Tuscany: Siena, Chianti & Val d'Orcia

The City of the Palio.

Arrive in Siena, one of Europe's most beautifully preserved medieval cities, and settle into your hotel. Spend the afternoon exploring its atmospheric streets, hidden lanes and grand historic squares at your own pace.

Visit the magnificent Siena Cathedral (Duomo) , renowned for its extraordinary marble inlaid floor and richly decorated interior, before making your way to the iconic Piazza del Campo. This distinctive shell-shaped square lies at the heart of the city and is famous as the setting for the Palio di Siena, the thrilling historic horse race held here twice each summer.

Take time to enjoy a coffee or aperitivo in the piazza and soak up the unmistakable atmosphere of this remarkable Tuscan city before your cycling adventure begins.

Overnight: Siena

The Crete Senesi and Chianti.


Elevation: Ascents of up to 830m.

Leave Siena behind and enter the spectacular Crete Senesi, the distinctive landscape of southern Tuscany known for its rolling clay hills, sweeping fields and solitary cypress trees. The scenery becomes increasingly open and dramatic as you ride through this quintessential Tuscan countryside.

Continue towards Castelnuovo Berardenga, a historic town dating back to 1366 and marking the southern edge of the celebrated Chianti wine region. Take time to explore some of the area's architectural treasures, including the Romanesque Pieve di Pacina, before continuing to the beautifully preserved medieval village of San Gusmè.

From here, continue through the peaceful Tuscan hills to Asciano, your overnight destination and an ideal base from which to appreciate the unique beauty of the Crete Senesi.

Overnight: Asciano

Abbeys and Renaissance Jewels.

Continue deeper into the breathtaking landscapes of southern Tuscany, riding through the rolling hills of the Val d'Orcia towards the magnificent Abbey of Monte Oliveto Maggiore. Hidden among cypress trees and dense woodland, this historic Benedictine monastery is renowned for its peaceful setting, elegant architecture and remarkable Renaissance frescoes depicting the life of St Benedict.

After exploring the abbey, continue through the UNESCO-listed Val d'Orcia, where vineyards, wheat fields and cypress-lined ridges create some of Tuscany's most iconic scenery.

Your destination is Pienza, an exquisite little Renaissance town perched above the valley. Often described as an ideal Renaissance city, Pienza is home to a beautiful Duomo, fascinating museums and elegant palazzi. Take time to wander its atmospheric streets and enjoy spectacular views across the surrounding countryside.

Overnight: Pienza

The Land of Brunello.

Leave Pienza behind and follow a spectacular strada bianca—one of Tuscany's iconic white gravel roads—through the rolling landscapes of the Val d'Orcia. The route leads to the medieval walled town of San Quirico d'Orcia, where you can pause to admire the impressive 12th-century Collegiate Church and its beautifully preserved Romanesque façade.

From here, prepare for a rewarding climb towards Montalcino, perched high above the surrounding vineyards and renowned as the home of Brunello di Montalcino, one of Italy's most prestigious wines. Take time to explore the town's historic centre, visit the imposing 14th-century fortress and discover the local history at the Civic and Diocesan Museum.

After soaking up the views—and perhaps sampling a glass of Brunello—leave Montalcino behind on a beautiful descent through the Tuscan hills to Murlo, a tiny and atmospheric hilltop village surrounded by peaceful countryside.

Overnight: Murlo

Watchtowers and Cobbled Streets.

 Elevation: Ascent of up to 680 m.

Leave Murlo behind and ride through the peaceful countryside surrounding Siena, alternating between shady woodlands, open farmland and rolling hills with wide-ranging views across the Tuscan landscape.

Your route leads to the remarkable medieval village of Monteriggioni, a tiny fortified settlement built in the 13th century. Encircled by imposing stone walls and crowned by 14 perfectly preserved towers, Monteriggioni is one of Tuscany's most evocative medieval landmarks. Take time to wander its quiet central square and explore the historic ramparts.

Continue through the countryside to Colle Val d'Elsa, a historic town famed for its long tradition of glass and crystal production. This evening, explore the atmospheric upper town, where cobbled lanes, stone buildings and quiet piazzas reveal centuries of Tuscan history.

Overnight: Colle Val d'Elsa

Etruscan History and Alabaster.


Elevation: Ascents of up to 1,110 m.

Today brings one of the more challenging and rewarding stages of the journey. Cross the valley and climb over two scenic ridgelines, with increasingly expansive views across the Tuscan countryside, before reaching the spectacular hilltop city of Volterra.

Perched high above the surrounding valleys, Volterra has a history stretching back to the Etruscans, and its ancient stone walls and gateways still form part of the city today. Spend the afternoon exploring its atmospheric medieval streets and discovering traces of its remarkable past, including Etruscan remains, ancient tombs and Roman ruins.

Don't miss the Etruscan Museum, the cathedral and local art collections, or the traditional alabaster workshops for which Volterra has been famous for centuries.

With its dramatic setting, layered history and beautifully preserved historic centre, Volterra is one of Tuscany's most fascinating hill towns.

Overnight: Volterra

The Medieval Skyline.

Leave Volterra behind and cycle through peaceful forests and rolling hills, passing through a remarkably well-preserved medieval landscape of vineyards, olive groves and quiet country roads.

Your reward is San Gimignano, one of Tuscany's most iconic hill towns. Encircled by medieval walls and instantly recognisable by its celebrated stone towers, the town's distinctive skyline rises dramatically above the surrounding countryside.

Take time to explore its atmospheric streets and historic piazzas, and visit the richly decorated Collegiata, the Palazzo del Popolo and the beautiful church of Sant'Agostino.

Continue cycling to Certaldo, a charming medieval hill town with a fascinating historic centre. From here, take the train back to Siena, bringing your Tuscan cycling adventure full circle.

Train ticket from Certaldo to Siena is not included.

Tour Ends: Siena