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: 1,200 Metres Approx.

Our first day’s ride will take us from Casciana Terme to the gem of Tuscany, San Gimignano. Leaving our accommodation, 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: 1,030 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: 1,550 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: 1,270 Metres Approx.

In the morning we spend a little more time enjoying Pienza, located in the centre of the Val d‘Orcia. Pienza is often described as a ‘utopian city‘, representing 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.

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 next climb of the day will take us to the quintessentially Tuscan hilltop town of Montalcino, best known for its Brunello red wines. Here we stop for lunch, taking our time for a walk through the old town with its many osterie and wineshops.

In the afternoon, leaving the hill town, a long and gradual descent will take us back down towards Buonconvento and onto a gentle rollercoaster of superb riding through more countryside and farmland. The aim for today is the village of Vescovado near the hilltop hamlet of Murlo, where after settling in at our hotel we may well have a dip in the pool before sitting down for dinner.

• Meals: Breakfast, lunch
• Ascent: 1,765 Metres Approx.

From Vescovado today we head for the ancient Etruscan town of Volterra. Our route takes us north in direction of Siena to then veer west through the lesser known, but no less beautiful scenery of the Montagnola Senese hills. Here we cycle on small secondary roads between pastures, fields and old farm houses to Pievescola, Mensano and the enchanting medieval village of Casole d’Elsa, little known and well worth some time off the bike.

Eventually we will reach busy Volterra, one of Tuscany’s most evocative hill towns steeped in Etruscan, Roman and medieval history. After checking into our hotel and freshening up we can go out for a walk to explore the ancient remains, including the Etruscan gates and necropolis or the remains of the Roman forum and theatre. History and archaeology buffs may well pay a visit to the Museo Etrusco, one of Italy’s finest.

• Meals: Breakfast, lunch
• Ascent: 630 Metres Approx.

Our final day’s ride will take us back towards Casciana Terme. Taking a network of minor roads, we meander over rolling hills, stopping off in Lajatico, the home town of the famous Italian tenor Andrea Bocelli.

Arriving early in the afternoon in Casciana Terme will not only give us time to pack up our bikes without rushing, 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.