After transferring from Pisa airport you will check in at your hotel in Volterra. Located just a short distance away from the old part of town, you should have time (depending on flight times) to walk around and enjoy your first day in Tuscany. In the evening you can enjoy a nice dinner full of local specialties and meet the other members of your group. (Transfer approx. 1.5 hrs).

• Meals: Breakfast, dinner

We’ll leave the walls of Volterra behind us and will soon embark on a breathtaking descent. Riding past isolated farmhouses surrounded by green fields, between rows of olive trees and cypresses, we’ll soon be well acquainted with just how beautiful this part of Italy really is.

We’ll follow the Val D‘Elsa on a rolling road that will take us from rural countryside to a more mountainous area of dense forest. We are now in the ‘Oasi Naturale di Castelvecchio” whose special micro climate has allowed the existence of a strong biodiversity and the survival of rare bird species such as the peregrine falcon.

Pedalling on, the view will open up and we’ll get a glimpse of the towers of San Gimignano. 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 and we’ll take a walk through its narrow streets – a great opportunity for our first Italian gelato! (Our hotel for the night is usually just outside of San Gimignano).

• Meals: Breakfast, lunch

Today we’ll start heading south, descending towards the plains of Colle Val d‘Elsa. We’ll ride past woodland and cultivated fields making our way towards the hill-top town of Casole d‘Elsa. The last four kilometres are challenging but the view from the top of the climb will hopefully outweigh the effort.

We should have some time to wander through this authentic medieval town, far away from the tourists and clichés of Tuscany.

We’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 us straight to our accommodation, in an ancient medieval village, surrounded by vast vineyards; an ideal place to taste the local wines. You’ve earned it!

• Meals: Breakfast, lunch

Today we face the most difficult stage of the week, with a climb through the Chianti region. Don’t worry though, it will be rewarded with great views and a glass of Chianti wine at the end of the day!

We’ll continue our ride past vineyards and dense oak forests towards Radda in Chianti, our home for the evening.

The village, famous for its wine, is located between the valleys of the rivers Pesa and Arbia on a forested hillside in the Chianti Classico region.

After settling into our accommodation, we’ll set off to a renowned ‘Enoteca’ where we have the opportunity to try some of the best of the Chianti wines produced in the region. With small boutiques and shops, Radda is the perfect place to pick up some local specialties.

• Meals: Breakfast, lunch, dinner

After breakfast we’ll set off for a stunning ride south past hills blanketed with vineyards and thick forests. This whole region is dotted with castles, once defensive systems but now privately owned by wine producers.

We ride past Meleto, San Donato in Perano and Brolio Castle, where we’ll stop for a morning coffee and a chance to look around.

Back on our bikes, we’ll continue our ride on the Lauretana route, once a paved Roman road filled with travellers, artists and pilgrims. We’ll ride through the spectacularly eroded clay badlands landscape, reaching Asciano, a walled city that has its origins in the founding of Rome.

The legend goes that the sons of Remus (Aschio and Senio) fled the newly founded city of Rome that their uncle Romulus ruled. Senio camped on the banks of the river Tresa, while Aschio settled on the left bank of the river Ombrone, founding new settlements, Asciano and Siena respectively.

• Meals: Breakfast, lunch

Today is our final day on the bikes with Siena our destination. We’ll ride a section of the “Eroica” route towards Castelnuovo Berardenga. Considered a marginal suburb of Siena, it’s actually a city full of charm, character and history.

After having a look around Castelnuovo Berardenga’s architecture and gardens, we’ll be on our way again, following a mix of tarmac and gravel roads as we get closer to Siena, with glimpses of bell towers and churches. Entering Siena from the Porta Romana will lead us straight to the heart of the city: Piazza del Campo where the famous Palio takes place. We deserve a toast with a glass of wine to celebrate the end of the tour in one of the elegant bars overlooking this vibrant square, (and since we’ve spent the week cycling through the Chianti region this may just be our tipple of choice)!

• Meals: Breakfast

Today we say ciao to this beautiful part of Italy and transfer back to Pisa airport for flights home. (Transfer approx. 2 hours)