A Two-Week Itinerary for Tuscany

Have you taken two weeks off and decided that Tuscany is the place for your next dream holiday? Good for you! Tuscany is an amazing part of Italy and if you are going to all that way, you may as well spend as long as you can there.

Two weeks is a pretty good length of time to spend in Tuscany because let’s face it Tuscany is not just about Florence and Siena. There are so many little hilltop villages to explore, so much stunning countryside to drive through and so many nice wines to taste! Oh, and did I mention the food?


Keep reading for an awesome two-week itinerary for this incredible part of Italy.

El Duomo Firenze

Florence (2 days)

Florence is also home to the famous David statue by Michelangelo and it’s the city of Dante Alighieri. Last but not least, Florence contains one of the most awe-inspiring sights in Italy, its Duomo which is an absolute must visit! To easily wander around Florence by foot, try and find accommodation in its historic centre, close to all the main sights.

Although Tuscany is not just about Florence, a visit to Tuscany is not complete without seeing its most beautiful city. Florence is a city for anyone who loves art, history or architecture. It’s full of museums, amazing Renaissance-era buildings, stunning churches and a delightful river that splits the city in two.

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Tours in Florence

Beautiful countryside on near Greve in Chianti

Drive to Siena via Chianti and Road SR222 (1 day)

Renting a hire car which will make exploring Tuscany a whole lot easier. Pick up one and leave Florence in the early morning, heading down towards Siena where you can base yourself for a few nights.

Make sure you take the Via Chiantigiana road (SR 222), the most scenic route in Tuscany. The SR 222 winds its way through the Chianti area, showcasing its spectacular rolling green hills, field after field full of vines and beautiful little villages. The scenery is so stunning that you’ll make a lot of stops for photos.

On the way down, be sure to pop into some wineries to taste the local wines. We recommend Castello di Verrazzano near Greve in Chianti and Castello di Ama near Radda in Chianti. Both require advanced booking. You can book online via their websites.

Another great place to stop along the way (at least for the non designated driver!) is the Enoteca Falorni in Greve in Chianti. This enoteca offers more than 100 wines for tasting and a thousand wines for sale. It’s the perfect place to try Chianti wines and to stock up on some wine for the evening. As a bonus, it doesn’t require advanced booking.

If you’d like to taste Chianti’s wine (and you really should) but can’t agree on a designated driver, take a day tour from Florence and stay an extra night there. It’s definitely a good idea because, as we all know, drinking and driving is a really bad idea. Plus, the wine is so good in Chianti that you may find it hard to just taste a couple!

Be sure to also visit Radda and Castellina in Chianti, two beautiful Chianti villages on the way.

Wine tours from Florence

El Duomo Siena

Siena ( 1 day)

Siena is another one of Tuscany’s jewels. With its narrow cobblestone streets and its gothic architecture, Siena is a great town to walk around. You’ll feel like you’re in an open-air museum! Then there’s the stunning Duomo (cathedral) which you absolutely must visit. The exterior of the Duomo is pretty nice but its interior will leave you speechless.

Take some time to sit down and relax, admiring the beautiful and bustling Piazza del Campo.

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Piazza della Cisterna, San Gimignano

Volterra and San Gimignano (1 day)

Volterra and San Gimignano are two hilltop medieval towns that are only a short drive from each other. You can visit both in the same day.

Start with Volterra, where you can first stroll around its historic town centre, before visiting its cathedral and Baptistery. Don’t forget to check out the Roman Theatre.

San Gimignano is a real stunner! It’s famous for its fourteen medieval towers that rise high above the beautiful Tuscan countryside. Make sure you climb up the Torre Grossa for some spectacular views and visit its Duomo for some pretty amazing frescoes.

San Gimignano is also the home of the Vernaccia wine variety, so you can’t visit without doing a quick tasting at the Vernaccia Wine Experience, in the La Rocca building inside the walls. As a bonus, La Rocca has some great views to go along with your wine.

Read more about San Gimignano here

Like Siena, San Giminagno is also a good place to base yourself in southern Tuscany.

