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Highlights
Immerse yourself in the laidback tuscan lifestyle
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.
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.
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.
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Scenic Tuscany Cycling in Charming Hotels Tour Itinerary
Day 1 Arrival in Florence
Stroll through the charming city and marvel at world-renowned art history.
Overnight Location: Hotel in Florence
Distance: None
Meals: None
Day 2 Florence to Passignano sul Trasimeno
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: 60 km
Meals: Breakfast
Day 3 Passignano sul Trasimeno Montepulciano
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: 50 km
Meals: Breakfast
Day 4 Montepulciano to Montalcino
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
Meals: Breakfast
Day 5 Montalcino to Siena
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: 55 km
Meals: Breakfast
Day 6 Siena to Radda in Chianti
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: 30/70 km
Meals: Breakfast
Day 7 Radda to Chianti to Florence
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: 55 km
Meals: Breakfast
Day 8 Departure or Extension
End your tour with individual departure or extend your trip with further cycling adventures.
Overnight Location: None
Distance: None
Meals: Breakfast
Scenic Tuscany Cycling in Charming Hotels Tour Price and Dates
This self-guided tour is always run as a private tour for your group only, where the pricing depends on your travelling dates, as well as the types of rooms that you need.2025 Departures: The departures are available every Saturday from April 4th to October 10th, 2025.
- Single room: from EUR2048*
- Sharing a double room: from EUR1389*
Accommodation on Scenic Tuscany Cycling in Charming Hotels Tour
This tour offers charming and comfortable accommodations, ranging from historic palazzos and lakeside hotels to elegant spa resorts, all carefully selected to provide relaxation and a touch of local character after a day of cycling. In some cases, the accommodation listed below may need to be substituted for other comparable accommodations.
Single Rooms and Solo Travellers
Rooms are double occupancy. You can pay a supplement to have a private room in a hotel where possible. Solo travellers may be required to pay a supplement.
What’s Included in the Scenic Tuscany Cycling in Charming Hotels Tour?
Meals
7 breakfasts are included.
Accommodations
Accommodations for 7 nights are included.
Transportation during the Tour
Transportation for your luggage is included throughout the tour, however, you will be cycling from town to town yourself.
Also Included
- Detailed travel documents 1x per room (German, English, French)
- 1 Majorcan lunch snack in Petra
- App for Navigation and GPS-data
- Service hotline
Not included
- Any personal transfers
- Local tourist tax
- Guide
- Bike rental
Optional Extras
- Extra nights in accommodations
- Bike rental:
-
- Standard bike
- Upgraded standard bike
- Gravel bike
- E-Bike
- How hard is the Scenic Tuscany Cycling in Charming Hotels Tour?
- Do I need a visa to travel to Italy?
- Are meals included on the Scenic Tuscany Cycling in Charming Hotels Tour?
- Do I need insurance?
- How do I get to Florence to start this tour?
- Where does the Scenic Tuscany Cycling in Charming Hotels Tour end?
- Do I need special vaccines to travel to Italy?
- Are there any travel restrictions for Italy?
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.
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