Following arrival at Italy’s Pisa airport (PSA), we make the short transfer to the charming town of Radda in Chianti.

Depending on flight arrival times, there should also be time to have a quick leg stretch on your bikes before your evening meal in one of the town’s great restaurants.

• Meals: Breakfast, lunch
• Ascent: 675 Metres Approx.

We have chosen to start our Tuscany Gravel journey right in the heart of the Chianti region, and more precisely right on the classic Eroica route.

Radda in Chianti’s hilltop position affords a forgiving start to the day as we begin with a gentle descent and within only a few kilometres of leaving Radda we join a section of the Strade Bianche of the Eroica which leads us on the start of our journey towards the picturesque Colline Sienesi region.

It’s not long before the undulating hills of the wine-growing region start to kick in and we begin to get accustomed to the rolling countryside that will characterise our week’s riding. The rest of the day’s ride sees smooth gravel routes taking us through dense forests and past Chianti vineyards, and views of old Tuscan castles scattered on the hill tops.

On leaving Castelnuovo Berardenga this afternoon we enter the Colline Sienesi region, with a very panoramic Strada Bianca route which takes us along the ridgeline of the chalky hills before descending to Asciano, a typical Tuscany town set inside old, fortified walls.

• Meals: Breakfast
• Ascent: 855 Metres Approx.

We start the day with a sweeping descent to the Arbia valley, firstly on tarmac then combining smooth Strade Bianche and small country roads as we follow the Arbia river to Buonconvento. The Piazza Centrale, close to the walled monastery is the perfect place for a morning coffee stop ahead of the next section of climbing to take us back onto the hilltops.

Our climb out of Buonconvento is rewarded with some fantastic riding along remote tracks in the chalky hills. Back on the Eroica route, we pedal surrounded by 360 degrees of stunning Tuscan landscape of hills lined with cypress trees before finally reaching our destination in San Quirico d’Orcia where will stay for the next two nights.

• Meals: Breakfast, lunch
• Ascent: 1,180 Metres Approx.

This morning we can skip packing our bags and instead take our time to enjoy a relaxing breakfast as today’s loop ride will bring us back to San Quirico where we will stay another night. The riding options from this well-positioned town are numerous but all will start with a ride to the well-known hot springs of Bagno Vignoni where we set a bit of time aside to explore the roman remains and take pictures by the steaming pools.

Moving on, we pick up a network of gravel roads that take us on a rolling ride through vineyards and cyprus trees. After crossing the Orcia river we can continue along the planned route to Pienza which takes us along some classic white gravel roads, or those who would prefer a few more miles can opt for some smoother tarmac and take the longer, hillier route via Monticchiello.

From the stunning Pienza, and suitably refuelled from the obligatory coffee stop we continue our journey through the UNESCO protected landscape of Val d‘Orcia. Our return to San Quirico starts on some rougher gravel tracks before we rejoin another stretch of carefully managed Strada Bianca.

• Meals: Breakfast
• Ascent: 950 Metres Approx.

Another day of riding and a few more adventurous trails this afternoon! Our first coffee stop is in Montalcino, where we’ll have a little time to stroll around, visit the castle and perhaps buy a bottle or two of Montalcino Brunello to stash in the support van for later?

Leaving this stunning hill-top town, we ride on another classic section of Strada Bianca through woodland towards Castiglion del Bosco and on to Bibbiano. Adding a bit of adventure on a narrower track, we follow an old mining trail leading us to Murlo, a very small village where another stop is required at the only café which is run by two old ladies and is the epitome of Italian hospitality. Our hotel is a short tarmac section away and a perfect ending to another great ride!

• Meals: Breakfast, lunch
• Ascent: 970 Metres Approx.

A smooth but rolling Strada Bianca will lead us today to the outskirts of Siena, where we will switch onto a final stretch of tarmac to ride into this lively and bustling city. Stopping in Piazza del Campo for a coffee, we set some time aside to stroll to the imposing Duomo and take in the atmosphere of the stunning provincial capital.

Leaving via the backroads, we head towards the “Montagnola” a forested hill to the northwest of Siena. The riding is more adventurous on more uneven terrain, mixing some forest tracks with gravel country roads. As we come out of a forested track, the imposing walled town of Monteriggioni will stand ahead of us on a hilltop. Following the winding road we ride right up to the entrance gates where there is a choice of delicious gelato places to pick up our reward!

From Monteriggioni we link onto the historic pilgrimage route of the via Francigena where a smooth gravel country road leads us to Val d’elsa and our accommodation.

• Meals: Breakfast
• Ascent: 1,300 Metres Approx.

Our final day in the saddle sees us riding through the hills of Val D’Elsa towards the picture perfect San Gimignano. As the view opens up revealing the ‘Town of Towers‘, we’ll no doubt be stopped in our tracks as we take in one of the prettiest and best preserved medieval settlements in Italy.

We should have plenty of time here to take a break from the bikes to walk around San Gimignano, climb one of the towers and taste the ice cream which won 1st prize at the world ice cream championships!

Leaving San Gimignano we’ll head on towards our home for the evening in Volterra.

• Meals: Breakfast

Time to say our farewells as after breakfast we will take you back to Pisa airport (PSA) for your onward flights.