Tuscany is one of my favorite regions of Italy. I’ve been several times and keep on visiting because there is simply so much to see! I want to share with you some advice to help you organize your trip and not missing the top of the region.
I have visited Tuscany following this itinerary, so it is proven and approved!
The itinerary is based on a 4 nights stay and transportation based on car and it includes some tips on where to stay. Feel free to change the itinerary in order to fit it to your interests, contact me for further information or help for the organization, I will be glad to help!
DAY 1 – CORTONA
I’ve already talked about Cortona here. Just let me add this suggestion: stay at Hotel San Michele, a 4 stars hotel located in the town center. The hotel is located in an ancient fifteenth century palace that gives the facility this magical and historical allure and creates the fascinating atmosphere tangible in the whole palace. The hotel is few minutes away from Piazza della Repubblica and allows you to discover the town in complete relax.
DAY 2 – AREZZO / SIENA
On this second day of exploration you will discover the city of Arezzo, not far from Cortona, so the journey won’t take a lot. The best way to discover Arezzo is by walk, so park the car and just go explore the city! Stop to visit Piazza Grande and the porticoes of Palazzo delle Logge Vasariane, the Cathedral and the House of Petrarca, the famous Italian Poet.
At the end of your tour begin your journey towards Siena. Depending on when you’ll leave Arezzo, you may have some time to have dinner and having a preview of Siena.
DAY 3 SIENA
I have to say Siena is one of my favorite city in Tuscany and I regret I always manage to spend only one day in the town. In the meantime I think one day is enough to discover all its beauty. Spend a lot of time wandering around Piazza del Campo, the famous square where every year the city hosts the historical Palio di Siena, and get lost around its narrow ancient streets. From the square you can have a look at Torre del Mangia (the tower that overlooks the square), the Palazzo Comunale (Townhall) and Fonte Gaia (Happy Fountain). Save some time to visit the exquisite Cathedral of the city.
Stay at Casale Virgili a very nice Bed and Breakfast located 5 minutes far from the town but surrounded by the beautiful Tuscan countryside. The B&B is in a seventeenth structure and gives the guests the opportunity to have a relaxing stay, it also have a beautiful swimming pool!
DAY 4 SAN GIMIGNANO / FLORENCE
San Gimignano is a one of a kind beauty you won’t find elsewhere. The Medieval Manhattan, as it is called, will surprise you with its story and its peculiarity. The city earned this nickname due to its Medieval towers you can find all over the city. Walking around the town will carry you in another era and the sense of wonder one has at the first sight of the town, will accompany you during the whole stay. Start discovering the town from the very beginning, at the entrance at Porta San Giovanni, and reach Piazza delle Erbe, Piazza del Duomo and Piazza della Cisterna, the very center. Remember to look up, the towers overlook the whole city and take some time to climb Torre Grossa for a very spectacular view of the town and the surrounding countryside. Other highlights are the Cisterna (wheel), Palazzo Comunale and Palazzo del Podestà.
For your stay you can choose from several hotels in the very town centre, all charming and with a magical allure and atmosphere:
But if you don’t mind to stay just outside the town, surrounded by the beauty of nature in the Tuscan countryside, the Hotel La Collegiata is the right place for you!
DAY 5 FLORENCE
I don’t think this city needs a detailed description. Everyone knows at least one of its corner or has dreamed of Florence, personally is not one of my favorite city in Tuscany but indeed is one of the best Italian cities. The Cathedral, Ponte Vecchio, The Uffizi Museum, Michelangelo’s David are only few of the top things Florence has to offer to its visitors.
Choose Hotel Brunelleschi for a super romantic stay in the very city center.
If you have the chance to add a day to this itinerary, consider a Wine Tour in the Chianti, one of Italy’s most famous areas for the production of wine. I really regret I still have to do it. Chianti is full of wineries for tastings and tours in the wine cellars.
Have you got other suggestions or a very special spot you’d love to share?
More photos here: