A Two Weeks Itinerary in Tuscany

A great Two Weeks Itinerary in Tuscany to discover the best of the region

Have you ever been to Tuscany? If not, you’ll find it is an amazing country:-) There are a lot of good reasons to visit Tuscany and pass a great holiday! and this fantastic Two Weeks Itinerary in Tuscany can be very helpful.

Are you going to stay in Tuscany for more than just a few days? You are in the right place!

As some American friends have been asking me how to plan a two weeks vacation in Tuscany, here is the travel itinerary I suggest to explore Tuscany’s amazing and exceptional sights at its best. Two weeks is actually the right time to get the most out of this beautiful region of Italy.

Renting a car or not?

A car is definitely required, at least after you’re leaving Florence, considering the secluded location of many of the smaller suggestive villages, that cannot be reached by public transportation but are all waiting for you to be explored.

As you are going to travel by car, you may well stay in some nice and peaceful hilltop villages amid the scenic Tuscan countryside for most of your stay.

On the contrary, if you are not going to rent a car at all, base yourself in Florence, that is well served by public transportation, having a central location in Tuscany. If that’s the case, here are the Best Day Trips from Florence.

Let’s start with our itinerary! Spend the first 3 days in Florence, as you will probably be flying from abroad to Florence or Pisa airports, and then move to 2 different hill towns and use them as your base.

Two weeks in Tuscany Itinerary

1. Three Days in Florence beautiful historic center

 

For the first three days of your holiday, I’d suggest you stay right in Florence’s historic center, so to visit and appreciate as many attractions as possible. Florence is the cradle of the Renaissance, the city of art at its highest levels, the city of the David by Michelangelo, the city of Dante Alighieri…and nowadays also the perfect place for a great shopping 🙂

From the Uffizi and the Ponte Vecchio to the church of Santa Maria Novella, the Cupola del Brunelleschi and Palazzo Pitti, Florence retains so many unexpected treasures and such impressive sights, that one lifetime wouldn’t be enough to visit all it has to offer.

Where to stay in Florence:

There’s a full article dedicated to the Top Attractions to visit in Florence, and one with my personal recommendations about Florence Best Hotels and Charming Accommodations. Hotel Brunelleschi is particularly amazing, being also a museum!

Pisa and Lucca

Staying 3 nights will give you the possibility to get the best of Florence, and since you are there, do visit Lucca and Pisa on a day trip from Florence using the train. There are in fact fast trains running from Florence to Pisa in just one hour. Florence Santa Maria Novella train station is in the town center so it’s very convenient. You can find train timetables at www.trenitalia.com.

Pisa is a must visit and not just for its famous Leaning Tower! All the Square of the Miracles is a unique incredible work of art! Lucca with its impressive circle of walls, a fantastic round square that is an ancient Roman theatre, the wonderful churches and the many charming shops, cannot miss from your itinerary as well.

Tips on moving around Florence’s center

Once in Florence you can conveniently explore the town also on foot, as the historic center is quite small, and all the main sights are walking distance. A good alternative is to move around by bus. ATAF is the public bus company in Florence. For more information about bus routes, tickets’ fares and much more, visit ATAF official website.

Renting a car once in Florence

While in Florence do use public transportation to get around and not the car, there’s a lot of traffic, driving can be quite stressing and there is little and expensive parking. Once you are leaving Florence to explore other parts of Tuscany pick up your car at your rental company in town.

Cars can be picked up at Florence airport (in this case you can take the car directly at the airport and spend in Florence not the first but the last 3 days of your trip) , or in Florence downtown, near the Santa Maria Novella train station. You can rent your car online here.

2. San Gimignano as a base for your holiday

 

After you have visited Florence, pick up your car and start to explore the beautiful countryside driving up and down Tuscan hills, until you get to San Gimignano, wonderful hill town famous for its scenic 14 medieval Towers, where you could stay 5 or 6 days. San Gimignano itself has much to offer, here you can read about all of San Gimignano’s Top Attractions I suggest to visit, from the beautiful paintings at the Museo Civico, to the stunning panorama from the Torre Grossa, to the Torture Museum and the stunning frescoes in the Duomo.

From San Gimignano you can then start to make fantastic day trips:

• Chianti, charming countryside, green hills and vineyards, known worldwide for its fine Chianti Classico wine and its lovely hill towns, like Castellina in Chianti. Having the car here is great! Enjoy driving through Chianti panoramic and winding routes.

• Volterra, beautiful Etruscan town enjoying a stunning hill-top location on a spur of tuff in perfect isolation, here you can admire the exceptional remains of its Roman theatre, wander its characteristic alleys and visit the stunning Etruscan museum.

Where to stay in San Gimignano:

I recommend the B&B Locanda Viani, right outside the city walls with a stunning view over the towers, or, if you prefer to stay right within the town’s walls, choose Hotel Antico Pozzo, elegant 3 star hotel.

Where to park in San Gimignano:

As you are traveling with your own car, it can be useful to now where to park in San Gimignano. The historic center of San Gimignano, that is enclosed within the walls, is a limited traffic area, so the hotel you’re going to choose will have to give you special permission to get in front of it to load and unload your luggage. In the case of Hotel Antico Pozzo the car park is number 3, have a look here. While, if you are staying stay at Locanda Viani, just outside the city center, you will have the parking in front of your accommodation.

