Tuscan Trails (self-guided)

Day 1: Arrive Colle Val d'Elsa

Your trip starts with your arrival in Colle Val d‟Elsa, situated in the heart of Tuscany. The town is accessible by private taxi or public bus from Florence (52km) or Siena (27km). The closest airports are Florence (1 hour) or Pisa (2 hours). After settling into your hotel, which is located in the old town, you may wish to take walk around the town centre, known for its perfectly preserved tunnel like streets and its crystal ware.

Day 2: Colle Val d'Elsa - San Gimignano

Your walk today takes you at firstly through the whole historical town centre of Colle Val D‟Elsa, perhaps not as famous as its neighbouring Tuscan towns, but with a very interesting old town centre. You then descend into the valley where you pick up one of the 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 to the valley of the Foci River with a short stretch through the river valley and past an old water mill. You then start to climb up along a comfortable track up to a beautiful ‘agriturismo’ (farm estate), where you will spend the next two nights. It’s recommended you start early today to make sure you have plenty of time at the property to enjoy its fabulous setting and surroundings, and perhaps its library or swimming pool. For those who wish there is also a longer option to walk to this point. Tonight dinner is included at the private restaurant of the agriturismo. Total walking time: approx 3.5 hours + sightseeing time (4-5 hours with extra option). Meals included: 1 breakfast, 1 dinner

Day 3: San Gimignano

After breakfast, directly from the agriturismo, you begin your walk to one of Tuscany’s most treasured towns - San Gimignano.. You firstly make your way up along a ridge to the small hamlets of Ciuciano and San Donato, passing by several old ‘pievi’ (countryside churches) and villas and 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 magnificent medieval city with picturesque vineyards, olive and cypress groves surrounding it on all sides. You have time to explore this small romantic old town with its 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. A stroll along the town’s impressive medieval town walls is a must. In the town itself there are numerous places to enjoy lunch. We then 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 will cross before you climb back up to the agriturismo where you’ll spend another night. Another chance tonight to sample something different from the sumptuous menu of the restaurant. Total walking time: approx. 4 – 5 hours Meals included: 1 breakfast, 1 dinner

Day 4: Monteriggioni

Today you bid farewell to the agriturismo and head for Monteriggioni, defined by Dante as a crown in the landscape. The walk first takes you down into the river valley, and then you follow the Foci and eventually 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 a 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 time for a drink in the square. We will then be picked up by a taxi and transferred to Siena, where you settle in your centrally located hotel, just a few minutes away from the famous Piazza del Campo. In the evening you can enjoy a nice stroll into town to have dinner in one of the town’s many restaurants, or perhaps a drink in the Piazza del Campo. Total walking time: approx. 4-7 hours (4 hours for shorter options available) + sightseeing time. Meals included: 1 breakfast

Day 5: Monte Oliveto

Today you take a short train ride to Asciano, a beautiful, yet unknown, walled town. From here you start your walk in a southerly 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 and 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). Meals included: 1 breakfast, 1 dinner

Day 6: Montepulciano

From the Convent of Monte Oliveto you 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. You continue your walk, mostly downhill, to Buonconvento, a walled medieval town. Crossing fields of olive trees, woodland tracks and ‘strade bianche’ (white gravel roads) you will eventually reach the small town, where the Emperor Henry VII died in 1313. From here you have the possibility to either continue the walk or take a local bus to Montepulciano, where you stay the last two nights. Total walking time: approx. 3.5 hours + sightseeing time (shorter option: 1.5 – 2.5 hours). Meals included: 1 breakfast

Day 7: Montepulciano - Pienza

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 your 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, experienced at its best on foot. You then reach the restful village of Monticchiello, where you can enjoy a flavoursome lunch under the welcome shade of creeping grapevines with a stunning view out upon Monticchiello'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 at leisure to explore and perhaps shop amidst Montepulciano's classy boutiques. Total walking time: approx. 3.5 hours + sightseeing time (5.5 hours with extra option). Meals included: 1 breakfast

Day 8: End Montepulciano

End of the tour. From Montepulciano there are buses to the train stations of both Montepulciano and Chiusi, from where there are regular trains to Rome and Florence. Meals included: 1 breakfast