Self-guided Tuscany Bike Tour

Your journey begins in Florence, the cradle of the Renaissance, where art and history greet you at every corner.

Florence is the birthplace of some of the most famous artists, painters, and writers known to humanity. From Dante Alighieri of the Divine Comedy, to Leonardo da Vinci to Michelangelo, to Florence Nightingale, all were natives of Florence.

Our hotel in Florence is a heritage property dating back to the 18th century that was the residence of a local nobel family till 1956. It is located in the heart of the historic centre of Florence.

After checking into your hotel, take time to explore the city's iconic landmarks. Stroll through Piazza della Signoria, admire the sculptures outside the Uffizi Gallery, and cross the Ponte Vecchio, lined with its traditional goldsmith shops. A visit to Palazzo Pitti and the beautiful Boboli Gardens offers a glimpse of Florence’s aristocratic past.

In the evening, enjoy a welcome dinner in a traditional trattoria, savoring Florentine steak or handmade pici pasta paired with a local Chianti wine.

Your cycling adventure begins as you leave Florence behind and pedal into the rolling hills of Chianti, one of Italy’s most renowned wine regions.

The ride takes you through a patchwork of vineyards, olive groves, and cypress-lined roads, with opportunities to stop at Palagio Castle for a wine tasting.

The day ends in Greve in Chianti, a lively village with a charming main square, home to local markets, wine shops, and artisanal stores. Unwind with a glass of Chianti Classico, produced from the Sangiovese grape, before settling in for the night.

Elevation: +700 m. / - 530 m.

Today’s route follows the famous Strada del Vino (Wine Road), winding through historic vineyards and medieval villages. This is the oldest wine growing region of Chianti, and the prized Chianti Classico wines come from this region in the heart of Tuscany.

Pass through Panzano, a small town known for its artisan butchers and exceptional wines, before reaching Radda in Chianti, a medieval village perched on a hilltop.

The town’s stone streets, fortified walls, and scenic views over the vineyards make it a perfect place to relax and soak in the charm of Tuscany.

Take the afternoon to enjoy a wine tasting at a historic estate, or visit the Casa del Chianti Classico, a museum dedicated to the region’s winemaking traditions.

Our hotel for the night is located in a historic building dating back to the 15th century. They serve the finest Chianti wines, so make sure to try some.

Elevation: +710 m. / - 430 m.

Cycle deeper into Chianti Classico territory, passing by historic wine estates and legendary castles like Castello di Brolio, home to the Ricasoli family, pioneers of the Chianti wine formula.

We recommend stopping for a wine tasting at Meleto Castle before continuing to Siena, a city that feels like stepping into the Middle Ages.

A highlight of Siena is the Piazza del Campo, a UNESCO World Heritage Site famous for the Palio horse race, and perhaps, one of the most spectacular town squares in the world.

Wander through narrow alleys lined with Gothic buildings, visit the stunning Siena Cathedral, and end your day with a leisurely dinner of pici pasta and wild boar ragu.

Elevation: +690 m. / - 870 m

Start the morning with a final stroll through Siena’s atmospheric streets before heading towards Monteriggioni, a perfectly preserved medieval fortress town surrounded by high stone walls and 14 watchtowers.

Dating back to the 12th century AD, the turrets of Monteriggioni were immortalized by Dante Alighieri in his classic The Divine Comedy by comparing them to a ring of giants.

This gentle cycling stage follows part of the Via Francigena, an ancient pilgrimage route leading to Rome that is considered one of the three most sacred pilgrimages in Christendom, along with the Camino de Santiago and Jerusalem.

The ride ends in Colle Val d’Elsa, a town known for its fine crystal glass production. Explore its historic center, visit a local glass-blowing workshop, or simply relax in this charming Tuscan village.

Elevation: +220 m. / -420 m

A highlight of the tour, today’s ride takes you to San Gimignano, a UNESCO World Heritage Site famous for its skyline of medieval towers. Once a powerful trading hub, San Gimignano is now a beautifully preserved medieval village, known for its Vernaccia wine, saffron, and gelato.

After exploring the town, the ride continues with a challenging climb to Volterra, an ancient Etruscan and Roman city. The reward is breathtaking views and a chance to explore Volterra’s Roman amphitheater, Etruscan walls, and alabaster workshops.

Stay for the night is in a charming hotel whose history dates back to 1482 AD when it used to be a convent for cloistered sisters or catholic nuns who lived a life remote from society.

Elevation: +1020 m. / -630 m.

Your final ride begins with a long descent through the rolling Tuscan countryside, passing small villages and olive groves.

The landscape flattens as you approach Pontedera, the birthplace of the iconic Vespa scooter.

If time allows, visit the Vespa Museum before taking a short train transfer to Pisa (not included).

Celebrate the end of your cycling adventure with a farewell dinner, perhaps indulging in some fresh seafood and a glass of Tuscan white wine.

Elevation: +170 m. / -700 m.

Take the morning to explore Pisa’s charming historic center, with its riverfront palaces, lively piazzas, and local markets. Visit the famous Piazza dei Miracoli, home to the Leaning Tower of Pisa, considered one of the original seven wonders of the world.

Pisa was also the birthplace of Galileo, perhaps the greatest astronomer of all time.

If time allows, enjoy a coffee in Piazza delle Vettovaglie before checking out of your hotel. From here, you can return to Florence by train or continue exploring Italy on your own.