There are 3 main public car parks in San Gimignano, here you can have more detailed info about Parking in San Gimignano.

3. Two or Three days in Siena, not just the city of the Palio

Before heading on to Montepulciano, you may also spend 2 or 3 days in Siena, so to have the right time to visit most of Siena’s incredible sights. Staying in Siena’s historic center is an experience! Also thanks to its hill top location amid a stunning natural landscape, Siena is probably the most beautiful major art town in Tuscany, literally!

From the amazing shell shaped Piazza del Campo with the imposing Torre del Mangia, passing through the wonders of the Duomo, like the Piccolomini Library and the frescoes by Pinturucchio, arriving to the interesting Museum at Santa Maria della Scala. While staying in the very heart of the historic center, you will have the possibility to admire Siena Top Sights and Attractions. Just outside Siena is Monteriggioni, medieval town with a perfect circle of walls all enclosing its suggestive tiny center.

You can find a post with useful suggestions on the Best Day Trips from Siena

Where to Stay in Siena

I recommend staying at the lovely Relais Campo Regio, right in the town’s center and with fantastic views over the Duomo. It is an elegant hotel with beautiful bedrooms, some with frescoes, and all the main monuments and sights of Siena are all reachable on foot. You can find also further suggestions on Siena Luxury Accommodations here.

Where to Park in Siena:

Siena is again a limited traffic area, you will find that each hotel usually has a garage near it. Any hotel you’re going to book, however, will give you all detailed info on how to reach them, a permission if required, and will guide you to the nearest car park. Find more info about Parking in Siena.

4. Montepulciano as a base to explore southern Tuscany

 

For the last part of your trip I suggest staying south of Siena, in the area known as the Val d’Orcia, magical countryside region and natural park with the most scenic and surprising landscape in Tuscany! That’s where come all of those beautiful postcards you see of the evocative Tuscan countryside 🙂

Use Montepulciano, one of the most beautiful towns of all of Italy, as your base. I suggest you spend here most of your stay, 4 or 5 nights. Located between the Valdorcia and the Valdichina, this impressive hill town is of rare beauty and is perfect to explore that extraordinary part of Tuscany. From Montepulciano, you can make a lot of fantastic day trips to some of the most beautiful sights of southern Tuscany:

• Pienza and Monticchiello: Pienza is not just an exceptional Renaissance village that was built in just 3 years for the want of Pope Pius II, but it’s also the town of the tasty pecorino cheese. Pienza is also one of the most romantic places in Tuscany. On a panoramic hill overlooking Pienza, rises Monticchiello, tiny village with thick walls that retains a suggestive atmosphere.

• Montalcino is an impressive town atop a hill, famous for its Brunello wine. It is dominated by a majestic and panoramic fortress with bastions, wander throug its characteristic alleys and enjoy some shopping 🙂

• The Abbey of Sant’Antimo near Montalcino, that you can visit in combination with Montalcino, is a mystic and incredibly suggestive place, don’t miss it!

• Bagno Vignoni, peculiar hamlet with ancient thermal springs, having a large ancient Renaissance pool as its main incredible square!

• Rocca d’Orcia: climb up its tower to enjoy a breathtaking panorama all over the Orcia Valley.

• Crete Senesi: driving northeast of Montepulciano you’ll find yourself immersed in the heart of the Crete, one of the most impressive and peculiar landscape of Tuscany for their lunar and almost deserted landscape

• Arezzo and Cortona: Arezzo is extremely beautiful! Visit the outstanding frescoes by Piero della Francesca in the Basilica of Saint Francis, the enchanting Piazza Grande with beautiful loggias by Giorgio Vasari, and much more. In Piazza Grande Roberto Benigni also shot some scenes of La Vita è Bella. Cortona, on the very top of a hill overlooking one of the vastest panorama in all of Tuscany, is all to discover, with a stunning Etruscan museum and lovely shops.

• Radicofani: Located at the far end of the Val d’Orcia, Radicofani is a charming village dominated by an imposing fortified fortress, again boasting an incomparable panorama over an impressive landscapes with ravines and hills running one after the other.

• Pitigliano: As you are in Tuscany for 2 weeks, I highly recommend you visit Pitigliano, about one hour and 20 minutes from Montepulciano. That’s one of the most spectacular and peculiar town in Italy, rising right out from the rocks! Next to Pitigliano, also take the chance to visit the small and incredibly characteristic villages of Sorano and Sovana, their atmosphere is really suspended in time, time here seems to have stopped. In Sovana you can also admire an ancient treasure of gold coins, that was accidentally discovered here in recent years!

Many of the hill towns and attractions of the Val d’Orcia can be visited also in one day, say, you could visit Pienza, Monticchiello and Bagno Vignoni in one day. Here you can find my list of the Top Ten Attractions to visit in Val d’ Orcia.

Where to stay in Montepulciano:

I recommend Osteria del Borgo Apartments, offering lovely apartments in typical Tuscan style with an amazing view. Just note, however, that to reach the apartments you will have to make a lot of stairs, as there’s no lift. Another very good and chic alternative could be La Locanda di San Francesco, an exclusive retreat with luxury rooms and amazing view over the Tuscan countryside.

Tuscany Holiday Plan

Planning your holiday in Tuscany? If you need help in arranging your trip or if you have questions as to the best travel itinerary, just ask a question here! I’ll be happy to help!

Tuscany Itinerary 7 Days