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Florence and Tuscany
Tuscany walking journey

DAY 1 - Under the Tuscan Sun: Cortona of course!

Benvenuti! A driver will wait for you at the Florence airport/train station for your transfer to Cortona. Relax and make yourself ready for your first easy walking that will start in Terontola, a small village over Cortona. Set on one of the slopes of Mount S. Edigio that overlooks the Val di Chiana, this little town still retains its Etruscan and Medieval walls that enclose fine stone buildings, narrow paved perpendicular streets, as Romans used to do, or windy medieval streets, with the result of beautiful sights and enchanting views. While your baggage will be carried at your hotel, you'll meet our guide Giovanni and start your walk on the paved track over the Roman remnants of Ossaia, a toponym that takes its name from the ancient war against Hannibal. This trail running in the woods of the Cortona hills, offers, halfway, a stunning view over Cortona and the Valdichiana. At the end detour to your hotel for your first night under the Tuscan sky.


DAY 2 - Cortona and view of Val di Chiana

Today your walk will detour from Cortona up to Le Celle, the Franciscan Hermitage, located just above Cortona and hidden among ancient trees: founded by S. Francis in 1211, it still retains the magical atmosphere of all Franciscan places. On the way back we will pass by Frances Mayes famous house. The Val di Chiana produces some pretty good wines now, but it is mostly renowned for one of the highest quality olive oils of Tuscany. Today we will visit one of the few remaining olive oil mill, in the Cortona area, that continues to operate a traditional, cold stone milling process, run by the same family since its foundation in 1875.


DAY 3 - Pienza and the iconic Val D'Orcia

A quick transfer to Montepulciano and ready to start our walk to Montechiello and onto Pienza, looking over UNESCO Val D'Orcia. The walk will take us through the rolling wheat fields, we will then reach the Pieve of Corsignano an enchanting Romanesque parish church, before walking up to Pienza, since 1996 recognised by UNESCO for its fine Renaissance architecture, and inscribed onto their world heritage list. The place, with its calm and quaint atmosphere has inspired more than an artist, among them Zeffirelli who filmed here its famous version of Romeo and Juliet.


DAY 4 - Pienza - Siena: Tuscan dreams are made of this

A quick transfer among the quintessentially Tuscan scenery will take you to Siena today: rolling hills carpeted with olive groves, vineyards and a patchwork of verdant green and mellow ochre fields, beautiful, isolated, hill-top farmhouses dot the landscape, and short lines of cypress trees reach up towards the warming sun. That is what a dream of Tuscan is made of. You will start our walk before Siena and you'll reach on foot through Porta Romana, the hotel at the heart of town. Later in the day you can explore on your own this imperious city. Set on three hills, the city is drawn together by winding alleyways and steep steps, whilst the Piazza del Campo stands at its heart, and the Duomo and St Maria della Scala serve as additional cultural landmarks.


DAY 5 - Siena: a time-capsule city

After breakfast, meet your guide for a walking tour of the city. Siena was a very remarkable City-State in the Middle Ages, most of its important monuments were built between the XIII and the XIV century, today we can still admire these artistic and architectural wonders and much more. There are so many hidden spots within the city walls where past and present blend together and your guide is with you to discover the best off beaten path!


DAY 6 - Florence: Renaissance at large

After breakfast, check out and transfer to start our morning walking to Florence, through the hilly region between Florence and Siena, so beautiful for its vineyards interspersed among woods, where hamlets and fortified castles are memories of an old and glorious past. You'll also learn a lot about Chianti wine. At the end there will be a transfer to Florence. Check in at your hotel. The rest of the day is for you at leisure.


DAY 7 - Florence at your pleasure

After breakfast, meet with your guide for a guided introduction to Florence's current and past history. Born and raised in this remarkable city, your Florentine guide leads you through Piazza della Signoria, an open-air museum and ideal introduction to the Renaissance and its priceless sculptures. You then make your way to the other most historic square, Piazza del Duomo, a colorful riot of inlaid marble and stones. Here, you may want to admire Ghiberti's Gates of Paradise, sharing well-known stories through each of its incredible bronze panels. Your well-earned thirst is rewarded with an aperitivo (or a gelato!) in one of the most famous cafes. The rest of the day is for you to relax and explore on your own this marvelous city.


DAY 8 – Departure

After breakfast, check out at your hotel. A private transfer has been organized according to your flight departure.


  • From
  • Start / Finish Florence / Florence
  • Activity Level Amateur hikers
  • Length 8 / 7


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