Home > Giro of Tuscany: Pisa to Florence via Siena
Savour your visit to the birthplace of the Italian Renaissance with our self-guided, “Giro of Tuscany” tour that includes some action-packed biking on some of the country's most beloved landscapes. Ride along mountain ranges and fertile plains as you pedal from city to city; starting off with the architectural wonders of Pisa and finishing in the artistically inspired city of Florence.
You’ll go along the famous “road of wines”, where a sip of the local Chianti or Brunello di Montalcino will help to motivate you on your way. The local cuisine will surely quell your hunger, and numerous magnificent views, full of well-preserved castles and cathedrals will feed your visual senses. In addition, the eager smiles of the locals will welcome you into their region!
For travel and cycling tips to Tuscany, visit our "travel and cycling tips" section.
Welcome to the world-renowned city of Pisa! The city is of course most well-known for its magical Piazza del Miracoli and its famous leaning tower. There is more to see in Pisa than just the Tower though; it is home to over 20 historical churches and numerous museums. Be sure to spend some time exploring this beautiful city, its wonderful architecture and experiencing its wealth of art and gastronomy as well! The cycling begins tomorrow so after a day of taking in the sights, enjoy a relaxing evening in your hotel ahead of your first day in the saddle.
Your first day’s ride begins by following the Arno River out of Pisa towards the town of Pontedera, home to the wine company Castellani and a sweets factory, called Amedei. From here you will ride through Ghizzano, a picturesque village set amongst vineyards. Enjoy this beautiful scenery as you continue on to Volterra, your home for the night. Volterra is a stunning, walled, medieval town set on a hilltop. Aim to arrive in the late afternoon with enough time to enjoy the artisan alabaster works and visit the Roman theatre, the Acropoli. Enjoy the rest of the day by strolling around the Romanesque centers before you settle down for the night.
Traveling along the Via Francigena, an ancient pilgrim route stretching from France to Rome and on to Apulia, you will reach the UNESCO world heritage site of San Gimignano. A hilltop hamlet, it is famous for its numerous towers. Next head on to visit Colle Val d'Elsa, dubbed as Italy's Bohemia. This area, named after an old Etruscan hero, is known for being a significant industrial center with medieval architecture. You will pass through several small, busy villages on your way to Monteriggioni and its remarkable Roman abbey (Abbadia a Isola). Soon after you will reach the city of Siena, another UNESCO World Heritage Site! Don't miss the Piazza del Campo where the Palio, Siena's famous horse race is held bi-annually. Among your must-sees: the Siena Cathedral, with its strong Gothic inspired architecture and Palazzo Publico, Siena's city hall.
Leaving the city center, you will be cycling through lush, green hills towards the renowned Brunello vineyards. Don't stop just yet--your wine-tasting is at Montalcino, just a few kilometers on from the presses. After a glass, or two, carry on to Asciano. Enjoy a deserved rest stop at Monte Oliveto Abbey, also known as the Crete Senesi--home of all things Tuscan. From where you stand, you will see a patchwork of fields with pillars of cypress trees, rolling hills, vineyards, and hidden villages that seem to hide in the dense forests. You can decide whether to continue exploring more of the land's secrets by riding the long option (115 km) or cutting it short and taking a train from Montalcino to Siena.
The first stop on today’s ride is Castagnolli, where you can admire Brolio Castle, home to the Ricasoli family and a well-managed wine cellar as well! Continue along the route, spotting Meleto Castle on the way, a beautiful Tuscan villa perched in the countryside on a hilltop. Today’s ride finishes in Radda in Chianti, a classic Chianti village nestled in the hills, among remnants of the Etruscan period. From here, you can see the Pretorio Palace, discover wine tours, and enjoy a leisurely stay at a nearby hotel.
Today you will discover Tuscany’s “Road of Wines” where the famous Chianti Classico wine is produced and home to the Chianti Classico Wine Festival held every September. The route leads you through beautiful Tuscan countryside into the town of Greve. Take a break in the main square, you will recognize it, it is a triangle! Head on to Mercatale, a small town offering a peek into the Chianti countryside and famed for its wine cellars. From here you will ride through Impruneta, a town filled with terracotta art! Florence awaits! The capital of Tuscany is famed for its wealth of culture, architecture, and art, and is considered the birthplace of the Renaissance. Take some time to admire its brick-laden walls, a familiar feature in Florence’s architecture. Perhaps drop by an art gallery visit some of the city’s main sites or just enjoy the crowd in the plaza. There is a romantic atmosphere that sweeps through the city as the sun goes down and you can reflect on an epic journey!
On the last day of your tour, you can wander around the city after breakfast and visit some of the sites you haven’t yet had a chance to see, before packing up your things and leaving Florence at your leisure.
6 nights in 3- and 4-star hotels