After arriving in Pisa we'll transfer you through Tuscan landscape, arriving at your first accommodation near San Gimignano, one of the many historical towns you'll be visiting throughout the week. The subsequent days will see you following quiet roads, riding past picturesque farmhouses nestled amidst olive groves, vineyards and forests on your way to the medieval towns of Abbadia Isola, Monteriggioni, Radda in Chianti and Siena. With towns oozing the Italian Renaissance atmosphere, scattered with great restaurants, superb gelaterias and the excellent wines of Chianti and Montalcino, there's no better way to explore Tuscany than by bike!
Day 1: Arrival into Pisa Airport - Transfer to San Gimignano (D)
Arrival into Pisa airport and transfer to San Gimignano (transfer approx. 1.5 hours). On arrival at your first accommodation, your local representative will fit you to your hire bikes (if hiring) and conduct your welcome meeting. Now is the perfect time to ask any questions you may have about the week ahead.
Day 2: San Gimignano to Casole d'Elsa (B, D)
Today is a gentle start to your cycling holiday, to give you some time to explore San Gimignano. Leaving your accommodation in the morning, you’ll first ride into the town.
This fascinating 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 the area. The old town is a UNESCO World Heritage Site. We recommend taking a walk through its narrow streets – a great opportunity to absorb the Tuscan atmosphere. Back on the bikes you will descend towards the plains of Colle Val d‘Elsa. 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 but the views from the top of the hill will certainly outweigh the effort. You’ll have some time to wander through this authentic medieval town, far away from the tourists and clichés of Tuscany. The accommodation is set just outside the walled centre, a short walk into town and you have a few trattoria to choose from. We recommend watching the sunset from the bastions overlooking the hills of Tuscany.
Today we include a dinner, however as the hotel’s restaurant is closed on a Monday if your stay falls on this day, we will organise your dinner to be on an alternative day. There are a number of restaurants to choose from in Casole d‘Elsa.
Approx. distance: 18 Miles / 29 Kms
Day 3: Casole d'Elsa to Abbadia Isola (B)
You’ll 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 will lead you straight to your accommodation, in an ancient medieval village, surrounded by vast vineyards; an ideal place to taste the local wines. A short cycle away from your accommodation you’ll find Abbadia Isola.
The fields surrounding Abbadia Isola were once a large swamp or bog that accumulated rain water from Monte Maggio.
Approx. distance: 20 Miles / 32 Kms
Day 4: Abbadia Isola to Radda in Chianti (B)
Today is the toughest stage of the week, with a roller coaster ride through the northwestern side of Siena and into the Chianti region. Don’t worry though, each new climb will be rewarded with a fantastic descent!
The first climb takes you to the Castle of Monteriggioni with its 13th-century architecture. The massive walls here are linked with Dante’s Divine Comedy and, at that time, served as a defensive stronghold of the town of Siena against rival Florence. A gentle stroll through the narrow streets is a must, as well as a cycle round the fortified walls. Back on the bikes, you’ll head towards Castellina in Chianti. You will soon realise you are cycling in wine territory as you pass acre after acre of vineyards. Castellina in Chianti 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.
Such rich archeological heritage justifies a visit to the territorial museum for Chianti Senese, its collection including findings not only from the township of Castellina in Chianti, but from Castelnuovo Berardenga, Gaiole in Chianti and Radda in Chianti as well. Leaving Castellina, another 11 Kms will take you to Radda in Chianti, a beautiful medieval town enclosed in large defensive walls.
Approx. distance: 19 Miles / 31 Kms
Day 5: Radda in Chianti to Siena (B)
Today’s route will be a gentle roller coaster through the Chianti region of oak forests and vineyards. The day will start with a gentle descent towards Gaiole in Chianti, where you can take a slight detour to visit the town.
Moving south again, the landscape will change from oak forests to cultivated fields as you make your way towards Siena. This whole region is dotted with castles, once defensive systems but now privately owned by wine producers. Your route will then take you past Meleto, San Donato in Perano and Brolio Castle. You’ll follow a mixture of tarmac and “strade bianche” (gravel roads) as you get closer to Siena, with glimpses of bell towers and churches.
Entering Siena from the Porta Romana will lead you straight to the heart of the city, 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.
Approx. distance: 27 Miles / 43 Kms
Day 6: Exploring the Colline Senesi (B)
Last chance to explore this stunning region as you head off on your bikes to explore the famous “Colline Senesi”. The colline is what we associate Tuscany with; rolling green hills, lined with Cypress trees with a villa on the hill top. Formed mainly of a chalky terrain, the riding today will be an exploratory route to Asciano and on to Buonconvento where you can take the train back to Siena. This is your last evening in Tuscany, and what better way than to sit in Piazza Campo for a pre-dinner drink?
Approx. distance: 30 Miles / 49 Kms
Day 7: Departure from Siena - Transfer to Pisa Airport (B)
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. 2 hours.)
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Rolling green countryside will be the backdrop for most of your Tuscany cyling holiday and you'll have the chance to explore the Chianti region and the Crete Senesi which are among the most classic and beautiful areas in the whole of Tuscany.
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