Home > Giro of Tuscany: Pisa to Florence via Siena

Giro of Tuscany: Pisa to Florence via Siena

Rouler sur des routes sécondaires à travers la Toscane 5
Link towns cycling on quiet roads in Tuscany This tour ends in Florence with its beautiful Canal The itinerary takes you to Tuscan countryside with its beautiful villages Take advantage to share you cycling exprerience in the surrounding nature and beauty Ride the hills and valleys in Tuscany from Pisa to Florence via Siena
Rouler sur des routes sécondaires à travers la Toscane

Giro of Tuscany: Pisa to Florence via Siena

  • Level
  • PriceFrom 805 euros
  • DAY6 nights / 7 days

More info: Receive detailed hotel list, bike specs, and route description

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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.


D1Saturday: Arrival in Pisa


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.

D2Sunday: Pisa – Volterra Mileage: 78 km / 48 miles; Total Climb: 910 m / 2,986 ft; Total Descent: 380 m / 1,247 ft


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.


D3Monday: Volterra – Siena Mileage: 67 km / 42 miles; Total Climb: 1,040 m / 3,412 ft; Total Descent: 1,220 m / 4,003 ft


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.

D4Tuesday: Siena — Montalcino — Siena Short Option: Mileage: 85 km / 53 miles; Total Climb: 850 m / 2,789 ft; Total Descent: 850 m / 2,789 ft; Long Option: Mileage: 124 km / 77 miles; Total Climb: 1,810 m / 5,938 ft; Total Descent: 1,810 m / 5,938 ft


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.


D5Wednesday: Siena – Radda in Chianti Mileage: 44 km / 27 miles; Total Climb: 880 m / 2,887 ft; Total Descent: 670 m / 2,198 ft


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.


D6Thursday: Radda in Chianti – Florence Mileage: 79 km / 49 miles; Total Climb: 1,230 m / 4,035 ft; Total Descent: 1,700 m / 5,577 ft


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!

D7Friday: Departure


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.  

Booking & Prices

  • Price Details
  • 6 nights in 3- and 4-star hotels

  • 805 euros per person in March, April and October. Single supplement is 230 euros
  • 930 euros per person in May, June and September. Single supplement is 240 euros
  • 955 euros per person in July and August. Single supplement is 250 euros

These prices include:

  • 6 nights' accommodation 
  • Daily breakfast
  • Meeting with our local representative
  • Luggage transfers
  • Marked maps and/or cue sheets and route notes
  • Tourist information
  • Assistance if necessary (you will be provided with our local rep's mobile number)
  • Service charges and most taxes

These prices do not include:

  • Nominal city taxes, to be paid in cash directly at each hotel (total of approx. 15-17 euros).
  • Expenses of a personal nature
  • Travel insurance
  • Bicycle rentals. Full-carbon bikes are available at the rate of 190 euros per bike (this price includes the drop-off fee for the bike's return to Florence).

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