A Cycle Holiday To Tuscany

Arriving in Florence today we transfer to our hotel in Castellina in Chianti, a hilltop town with Etruscan and roman origins. We will have time for a briefing over tea before we settle into our rooms. Time to relax and unwind, prepare our bikes for the coming week and enjoy our first evening meal (not included).

Overnight Standard Hotel

Today we tour Chianti, taking the quiet lanes and roads that pass the local vineyards and large fattorias producing the local Chianti Classico wine. Taking a scenic route that traverses quaint medieval villages, we are treated to some striking views of the surrounding hills, blanketed by yet more vineyards and forests of chestnut and oak. We head first towards San Donato and the old Monastery of Badia di Passignano. Our route takes us past a number of the castles that abound in this region, as well as the villages of Greve and Panzano. Eventually arriving back in Castellina with the option for some wine tasting in the village.

Total cycling distance approximately 56km.

Overnight Standard Hotel Included meals: Breakfast

Starting early after breakfast, we descend from the hills to the busy town of Poggibonsi where we stop for a mid-morning coffee break. We continue along a scenic route past sunflowers and vineyards. The approach to San Gimignanao is greeted by the magnificent sight of the thirteen towers of this medieval town, perched majestically on the hilltops above. San Gimignano is a beautifully preserved example of a classic Tuscan Medieval town.  Situated on the old Lombardy to Rome Pilgrim route, it prospered during the 12th and 13th centuries, until a combination of local aristocratic rivalry and the arrival of the Black death devastated trade. Stopping here for lunch there should be ample time for a look around this fine old town, and perhaps indulge in some excellent ice cream as well. After lunch we continue along a scenic back route to the beautifully preserved fortress town of Monteriggioni, admiring some fine views back towards San Gimignano along the way. We end our ride in Monteriggioni with time to explore this picturesque walled village, before we transfer back to Castellina by bus. Anyone feeling particularly energetic can cycle the 14km back to Castellina, which is mostly uphill.
Total cycling distance approximately 61km (plus 14km optional at end)

Overnight Standard Hotel Included meals: Breakfast

Leaving Chianti this morning we head for Siena, an atmospheric city with magnificent Gothic architecture and medieval alleyways. Passing first through the famed wine estates of Fonterutoli we continue onto Radda along gravel tracks and forests. We then arrive at Castel di Brolio in time for lunch in a small local café (not included). After lunch we head towards Castelnuovo di Berardenga, before taking a back road, via Monteaperti, to Siena itself. Arriving sometime in the mid afternoon should give us time to have a look around the city and perhaps enjoy a drink in the Piazza del Campo, the focal point of the city, a semi-circular piazza surrounded by ancient buildings and overlooked by the 100m bell tower (Torre del Mangia). Once a rival to Florence in power and trade, Siena controlled the trade routes between France and Rome, as well as the southern Tuscan wool industry. The Black Death marked the beginning of a decline for the city, decimating it in the 14th century and killing a third of its population. Today it stands as a classic Italian city, with its magnificent central square and the awe inspiring grandeur of the Duomo overlooking the Via di Citta.
Total cycling distance approximately 54km.

Overnight Standard Hotel Included meals: Breakfast

Today is free to spend at your leisure. You may wish to explore the delights of Siena. The centre of this city is traffic-free, making it ideal to wander around on foot, soaking up the many intriguing sights. The Piazza is also used for a horse race twice a year – the famous Palio, when horses and their riders hurtle dangerously around the square to the delight of the crowds. Alternatively you may prefer to visit Florence, the spiritual home of the Renaissance and considered to be one of the most beautiful cities in Italy. Florence is a city of superlatives: from the Ponte Vecchio, the oldest and most famous bridge in Florence and the only one that was not demolished during the German retreat of 1944, to the religious centre of the city and the Cathedral of Santa Maria del Fiore with its giant dome or 'duomo'. Close by are other artistic wonders, including the Baptistry, the East door (called the Gate of Paradise by Michelangelo) and Giotto's famous bell tower, as well as the Piazza della Signoria.  For those of you that might prefer something a little more relaxing there is also the Treno Natura, a special old train that runs from Siena towards Southern Tuscany, dropping people off along the way and picking them up later for the return journey back to Siena. Plenty to choose from!

Overnight Standard Hotel Included meals: Breakfast

Leaving Siena this morning we head out along quiet back roads, our journey enhanced by some wonderful views back towards the city. From here we enter an area known as Le Crete, the badlands of Tuscany with classic scenes of rolling landscape lined with Cyprus trees and farmhouses perched on the hilltops. We continue south, via Murlo, with fine open country around us as we enter the wine producing area of Brunello of Montalcino. From Buonconvento we ride along gravel roads with commanding views of the Val D'Orcia region as we make our way towards Torrenieri and our final section of road along the old medieval pilgrimage route of the Via Francigena to San Quirico where we base ourselves for the next two nights. The terracotta-paved streets of San Quirico D’Orcia are home to some stunning architecture including the delights of the Collegiata, with its ornately carved Romanesque portals, and the church, dedicated to St Quiricus.
Total cycling distance approximately 62km.

Overnight Standard Hotel Included meals: Breakfast

From hill top San Quirico, we take a lovely scenic road, with views in all directions and plenty of stops for photos en route. We ascend to Pienza for a coffee break and a chance to sample some of the great Pecorino cheese here and even a Porchetta roll. The birthplace of Pope Pius II, Pienza’s piazza was transformed into a Renaissance centrepiece when the pope commissioned the architect Bernado Rossellino to build a Duomo, papal palace and town hall. From Pienza, we head onto Montepulciano where we have freetime for lunch and sightseeing. Continue to the medieval hamlet of Montichiello, en route we descend one the of most photographed Cyprus avenues in Tuscany from where we head to the town of Bagno Vignoni, a tiny medieval spa town built around a thermal pool, whose healing properties have been well known since Roman times. After relaxing here and an optional dip in the thermal waters, we ride our final section on bike - back to San Quirico.
Total cycling distance approximately 54km.

Overnight Standard Hotel Included meals: Breakfast

Today we transfer back to the airport in Florence where our tour ends.

Included meals: Breakfast