for wine tasting and tour
  • Drive through Val d’orcia and see the picturesque landscapes
  • Bring a good camera
  • Book hotel with a pool

Enjoy your Tuscany trip planning.

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