Arrival into Pisa airport and transfer to San Gimignano (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 the local area and get prepared for your first day of cycling.

• Meals: Breakfast
• Ascent: 500 Metres Approx.

The fascinating town of San Gimignano is the town of towers and 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 where you can enjoy an evening drink. We recommend watching the sunset from the bastions overlooking the hills of Tuscany.

• Meals: Breakfast
• Ascent: 450 Metres Approx.

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. ‘Isola’ refers to an island or the only solid piece of land on which the original ancient hamlet was built. The Abbey of St Salvatore was founded in the 11th century and was an important strategic crossroad on the Via Francigena between Florence, Fiesole, Siena and Volterra. Now the Abbey is surrounded by flat fields filled with sunflowers in summer, and it’s an easy-going and enjoyable cycle from your accommodation.

• Meals: Breakfast
• Ascent: 600 Metres Approx.

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.

• Meals: Breakfast
• Ascent: 500 Metres Approx.

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 past vineyards towards Gaiole in Chianti, where you can take a slight detour to visit the town. The birthplace of Chianti Classico, Gaiole is celebrated in its own right.

In medieval times it was one of the three capitals of the Chianti League, along with Castellina and Radda. The hilltop town is set among oak and chestnut forests but also surveys vineyards and olive groves. As a former military stronghold, Gaiole is ringed by medieval castles and fortified abbeys. Today Gaiole is also known as the birthplace of the “Eroica” (1997) a vintage cycling event, that brings thousands of riders in the region cycling along the “strade bianche“. Gaiole is a perfect stop for a long lunch, before cycling back to Radda in Chianti.

• Meals: Breakfast
• Ascent: 500 Metres Approx.

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, the landscape changing 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.

• 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.)