The freedom to cycle in Tuscany on your own
Tuscany is a dream for cyclists. Rolling hills, vineyards stretching to the horizon, and medieval towns full of charm. This trip gives you the freedom to explore the beauty of the region on your own, with bases in Florence, San Gimignano, and Siena. Plan your days as you wish - cycle, discover, and enjoy! Want to adjust the trip? The setup is flexible and can be adapted to your wishes.
Start your journey in Florence
The journey begins in Florence, the cultural capital of Tuscany. Here you can combine gentle cycling tours with visits to iconic places like Ponte Vecchio and the Uffizi. Explore the wine routes of the Chianti region and stop for wine tastings.
Cycle among cypresses in San Gimignano
In San Gimignano, known for its towers and picturesque landscapes, you can cycle through cypress avenues and visit historic villages like Volterra. Experience the Tuscan countryside up close and treat yourself to a glass of Vernaccia wine in the evening.
Siena - the heart of Tuscany and hills
The last part of the trip you spend in Siena. Explore the spectacular Crete Senesi landscape, cycle to the medieval village of Monteriggioni and finish with a tour in the Chianti region. Siena is a perfect place to combine active cycling with historical experiences, such as a visit to Piazza del Campo.
Plan your cycling trip with Sembo
This trip you do on your own. You can choose to drive down to Italy and bring your own bike, or fly to Florence and rent a bike on site. Florence Airport (Aeroporto di Firenze-Peretola) is the best option for flights. For those who want even more of Tuscany, Sembo offers booking of lovely excursions such as wine tastings, pasta courses and guided tours - perfect to complement your days in the saddle.
Flexibility for your trip
Do you want to change the trip or change the length of the stays? With this setup, you can easily adjust your bases and routes to suit your wishes. Add more days in Florence or Siena, or swap one destination for another Tuscan gem. It's your trip - make it exactly as you want!
Suggested Cycling Tours for This 9-Day Tuscany Bike Trip
Days 1–3: Florence – Cycling and Culture in the Heart of Tuscany
Accommodation: 3 nights outside Florence
Cycling Tours:
- Chianti Wine Route (Day 2): A ride to Greve in Chianti (approx. 50 km round trip), cycling through rolling hills and past scenic vineyards.
- Fiesole and the Arno River (Day 3): Explore the hills of Fiesole or take a leisurely ride along the Arno River (30–40 km).
Other Activities: Discover Florence’s rich culture with visits to the Uffizi Gallery, Florence Cathedral, and Ponte Vecchio.
Days 4–5: San Gimignano – Exploring Tuscany’s Medieval Gem
Accommodation: 2 nights in San Gimignano
Cycling Tours:
- Volterra (Day 4): A ride to Volterra (approx. 60 km round trip), known for its medieval architecture and stunning landscapes.
- Cypress Roads (Day 5): A shorter ride through olive groves and vineyards to charming villages like Certaldo (approx. 40 km).
Other Activities: Stroll through San Gimignano’s charming medieval center and taste the local Vernaccia wine.
Days 6–9: Siena – Cycling, History, and Tuscany’s Rolling Hills
Accommodation: 4 nights in Siena
Cycling Tours:
- Crete Senesi (Day 7): A scenic loop through the unique landscapes south of Siena (approx. 70 km).
- Monteriggioni (Day 8): Ride to the medieval walled village of Monteriggioni (approx. 50 km).
- Chianti Route (Day 9): Explore the Chianti region north of Siena (approx. 80 km), a perfect grand finale for your cycling adventure.
Other Activities: Visit Piazza del Campo and indulge in Siena’s rich culinary heritage.
A journey through Tuscany on two wheels—history, landscapes, and unforgettable flavors await!
A package tour and a linked arrangement offer travellers different booking processes but provide the same protection under the Package Travel Act, ensuring customer rights and peace of mind during the trip.
