Home > Giro of Tuscany: Florence to Pisa via Siena
Savor 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 artistically inspired city of Florence, to the architectural wonders of Pisa.
You will pass by the famous road of wines, where a sip of the local Chianti or Brunello di Montalcino will help motivate you to continue on your journey. The local cuisine will surely quell your hunger, and the numerous pastoral 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.
Note that this cycling tour is ideal for who can comfortably cover 80 kilometers/50 miles on rolling hills.
For travel and cycling tips to Tuscany, visit our "travel and cycling tips" section.
Welcome to the capital of Tuscany! We hope you're excited! After all, you're about to be introduced to a plethora of new experiences in art, culture and delicacies. As you walk through Florence's cobblestone streets, immerse yourself in this old European city.
Take some time and admire its brick-laden walls, a familiar feature in Florence's architecture. Your bike tour will commence tomorrow, and as you prep yourself for your travels, you might want to wander around and see more of the local spots.
Drop by an art gallery or just enjoy the crowd in the plaza. There is a romantic atmosphere that sweeps through the city as the sun goes down.
From Florence, you'll be pedaling your way towards Impruneta, a city known for its terracotta art, quaint villas, and a famous basilica called the Sanctuary of Santa Maria.
Ten kilometers (6 miles) further and you will arrive at Mercatele, a little town surrounded by the hills of Chianti, also famous for its wineries. Indulge yourself in the local wine flavors and take a break stop at Greve's public square. You'll recognize it easily--it's a triangle!
Your destination for tonight is Radda in Chianti, where you can find the medieval palace of Pretorio as a landmark. Rest up tonight in your hotel, and get ready for your next ride.
Your next destination is Siena. From the hilly landscape of Chianti, you will be entering a quaint town with ancient forts. Spot Meleto's Castle, a true Tuscan villa perched by the countryside. Proceed through Castagnolli and take a break at the Castle of Brolio for a quick Ricasoli wine tasting.
With good pacing, you'll reach the city of Siena, known for being a UNESCO World Heritage Site. Don't miss Piazza del Campo where the Palio, Siena's famous horse race is held bi-annually.
Among your must-visits: 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 to get to the renowned Brunello vineyards. Don't stop yet--your wine-tasting session happens at Montalcino, just a few kilometers from the presses.
After a glass or two, you can start cycling your way to Asciano. Get your much-needed tranquil moment at Monte Oliveto Abbey, 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, more vineyards, and hidden villages that seem to hide from the dense forest.
Choose your route: explore more of the land's secrets by cycling the long option (108 km) or cut it short to a 70-km ride by taking a train from Montalcino to Siena.
Traveling along the Via Francigena, you'll get to visit small, busy villages before you reach Monteriggioni and its remarkable Roman abbey (Abbadia a Isola).
Gaze into the castle of Monteriggioni along the way and 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. From here, head to San Gimignano, where you'll experience a legitimate taste of a medieval city, a UNESCO world heritage site.
Next on the list is Volterra where you'll arrive in the late afternoon with enough time to enjoy artisan alabaster works and visit the Roman theatre, the Acropoli.
Enjoy the rest of the day strolling around the Romanesque centers as you settle down for the night.
Your last day of cycling is a less strenuous ride to the city of Pisa. Leave Volterra by the way of Ghizzano, a pleasant village surrounded by vineyards. Calcinaia, a small municipality, can be reached in two hours or so.
After reaching Pontedera, cycle along the Arno River all the way to Pisa, home of the world-famous Leaning Tower.
On the last day of your tour, you can wander around the city after breakfast.
Make sure you drop by Pisa's most favorite sites such as the Leaning Tower or the Piazza del Miracoli.
1 night in a 4-star hotel and 5 nights in 3-star hotels
6 nights in 4-star hotels