Immerse yourself in the laidback tuscan lifestyle
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.
Highlights of the Scenic Tuscany Cycling in Charming Hotels
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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 $2,225 USD*
- Sharing a double room: from $1,525 USD*
*-Pricing for this tour depends on the dates of your trip. Please click the booking button below to get the exact pricing for your trip dates. The prices listed are per person.
Book NowAccommodation 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.
Hotels on Standard Tour
C-Hotels in Florence ★★★★
Located in the heart of Florence, C-Hotels offer modern comfort and convenience, situated just steps from the Santa Maria Novella railway station.
Hotel Lido in Passignano sul Trasimeno ★★★
Hotel Lido in Passignano sul Trasimeno is a comfortable lakeside hotel offering stunning views of Lake Trasimeno, with modern amenities and easy access to the historic town center, making it a perfect base for exploring the beautiful Umbria region.
Palazzo Mosela in Montepulciano ★★★
Set within the historic center of Montepulciano, Palazzo Mosela is a distinguished building near the ancient Porta al Prato, offering a charming medieval ambiance.
Drogheria & Locanda Franci in Montalcino
This boutique hotel blends Tuscan tradition with modern comfort, offering a warm and discreet atmosphere just steps from Montalcino’s historic core.
Hotel Garden in Siena ★★★★
Surrounded by a majestic eighteenth-century park, Hotel Garden is a serene retreat located just outside Siena’s city walls, featuring lush rose gardens and tranquil surroundings.
Relais & Spa Vignale in Radda in Chianti ★★★★
Relais & Spa Vignale offers elegant accommodations with a historic flair, complemented by a relaxing spa and panoramic views of the Chianti hills from its stunning pool.
C-Hotels in Florence ★★★★
Located in the heart of Florence, C-Hotels offer modern comfort and convenience, situated just steps from the Santa Maria Novella railway station.
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:
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- Standard bike
- Upgraded standard bike
- Gravel bike
- E-Bike
Frequently Asked Questions about Scenic Tuscany Cycling in Charming Hotels
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