Following arrival at Italy’s Pisa airport (PSA), we make the short transfer to the charming spa town of Casciana Terme, a quiet retreat where you can spend the rest of the day relaxing and enjoying the facilities.

Depending on flight arrivals, 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: 1,050 Metres Approx.

Our first day’s ride will take us from Casciana Terme to the gem of Tuscany, San Gimignano. Leaving the hills around Pisa, the riding is gentle as we roller-coaster along the roads of the ‘Colli Pisane‘, taking a network of minor roads past woodland, vineyards and small towns. Just before we stop for lunch we gradually climb through lush green woods, before reaching the small walled medieval hill-top town of San Gimignano.

This fascinating ‘town of towers’ is one of the prettiest and best preserved medieval settlements in Italy and we should have some time to walk around the square and taste the World Ice-Cream Championships 1st prize winning ice cream! The town is also known for its white wine Vernaccia di San Gimignano but we might save that for later!

A short ride later will take us to our delightful hotel, surrounded by vineyards and rolling hills. Depending on the time of year, a dip in the pool and relaxing with a drink, makes a great finish on our first day riding in Tuscany!

• Meals: Breakfast, lunch
• Ascent: 1,500 Metres Approx.

Leaving the charming town of San Gimignano, today’s ride is a roller-coaster through a picturesque landscape of little medieval fortified villages perched on top of hillsides, such as Castellina in Chianti and Radda in Chianti.

We have time to ride up and through many of these small towns, absorbing the whole Tuscan experience along the way. With incredible views, intimate piazzas and some wonderful boutiques and art galleries, these towns make a perfect passage for our journey. Our destination for today is Radda in Chianti.

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 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.

• Meals: Breakfast, lunch
• Ascent: 1,700 Metres Approx.

Today we leave Radda and ride to Gaiole in Chianti and on to Castelnuovo Berardenga, on our way to Pienza. Today’s ride takes us further 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. We will rest our legs in Asciano, yet another little medieval town set on a hillside, above the Ombrone Valley. After a final rollercoaster climb through the ‘Colli Sienesi‘, we reach the outskirts of Pienza, our destination for today’s ride, the quintessential renaissance town of Tuscany.

• Meals: Breakfast
• Ascent: 900 Metres Approx.

Being a short day, there is time to explore Pienza, a rare example of Renaissance town design. Often described as a ‘utopian city‘, it represents one of the best planned Renaissance towns, where a model of ideal living and government was attempted, based on the concept of a town able to satisfy the needs of a peaceful and hardworking populace. Pienza’s location in the centre of the Val d‘Orcia, a wonderful and untouched valley, helps the town to embody the fundamental principal that humanistic architecture attempted to incorporate – the balanced relationship between Man and Nature.

Leaving Pienza, we continue with a fantastic descent and a superb ride into the heart of Val d’Orcia, a UNESCO heritage region with conical hills lined by cypress trees, the ultimate aesthetic of Italian landscape. We ride on to San Quirico d’Orcia and Bagno Vignoni where legend has it that St Catherine and Pope Pius II both bathed in the thermal waters here. On to Castiglione d’Orcia with its picturesque stone paved streets and Romanesque church, the final climb of the day will take us to the quintessentially Tuscan hilltop town of Montalcino.

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

We are getting to the end of our tour of Tuscany and the riding is smooth along the rolling hills of the region around Montalcino. Leaving the hill town, a long and gradual descent will take us back down into Val d‘Orcia. Today’s riding will be a gentle rollercoaster of superb riding through more countryside and farmland. Our final destination for today is Strove – a very small hamlet not far from the medieval town of Monteriggioni.

• Meals: Breakfast, lunch
• Ascent: 1,350 Metres Approx.

Our final day’s ride will take us back towards Pisa and Casciana Terme. Taking a network of minor roads, we meander over rolling hills, stopping off in Casole d‘Elsa and eventually ascending into Volterra, one of Tuscany’s most evocative hill towns. From the Etruscan gates to the remains of the Roman forum, we’ll capture the real Italian experience here. Arriving early afternoon in Casciana Terme, will not only give us time to pack up our bikes but also to make the most of the hot springs, indulging in thermal baths and more fine dining and wine. A great way to end Italy’s ultimate riding experience.

• Meals: Breakfast

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