Following arrival at Pisa airport (PSA), we will transfer you to the charming town of Casciana Terme, a spa town retreat. You will receive your road book and we will provide you with all the information you will need for the duration of your trip, before we leave you to start your self-guided tour of Tuscany. Depending on your arrival time, 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.

Your first day’s ride will take you from Casciana Terme to the gem of Tuscany, San Gimignano. Leaving the hills around Pisa, the riding is gentle as you roller coaster along the roads of the ‘Colli Pisane‘, taking a network of minor roads past woodland, vineyards and small towns.

Just before you stop for your lunch you gradually climb through lush green woods, before the final descent towards San Gimignano. You will stop in your tracks as the view opens up, ahead of you the ‘Town of Towers’ and one of the prettiest and best preserved medieval settlements in Italy.

You should have plenty of time 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. A short ride will take you to your 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 your first day riding in Tuscany!

• Meals: Breakfast
• Ascent: 1,000 Metres Approx.

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

You will have time to ride up and through many of these small towns, absorbing the whole Tuscan experience. With incredible views, intimate piazzas and some wonderful boutiques and art galleries, these towns make a perfect itinerary for your bike ride. Your destination for today is Radda in Chianti.

Staying at the accommodation in the centre of Radda in Chianti, you have time to enjoy the atmosphere of this hill top town and indulge in some fine wine tasting and dining at some of the best restaurants of the region.

• Meals: Breakfast
• Ascent: 1,400 Metres Approx.

Today you leave Radda in Chianti and ride through Gaiole and on to Castelnuovo Berardenga, on your way to Pienza. Today’s ride takes you 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.

You will then ride past Meleto, San Donato in Perano and Brolio Castle. You can rest your legs in Asciano, yet another little medieval town set on a hillside, above the Ombrone Valley.

After a final roller coaster climb through the ‘Colli Sienesi‘, you will reach Pienza, your destination for today’s ride, the quintessential renaissance town in Tuscany.

• Meals: Breakfast
• Ascent: 900 Metres Approx.

Pienza is 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, you 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 the Italian landscape. You then 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. On to Castiglione d’Orcia with its picturesque stone paved streets and Romanesque church, the final climb of the day will take you to the quintessentially Tuscan hill town of Montalcino.

Narrow streets lined with boutiques, art shops and wine shops allows for a relaxing time. For wine lovers, Montalcino Brunello wines can be tasted in one of the many wine bars, savouring some of the best reds that the area has to offer.

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

You are getting to the end of your cycling in 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 you back down into Val d‘Orcia. Today’s riding will be a gentle roller coaster of superb riding through more countryside and farmland. Your destination for today is Casole d‘Elsa, a cobbled medieval town set on top of a hill, barely visited by tourists. Rewarded by the views and yet another gelato stop, you move in to your accommodation. After a dip in the pool you can then head back up to Casole for dinner at a traditional ‘osteria‘.

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

Your final day’s ride will take you back towards the rolling Pisan hills and Casciana Terme. Taking a network of minor roads, eventually ascending to Volterra, one of Tuscany’s most evocative hill towns. From the Etruscan gates to the remains of the Roman forum, you’ll capture the real Italian experience here. Arriving early afternoon in Casciana Terme, not only will it give you time to sort out your bikes but also to make the most of the hot springs and more fine dining and wine. A great way to end Italy’s ultimate riding experience.

It’s time for us to meet up with you again and transfer you back to Pisa airport for your flight home. (Transfer time approx 45 minutes).