Dear Traveller friends,

after exploring some of the most beautiful places in the region, it’s time to plan an extensive tour to discover Tuscany.

Since there are many destinations you absolutely don’t want to miss, you’ll need at least a couple of weeks to get to know Tuscany — from 12 to 16 days.

What to expect

“What should I expect to find in Tuscany?”

If this is the question you’re wondering about, the answer is simple. Everything!

This region, in fact, is full of wonders. You’ll find towns steeped in history and traditions, beautiful landscapes, ancient medieval hamlets and excellent typical cuisine.

How to arrive

The tour I’m going to recommend is a circuit. This way, arriving by car, you can start from the most congenial point. If you arrive by train or plane, then you can follow the tour as I present it to you.

If you don’t want to or you can’t reach Tuscany with your car, your main reference point is going to be Florence. Here, in fact, there are the most important railway station and airport in the entire region.

Florence’s railway station is called Santa Maria Novella, and it’s in the city centre. You can easily reach it with high-speed trains. With a 90 minutes ride, you can arrive in Florence both from Rome and Milan.

If you prefer the plane, you can land at Amerigo Vespucci airport, situated in the northern part of town. As an alternative, you can consider the Galilei Airport in Pisa. Both airports are served by many companies that run flights to Italy from the most important European cities.

Once you reach Florence, you can visit the town with public transportation or on foot. However, for the rest of the tour, you’ll need to rent a car. Most of the places we’re going to visit, in fact, aren’t served by public transport.

When to go

The climate of the towns and villages in Tuscany is typically continental and thus not particularly favourable for tourism. Summer days, especially in big cities, are often wet and scorching. During winter, instead, the weather can be freezing. That’s why the best times are spring and autumn.

The Tour

Now we come to the juicy part: planning the tour! Here are two itineraries, the shorter one (12 days) and the extended one (16 days). Here I’m just going to list the stops. If you want more information on single destinations, just click on the links!

Tour Toscana breve
Tour Toscana breve
Tour Toscana esteso
Tour Toscana esteso

Day 1

You can devote your first day to the visit of Certaldo Alta and San Gimignano. Supposing you arrive in Florence by mid-morning or late morning, you’ll have plenty of time to get your rented car and head towards these two gorgeous hamlets. They are more or less 60 km far from Florence.

San Gimignano dalla Torre Grossa – Photo Credit: Andrea Gigliotti

Day 2

Your second day can be dedicated to the Chianti region down to Monteriggioni, a beautiful medieval stronghold totally surrounded by ramparts. Along the road, you’ll be able to discover many fascinating hamlets and villages and some of the most famous vineyard landscapes in Italy.

Monteriggioni - Photo Credit: Andrea Gigliotti
Monteriggioni – Photo Credit: Andrea Gigliotti

Days 3 and 4

The third and fourth days are the ideal time to visit the Orcia Valley, one of the most famous and envied wine-growing region in the world. You can spend the first night in Montepulciano, while during day 4 you should go back and reach Siena.

Panorama tra San Quirico e Torenieri - Photo Credit: Andrea Gigliotti
Panorama tra San Quirico e Torenieri – Photo Credit: Andrea Gigliotti


If you can add one day to your tour, at this point, you can visit Arezzo, a beautiful town rich in history. Even if it’s not among the most famous destinations, Arezzo is worth a visit if you have time on your side.

If you decide to make this extra stop, you can adjust the itinerary this way:

– day 4: devote it to the visit of Buonconvento, Montalcino, Castelnuovo dell’Abate, Castiglione, Bagno Vignoni and San Quirico (all included in the Orcia Valley). Get to Pienza and spend the night in town.

– day 5: visit the beautiful Pienza and then move on to Montefioralle, Montepulciano and, finally, Arezzo.

– day 6: spend the day visiting Arezzo, then reach Siena in the late afternoon.

Day 5

If you are going through with the shorter tour, your fifth day will be devoted to Siena, one of the most fascinating towns in Italy.

Palazzo Pubblico - Photo Credit: Andrea Gigliotti
Palazzo Pubblico – Photo Credit: Andrea Gigliotti


Visiting Siena in one day is possible, but it will force you to skip some points of interest. If you want to enjoy Siena fully, plan to spend one more day here.

Day 6

On the sixth day of your tour, leave Siena behind you and reach Pisa. During the journey, however, you can’t miss a stop at Volterra. Despite this stop, you’ll have plenty of time to visit Pisa in the afternoon.

Piazza del Campo – Photo Credit: Andrea Gigliotti


If you have time, after visiting Pisa, you can spend two days visiting Elba Island. On this island, which is part of the Parco Naturale dell’Arcipelago Toscano, you’ll find beautiful shores and unspoilt nature. In such a demanding tour, a couple of relaxing days aren’t a bad idea, after all. You can spend the first night of your extra days on the island and come back to Livorno the following afternoon.

Day 7

On your seventh day leave Pisa (or Livorno if you are doing the extended tour) and reach Carrara to visit the famous marble quarries. After seeing so many marble statues and buildings, now it’s time to discover where the marble comes from. Besides the cultural aspect, the landscape is suggestive and unique, with its white mountains and the sea on the background. After spending your lunchtime in Colonnata, eating a sandwich with the renowned lard, it’s time to get back to your car and reach Lucca.

Ponti di Vara - Photo Credit: Andrea Gigliotti
Ponti di Vara – Photo Credit: Andrea Gigliotti

Day 8

After spending the previous afternoon in Lucca, you’ll be able to use the morning of your eighth day to complete the visit around town. After touring Lucca, it’s finally time to head towards the final destination of your tour: Florence. If you don’t want to miss any of the beauties of Tuscany, before arriving in Florence, you can devote a couple of hours to Pistoia.

Days 9,10, 11 and 12

Your last four days are devoted to Florence, capital of the region. This town is so rich and beautiful that it’s worth the travel alone. However, at the end of such a tour, it’s going to be the proverbial icing on the cake. You’ll be left open-mouthed.

Cattedrale di Santa Maria del Fiore – Photo Credit: Andrea Gigliotti

For the present, this is all for what concerns destinations in Tuscany. However, I hope to see you soon for other wonderful Italian destinations.