Arrival in Florence and transfer to Colle Val d’Elsa (either by private taxi or public transport), where you settle in your hotel in the old town, known for its perfectly preserved “tunnel” streets and for its crystal ware. According to your arrival time, you can go for a short visit to the town centre.
Total walking time: around 1 hour + sightseeing time
The first day walk takes you at first through the whole historical town centre of Colle Val D’Elsa, perhaps not as famous as other Tuscan towns, but with a very interesting centre. Then you descend into the valley where you pick up one of the supposed routes of the ancient Via Francigena. Along this route, through a pleasant hilly landscape of vineyards and forests you reach the small hamlet of Bibbiano. Another descent brings you down into the valley of the river Foci. Follows a short stretch through the river valley and past an old water mill. Then you start to climb up along a comfortable track up to the beautiful agriturismo, where you will spend the next two nights. Be sure to be there on time, to enjoy its fabulous setting and surroundings, and perhaps its library or swimming pool. For those who want there is also a longer option to walk to here. Dinner at the private restaurant is included tonight.
Total walking time: around 3,5 hours + sightseeing time (4-5 hours with extra option).
After breakfast you begin your walk to San Gimignano, directly from the agriturismo. First make your way up along the ridge to the small hamlets of Ciuciano and San Donato, passing along several old ‘pievi’ (countryside churches) and villa’s and often with wonderful views of the skyline of San Gimignano. This town – sometimes referred to as having the only “skyscrapers” in Tuscany – is an absolute must, a wonderful medieval city with picturesque vineyards, olive and cypress groves on either side. You have time to explore this small romantic old town with towers that remain from medieval times. The town once had 52 of these towers (there are now less than a dozen). Wealthy, prominent families would use the height of these towers to distinguish themselves, and the towers also served to alert the inhabitants of this walled town of approaching friends and foes. Do make a nice stroll along its impressive medieval town walls. In the town itself there are numerous places to enjoy lunch. Then you follow the Via Francigena back to your agriturismo: first to the convent of Monte Oliveto, located on a wide ridge, then down to a small stream, which you have to cross, before you climb back up to your agriturismo. At night you have another good meal at the agriturismo.
Total walking time: around 4 – 5 hours (+ circa 1 h. in San Gimignano – various options).
Today you leave the agriturismo, heading for Monteriggioni, defined by Dante as a crown in the landscape. The walk first brings you down into the river valley, and then more or less following the Foci, you reach one of the most wonderful Romanesque churches of Tuscany, la Badia a Conèo. The next stop is Quartaia, followed by Gracciano, once one of the most important wheat towns of Tuscany. Another short stretch brings you to the Badia ad Isola, once an important stop on the medieval Via Francigena, and a very intriguing building. The final destination for today is Monteriggioni, where you’ll have the time for a drink in the square. Then you are picked up by your taxi and transferred to Siena, where you settle in your centrally located hotel, and just a few minutes away from the famous ‘Piazza del Campo’. In the evening you can take a nice stroll into town to have dinner in one of the many nice restaurants, or sip a drink in the ‘Piazza del Campo’.
Total walking time: around 5 hours + sightseeing time.
Optional extra day
Take your time to explore Siena, one of Italy’s most beautiful medieval towns. Its heart is the perfect, shell shaped Piazza del Campo, scene of the Palio, its Palazzo Publico with pictures and frescoes including Lorenzetti’s ‘Good and Bad Government’. There is also a cathedral built in 1196-1216 with the remarkable Libreria Piccolomini, decorated by Pinturicchio. See the Medieval Duomo of black and white marble, Museo dell’Opera with Duccio’s Maestà, the list goes on and on….
Today you first make a short train ride to Asciano, a beautiful, yet unknown, walled town. From here you start your walk in southern direction. You cross the fascinating area of hills called the Crete Senesi and you reach the Monastery of Monte Oliveto Maggiore, built in the 14th century by the Olivetan monks. Surrounded by a forest of cypresses, this place is world-famous for the frescoes in the courtyard painted by the 15th century painters Signorelli and Sodoma. Even the library and the church of the convent are architectural masterpieces. The walk is relatively short so there is time to visit both the charming village of Asciano and the monastery. You settle in one of the quiet, comfortable rooms. In the evening you dine in the nearby restaurant in the old entrance tower.
Total walking time: around 4,5 hours + sightseeing time (5,5 hours with extra option).
From the Convent of Monte Oliveto you first walk uphill to the small village of Chiusure, in a commanding position on a ridge, with a wonderful view on the monastery of Monte Oliveto and the whole area of the ‘Crete Senesi’. Then you continue your walk, mostly downhill, to Buonconvento, another walled medieval town. Crossing olive tree fields along woodland tracks and so called ‘strade bianche’ (‘white’ gravel roads), you will eventually reach this small town, where the Emperor Henry VII died in 1313. From here you have the possibility to either continue the walk or take the bus to Montepulciano, where you stay the last two nights.
Total walking time: around 3,5 hours + sightseeing time (shorter option: 1,5 – 2,5 hours).
After breakfast you walk down the medieval alleys of Montepulciano to the impressive Chiesa di San Biagio, a 16th Century church nestled at the edge of the village walls, overlooking the winding valley below. From here you commence our walk into the picturesque valley and through vineyards, olive groves, past pastel coloured villas and across rolling hills. This is a morning of delightful Tuscan scenery enjoyed and experienced at its best – by foot. You then reach the restful village of Montichiello, where you can enjoy a flavoursome lunch under the welcome shade of creeping grapevines with a stunning view out upon Montichiello’s ancient main village gateway.
After lunch you can either continue the walk and reach the wonderful Renaissance town of Pienza, or join the locals on a short local bus ride back to Montepulciano and then enjoy a sightseeing tour of its labyrinthine maze of alleyways and laneways and imposing defensive walls. The rest of the afternoon is then at leisure to explore and perhaps shop amidst Montepulciano’s classy boutiques.
Total walking time: around 3,5 hours + sightseeing time (5,5 hours with extra option).
End of the tour. From Montepulciano it’s easy to return to either Rome or Florence.