Today you will arrive into Pisa airport and transfer to Castellina in Chianti (transfer approx. 1.5 hours). Depending on your arrival time and local arrangements, we may arrange for your local representative to meet you either tonight or tomorrow morning to fit you to your rental bikes (if renting) and conduct your welcome meeting. Details will be confirmed for you ahead of your departure.

After checking into your accommodation, you will have the rest of the day to explore Castellina in Chianti which is well worth exploring on foot; its importance is not only connected to wine, but also to the abundance of Etruscan sites found in this region.

• Meals: Breakfast
• Ascent: 620 Metres Approx.

On the first day of your cycling holiday, you will set off from Castellina through verdant, green olive groves and past old, isolated farmhouses surrounded by lush fields and vineyards. You will slowly descend into the Val di Pesa and the village of San Donato, where you may well stop at the Pieve (parish church) to admire the panoramic view of the Chianti landscape.

After a welcome coffee break in the village of Barberino di Val d’Elsa, you will soon reach the hamlet of Vico d’Elsa. From here, you’ll descend to the Elsa River and then cycle up again towards San Gimignano. Soon after, you will see your first glimpse of the towers the little town is famous for. This town of towers is one of the prettiest and best-preserved medieval settlements in the whole of Italy!

San Gimignano is also known for its white wine, Vernaccia di San Gimignano which is grown in this area. We highly recommend taking a walk through its narrow streets – a great opportunity to absorb the Tuscan atmosphere.

• Meals: Breakfast
• Ascent: 740 Metres Approx.

In the morning, you will leave San Gimignano and you will descend towards the plains of the River Elsa Valley. You’ll ride past woodland and cultivated fields, making your way towards the hill-top town of Casole d‘Elsa. The last few kilometres are challenging, however the views from the top of the hill will certainly be rewarding.

Take your time to wander through this authentic medieval town, far away from the tourists and clichés of Tuscany. You will leave Casole d‘Elsa on a rolling road, passing small stone villages scattered throughout the countryside. Sections of the route are part of the Via Francigena, the pilgrimage route from Canterbury to Rome. This ancient road takes you directly to your accommodation near the hamlet of Monteriggioni.

In order to get there, you will first pass through the tiny villages of Strove and Abaddia Isola. The fields surrounding this village were once a large swamp or bog that accumulated rain water from Monte Maggio. ‘Isola’, refers to an island or the only solid piece of land on which the original ancient hamlet was built around the 11th century Abbey of St Salvatore.

• Meals: Breakfast
• Ascent: 420 Metres Approx.

From your accommodation, you will climb to the Castle of Monteriggioni, dating back to the 13th Century. The impressive castle walls can be linked to Dante’s Divine Comedy and once served as a defensive stronghold for the town of Siena against rival Florence.

A stroll through the narrow streets is a must, as well as a cycle round the fortified walls. After descending into the valley again, you will continue your ride south into the Montagnolo hills, just to the west of the city of Siena. Here, you will cycle through open fields, leafy woodlands and small villages, making your way through the hamlets of Volte Basse, Costalpino and Sant‘Andrea a Montecchio to your accommodation in the village of San Rocco a Pilli.

• Meals: Breakfast
• Ascent: 545 Metres Approx.

You will begin your ride today from San Rocco, where you’ll continue cycling through the Val di Merse. This valley forms a natural bridge between the hinterland of Siena and the Tyrrhenian Sea. You will then reach the Crete Senesi, the ‘wasteland’ of Tuscany. The gentle hilly landscape lined with cypress trees is typical of this region.

We recommend that you stop in the Etruscan town of Murlo. It is another small stone-fortified village that is ideal for a coffee or an ice cream break. You then continue cycling towards Buonconvento, situated in the Valley of the Ombrone River. After checking in at your hotel and freshening up, you may well go out for a stroll through the old town and admire its extensive and well preserved town walls.

• Meals: Breakfast
• Ascent: 650 Metres Approx.

Today after setting off from Buonconvento, you will first loop down south in direction of Montalcino and San Quirico d’Orcia, to then change direction and slowly make your way up north again to the village of San Giovanni d’Asso, famous for its truffles!

You are now on the ‘Lautania’ route, once a paved Roman road, travelled by many artists and pilgrims. They all had the same destination, the famous monastery of Monte Oliveto Maggiore with its colorful frescoes. After admiring this work of art and ‘refueling’ your soul and stomach, you will quickly descend onto Asciano, a walled city that has origins in the founding of Rome. According to legend, Remus’ sons, Aschio and Senio, fled the newly founded city of Rome, which was ruled by their uncle Romulus. Aschio then founded Asciano, while Senio founded Siena.

• Meals: Breakfast
• Ascent: 700 Metres Approx

After breakfast on your final day in the saddle, you’ll set off on a stunning bike ride through the spectacularly eroded landscape of the Clay Wasteland of the Crete Senesi, while making your way north in direction of Taverne d’Arbia. Here, you will cross into the hilly country surrounding Siena, the final destination of your cycling holiday.

You will be able to spot the city’s bell towers and churches from far away. A final push will see you entering Siena from the Porta Romana. From here, your route leads you straight to the heart of the city and onto the Piazza del Campo, where the famous Palio takes place.

There will be time to wander through Siena in the late afternoon, with a visit to the Palio Square and the Duomo, before heading out to dinner for a mouthwatering Tuscan meal to celebrate your achievement in style.

• Meals: Breakfast

Today you’ll say ‘Ciao!’ to this beautiful part of Italy and we’ll transfer you back to Pisa airport for your outgoing flight. (Transfer approx. 1.5 hours)