Following arrival at Italy’s Pisa airport (PSA), you’ll make the 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
• Ascent: 925 Metres Approx.

Your self-guided Strade Bianche cycling experience starts 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 you begin with a gentle descent and within only a few kilometres of leaving Radda, you’ll join a section of the Strade Bianche of the Eroica which leads you on the start of your journey towards the picturesque Colli Senesi region.

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

On leaving Castelnuovo Berardenga this afternoon you’ll enter the heart of the Colli Senesi region, with a very panoramic Strada Bianca route which takes you along the ridgeline of the chalky hills before descending to Asciano, a typical Tuscany town set inside old, fortified walls.

• Meals: Breakfast
• Ascent: 1,080 Metres Approx.

You’ll start the day with a sweeping descent to the Arbia valley, firstly on tarmac then combining smooth Strade Bianche and small country roads as you 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 you back onto the hilltops.

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

• Meals: Breakfast
• Ascent: 1,325 Metres Approx.

This morning you can skip packing your bags and instead take your time to enjoy a relaxing breakfast as today’s loop ride will bring you back to San Quirico where you 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 you’ll be able to set a bit of time aside to explore the Roman remains and take pictures by the steaming pools.

Moving on, you’ll pick up a network of gravel roads that take you on a rolling ride through vineyards and cyprus trees. After crossing the Orcia river you can continue along the planned route to Pienza which takes you 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 you’ll continue your journey through the UNESCO protected landscape of Val d‘Orcia. Your return to San Quirico starts on some rougher gravel tracks before you rejoin another stretch of carefully managed Strada Bianca.

• Meals: Breakfast
• Ascent: 975 Metres Approx.

Today’s section of the Strade Bianche begins with a coffee stop in Montalcino, where you’ll have a little time to stroll around, visit the castle and perhaps buy a bottle or two of Montalcino Brunello to stash for later?

Leaving this stunning hill-top town, you’ll 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, you’ll 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. Your hotel is a short tarmac section away and a perfect ending to another great ride!

• Meals: Breakfast
• Ascent: 1,050 Metres Approx.

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

Leaving via the backroads, you’ll 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 you come out of a forested track, the imposing walled town of Monteriggioni will stand ahead of you on a hilltop. Following the winding road you’ll ride right up to the entrance gates where there is a choice of delicious gelato places to pick up your reward!

From Monteriggioni you’ll link onto the historic pilgrimage route of the via Francigena where a smooth gravel country road leads you to Colle Val d’Elsa and your accommodation.

• Meals: Breakfast
• Ascent: 615 Metres Approx.

Your final day in the saddle sees you riding through the hills of Val D‘Elsa and on mixed adventurous gravel terrain towards the picture perfect San Gimignano. As the view opens up revealing the ‘Town of Towers‘, you’ll no doubt be stopped in your tracks as you take in one of the prettiest and best preserved medieval settlements in Italy.

We’ve kept the millage today forgiving to give you plenty of time here to take a break from the bikes and walk around San Gimignano. Enjoy a coffee, climb one of the towers and end your trip in style with a scoop of the ice cream which often wins 1st prize at the world ice cream championships!

Leaving San Gimignano it’s just a few more kilometres to Pancole and your accommodation for the night.

• Meals: Breakfast

Time to say your farewells to Italy as after breakfast you’ll be taken back to Pisa airport (PSA) for your onward flights.