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Colle Val D’Elsa

Monteriggioni and Colle Val D’Elsa (1 day)

Monteriggioni is nestled between Siena and Colle Val D’Elsa. It may be small, but it’s one of the most impressive walled medieval towns in Tuscany. This tiny village is entirely surrounded by those old walls (which are mostly still intact) and it is protected by fourteen towers. The best part is that it’s not very touristy because, for some reason, it’s not in the guide books!

Colle Val D’Elsa is another beautiful Tuscan town with a lovely old town and great views. It’s also well known for its crystal glass production.

Val D’Orcia

Val D’Orcia (1 day)

Time for another road trip, this time to the Val D’Orcia region. After checking out San Quirico d’Orcia, follow the scenic road SR146 in the direction of Montepulciano, enjoying the beautiful scenery along the way. Make a stop at Pienza and marvel at the green rolling hills and Cypress trees. For a good photo-op, make sure you stop at the Capella della Madonna de Vitaleta, one of Val d’Orcia’s icons.

Once in Montepulciano, explore the old town and don’t forget to visit the historic cellar of De’ Ricci. The entrance is free and so is the tasting (for the first three wines). The wine is really good, especially the Vino Nobile di Montepulciano.

Arrezzo and Cortona (1 day)

Head to the beautiful town of Arezzo. You can visit the Basilica of Saint Francis and enjoy the outstanding frescoes by Piero della Francesca. Then head to the Piazza Grande, the famous piazza from Roberto Benigni’s “La Vita è Bella”.

Cortona is another hilltop town in Tuscany that has amazing views in all directions. This small town was made famous by the book ‘Under a Tuscan Sun’, which was later made into a movie.

Beautiful Lucca

Lucca (2 days)

Now it’s time to head to the North of Tuscany, making your way to Lucca. Lucca is our favourite town in Tuscany and it’s a great place to base yourself for the next few days. We just loved this beautiful, colourful town. Although you can see all of Lucca’s sights in one day, we suggest you spend an extra day there to just enjoy the atmosphere. You won’t regret it.

Climb the towers, visit some of the town’s many churches, sip a cappuccino at the Piazza dell’Anfiteatro and last, but not least, hire a bike or walk around the length of the city walls.

You can read more about Lucca here.

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The Devil’s Bridge, Borgo a mozzano

Borgo a Mozzano and the hilltop villages of Svizzera Pesciatina (1 day)

Not far from Pescia (a small town that is worth a quick visit as well), the mountain area of Svizzera Pesciatina is home to ten little villages known as “The 10 Castella” (The Ten Castles). These villages are all built out of Pietra Serena stone and are set up on hilltops. Each village has its own charms and they all offer fabulous views of the surrounding countryside.


The ten villages are Fibbialla, Medicina, Aramo, Sorana, San Quirico, Vellano, Castelvecchio, Stiappa, Pontito and Lignana (which is mainly in ruins). You can visit them all or simply pick a few of them to get a feel for the area. Either way, you’re in for a nice day of village hopping!

On the outskirts of Borgo a Mozzano, twenty kilometres from Lucca is the famous and highly Instagram-friendly Ponte della Maddalena, also known as the Devil’s Bridge.

The Leaning Tower of Pisa

Pisa (1 day)

What to do on your last day in Tuscany? Did we forget something? What about Pisa? As touristy as it is, you really can’t leave Tuscany without seeing the Leaning Tower of Pisa! So, spend your last day in Tuscany exploring Pisa.

But Pisa is not just about the leaning tower. The town centre is actually quite nice too and has a lot fewer tourists. Take a stroll along the Arno river promenade and then head to the Borgo Stretto for some last minute shopping!

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Incredible Tuscan scenery!

What if you don’t want to hire a car?

Hiring a car will certainly make exploring Tuscany a whole lot easier. It will give you much more freedom and the flexibility to reach some of the smallest hilltop villages that have limited access to public transport.

But not everyone feels comfortable driving in a foreign country and if hiring a car is not for you, we recommend basing yourself in Florence. Florence is well served by public transport, so you will still be able to reach most of the above places from it. There are also many organised day trips that leave from Florence if you prefer to take a tour.

Read more

How to Spend 48 Hours in Florence

5 Things to do in the Tuscan Hill Town of San Gimignano

A Two-Week Itinerary for TuscanyA Two-Week Itinerary for Tuscany

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