Scenic Tuscany Cycling in Charming Hotels
Immerse yourself in the laidback tuscan lifestyle
Lifetime Deposit
Self-Guided
Scenic Tuscany Cycling in Charming Hotels Overview
This cycling tour through Tuscany offers an unforgettable journey through Italy's most picturesque landscapes. Pedal along quiet roads and scenic paths that wind past cypress-lined avenues, golden wheat fields, and world-renowned vineyards. The route takes you to historic towns like Florence, Siena, Montepulciano, and Montalcino, rich in art, culture, and medieval charm. Along the way, you'll experience Tuscany's culinary delights, including traditional pasta dishes and local olive oils, while enjoying exquisite wines from the famous Brunello di Montalcino and Chianti regions. With a mix of gently rolling hills and more challenging climbs, this tour offers both breathtaking views and an immersive cultural experience in the heart of Italy's wine country.
Trip highlights
Pedal past cypress-lined avenues, rolling hills, and golden wheat fields, with breathtaking views of Tuscany’s renowned vineyards and picturesque countryside.
Explore historic towns like Florence, Siena, Montepulciano, and Montalcino, each offering rich art, architecture, and medieval charm.
Ride through the world-famous wine regions of Brunello di Montalcino and Chianti, with opportunities to sample exquisite local wines.
Savor traditional Tuscan cuisine and specialties, from hearty pasta dishes to the finest local olive oils and cheeses, all complemented by panoramic vineyard views.
Day By Day Itinerary
Stroll through the charming city and marvel at world-renowned art history.
- Overnight Location:
- Hotel in Florence
- Distance:
- None
- Meals:
- None
After a morning train ride to Arezzo, enjoy a brief stroll through the old town before cycling through the scenic Val di Chiana valley. Pass through olive groves and gentle hills before reaching Lake Trasimeno and the historic town of Passignano.
- Overnight Location:
- Hotel in Passignano sul Trasimeno
- Distance:
- 62 km + train ride, 330 m of ascent, 330 m of descent
- Meals:
- Breakfast
Cycle along the lakeshore to Castiglione, where you’ll have stunning views of Lake Trasimeno. Ride into the rolling hills of Tuscany, passing renowned vineyards before reaching the hilltop town of Montepulciano.
- Overnight Location:
- Hotel in Montepulciano
- Distance:
- 53 km, 500m of ascent, 220 m of descent
- Meals:
- Breakfast
Travel along cypress-lined roads to Montechiello and follow the Strade Bianche to Pienza. The picturesque Val d’Orcia will guide you to Montalcino, known for crafting the famous Brunello wine.
- Overnight Location:
- Hotel in Montalcino
- Distance:
- 50 km, 1070 m of ascent, 1140 m of descent
- Meals:
- Breakfast
Ride through golden wheat fields on the “Eroica” route, surrounded by captivating landscapes and historic estates. In Siena, explore the famous Piazza del Campo and admire the towering Palazzo Pubblico.
- Overnight Location:
- Hotel in Siena
- Distance:
- 58 km, 680 m of ascent, 890 m of descent
- Meals:
- Breakfast
Cycle along scenic mountain roads with vineyard views. Pause in Vagliali for a cappuccino and follow white gravel roads through vineyards to Radda. Explore Castellina and the heart of Chianti for an authentic experience.
- Overnight Location:
- Hotel in Radda
- Distance:
- 22/67 km, 520/1140 m of ascent, 330/960 m of descent
- Meals:
- Breakfast
Continue past vineyards and olive groves, cycling through Greve in Chianti. The journey concludes with a descent to Florence, where you can savor the last of Tuscany's delights.
- Overnight Location:
- Hotel in Florence
- Distance:
- 59 km, 820 m of ascent, 1270 m of descent
- Meals:
- Breakfast
End your tour with individual departure or extend your trip with further cycling adventures.
- Overnight Location:
- None
- Distance:
- None
- Meals:
- Breakfast
Tour Map
We know Adventure
10Adventures only does Hiking, Cycling and Adventure Holidays. Its our mission to help you explore the world!
Inclusions
Included
- 7 breakfasts are included.
- Accommodations for 7 nights are included.
- Transportation for your luggage is included throughout the tour, however, you will be cycling from town to town yourself.
- Detailed Digital travel information documents
- App for Navigation and GPS-data
- Service hotline
- Welcome briefing
- 1 train ride Florence – Arezzo including bike transport
Not included
- Any personal transfers
- Local tourist tax
- Guide
- Bike rental
Optional Extras
- Extra nights in accommodations
- Printed Route Book
- Bike rental:
- Hybrid Bike
- E-Bike
Reviews
These reviews reflect all trips offered by this local tour partner on 10Adventures, not just the tour you’re viewing.
These reviews reflect all trips offered by this local tour partner on 10Adventures, not just the tour you’re viewing.
Travellers love 10Adventures
View all
FAQ
We rate the difficulty of this tour as a 5 / 5. Expect a hilly terrain and several steep climbs starting from the second stage. While most of the route follows low-traffic secondary roads and well-maintained gravel paths, cyclists should be prepared for heavier traffic near cities. A solid level of fitness is required to comfortably navigate the daily climbs and extended distances.
Check with your local country about visa requirements. You could also try this website, though you should verify with your government.
7 breakfasts are included.
Yes, it is mandatory to have health and medical insurance to join this trip, and your insurance should cover cycling. Get your travel insurance.
Florence's Amerigo Vespucci Airport (FLR) offers direct flights from several European cities. From the airport, it's about a 20-minute drive or taxi ride to the city center, or you can take a bus shuttle to the central train station, Santa Maria Novella.
The tour ends where it starts, in Florence.
Check with your family doctor.
Please check with your local government about travel restrictions before you book your tour. This map from the US Department of State provides an overview of the current status in countries around the globe. The UK‘s Foreign Office and Government of Canada also provide advice on foreign travel. Note that the travel advice may change depending on your nationality.
Why book Scenic Tuscany Cycling in Charming Hotels with 10 Adventures?
Self-guided Specialists
Combine the freedom of travelling on your own with the confidence that all of the logistics are taken care of.
Packed with Inclusions
Accommodations, luggage transfers, gear rentals, and more - all taken care of so you can focus on making memories.
World Class Support
Have peace of mind for when travel plans change with our hassle-free booking process and unbeatable support.
Let's start talking about your next adventure!