Best time to go: the best time to go is either in spring (April and May) or late summer to early Autumn (September and October). The landscapes are beautiful at this time of year and the temperatures are mild so it's perfect for tourism and sightseeing.
General advice: obviously as this is a road trip you need a car! The best way is to fly into Florence or Pisa airport and start the trip from there. In this itinerary we avoided Florence and Pisa city centres and focused more on the small Tuscany towns, but if you want to do a full week trip you can include them. The trip is slightly shorter if you start and finish in Florence.
The itinerary that we followed was:
Day 1: landing in Florence, San Gimignano and Volterra
Day 2: Monteriggioni and Siena
Day 3: Montalcino and Pienza
Day 4: Montelpuciano and Cortona, Florence airport.
Day 1: San Gimignano and Volterra
The towns in general are quite small and unless you are doing a stop for food it shouldn't take you more than one hour or an hour and half to see the entire town. Another thing to note is that most of the towns have parking outside the towns and for us it was very easy to park as we went in April and it was quite quiet.
First stop was San Gimignano, which is 55 min drive from the airport. San Gimignano is famous for its skyline of medieval towers. This is the most touristic town as it is quite close to Florence and there are regular buses taking you from Florence to the town therefore it's a bit more full of tourists compared to the other towns.
In San Gimignano you cannot miss: Duomo, Palazzo Comunale and Piazza della Cisterna. You should also pop by Gelateria Dondoli to try one of their amazing ice creams. As with all these towns, the main thing to do is to walk around and get lost around the narrow steep streets.
After that we went to Volterra, unfortunately it was super foggy, and we couldn't see much but for sure on a sunny day it's a very cute place. If you are lucky and it is a sunny day, make sure that you visit: Roman Theatre, Via Giacomo Matteotti, Piazza dei Priori, Duomo di Volterra and Piazza Martiri della Liberta from where you can enjoy a great view of Volterra.
Regarding where to spend the night I would recommend either "Castello di Fonterutoli" or "Fattoria San Donato", both are agrotourism type hotels. In both cases, you can also enjoy the property and have a wander around the vineyard as well as try their wines.
Day 2: Monteriggioni and Siena
The next morning, we went to Monteriggioni, which is 35 min drive from "Fattoria San Donato" and just 20 min from "Castello di Fonterutoli".
Monteriggioni is the smallest town of the ones selected for this road trip but it is super cute as it still has the whole fortification around the town almost intact. You can walk the whole town just in 1 hour or even less!.
From there it's time to make your way to Siena, which is just 25 min from Moteriggioni. In Siena make sure that you book a hotel with parking but that's relatively central so you can go to the hotel to park the car and start exploring this amazing town. In Siena, we stayed at "Villa Del Sole" and it was great! The location was fantastic and as this is a boutique hotel, it was very cosy.
Siena is just beautiful and, in my opinion, the prettiest town of Italy (and I have been in many...). So, what to do in Siena, first start by visiting Piazza del Campo where you will find the Palazzo Pubblico and its Torre del Mangia, as well as various palazzi signorili surrounding the piazza.
From there go to the Duomo di Siena and choose one of the 3 options of passes that the duomo offers, each pass offers different options. You can visit the inside of the Duomo, the library, the museum and the panorama (views from the top of the museum), crypt and baptistry. Just take into account that there are loads of stairs to get to the panorama and the stairs are very small so you can get a bit dizzy as it is a spiral staircase. It takes around 2 hours to visit the main bits but if you want to see all the spaces it can take longer.
I recommend going for lunch to "Pretto Prosciutteria" so you can try Italian cheeses and cured meats. The place is small and informal but very tasty.
After lunch you can visit the Piazza Salimbeni, which is notable for still housing the offices of one of the first banking houses in Europe, the Banca Monte dei Paschi di Siena. At end the day, make your way to the vista panoramica di Siena to enjoy beautiful views of the city from a different perspective.
For dinner go to "La Taverna di San Giuseppe", it is a very popular place, so it is recommended to book at least one week in advance. They serve Tuscan dishes and they specialise in dishes which include truffle. They have also a great selection of wines and the service is great. The food was delicious and I highly recommend it!
Day 3: Montalcino and Pienza
On day 3 go to Montalcino, which is a 50 min drive from Siena. The area is famous for its' wines, and the landscapes on the way there are incredible.
The most famous thing to do in Montalcino is to taste some wines from the region and explore the wine shops. You can also visit the Cathedral of the Holy Savior and the Palazzo dei Priori.
From there you can go to Pienza that takes 25 min drive. Pienza in my view, is the most beautiful of all the small towns that we visited (excluding Siena of course). It is charming and full of flowers and beautiful boutique shops. We also had lunch at "Trattoria da Fiorella" and it was really good, both the pasta dishes and the starters. In Pienza you can visit: Palazzo Piccolomini, Corso il Rossellin, Piazza Pio II and Via del Casello for a great view.
We spent the night at "Borgo Sant'Ambrogio", a beautiful hotel nearby Pienza with lovely surroundings and a very nice restaurant. The farm where the hotel is located is stunning.
Day 4: Montelpuciano and Cortona
For our final day we went first to Montepulciano, which is just a 20 min drive from Pienza, again like Montalcino this is a very famous area for their wines. What I liked the most about Montepulciano was the number of nice shops. Whilst there, you can also visit Piazza Grande, Comune di Montepulciano, Cathedral Saint Mary of the Assumption and the Fortezza Medicea.
And to finish, our last town to visit was Cortona, which is 35 min from Montepulciano. In Cortona we had lunch at "Preludio Restaurant" and it was another great experience. The service was excellent and we had a super nice lunch. In Cortona you can visit: Comune di Cortona, Piazza della Republica, Piazza Luca Signorelli and Chiesa di San Francesco.
From there we went directly to the airport that was a 1 hour 25 min drive from Cortona.
If I have to choose...
I think that it is important to mention how I chose to visit these 8 places. Basically, I knew that we didn't have much time so I took the selection of the prettiest towns in Tuscany from famous travel magazines and compared them against various travel bloggers suggestions. The names that were repeated the most times and that made sense in terms of being next to another town that I wanted to see are the ones that I chose. For example, I excluded Lucca as it was out of the way from the route that we wanted to follow, but I read that is an amazing place to visit and hopefully I can go one day.
I have for sure missed many other beautiful towns so ideas for future trips are welcome! After seeing all of this, if I had to choose my favourite towns/ places to visit it would be the following:
1. Siena
2. Pienza
3. San Gimignano
4. Monteriggioni
5. Montelpuciano
