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Highlights
Cycle Tuscany’s Val d’Orcia, enjoy local wine, scenic routes & relaxed stays.
Ride through Tuscany’s stunning landscapes, medieval villages, and rolling hills, with stops for wine and local delicacies.
Taste world-famous Brunello di Montalcino, Vino Nobile, Pecorino cheese, and traditional Tuscan cuisine along your journey.
Explore charming towns like Cortona, Montepulciano, Pienza, and Siena, each rich in history, culture, and breathtaking views.
Pedal scenic roads past vineyards, olive groves, and cypress-lined paths, with flexible route options for all levels.
Experience the Cortona to Siena Cycling Tour, a breathtaking self-guided bike tour through the heart of Tuscany. Ride past rolling vineyards, medieval villages, and stunning landscapes, including the UNESCO-listed Val d'Orcia. This cycling holiday offers the perfect balance of exploration and relaxation, with multiple two-night stays to immerse yourself in Italy’s rich history, culture, and cuisine.
Pedal through charming hilltop towns like Cortona, Montepulciano, Pienza, and Montalcino, discovering their Renaissance architecture, local wineries, and artisan shops. Savor Brunello di Montalcino, Vino Nobile, and traditional Tuscan dishes as you cycle through iconic landscapes. From the shores of Lake Trasimeno to the medieval streets of Siena, each day offers scenic rides, historical landmarks, and unforgettable experiences. Whether you're cycling past cypress-lined roads, historic abbeys, or picturesque farmhouses, this Tuscany bike tour is an unforgettable way to explore one of Italy’s most spectacular regions.
Experience the Cortona to Siena Cycling Tour, a breathtaking self-guided bike tour through the heart of Tuscany. Ride past rolling vineyards, medieval villages, and stunning landscapes, including the UNESCO-listed Val d'Orcia. This cycling holiday offers the perfect balance of exploration and relaxation, with multiple two-night stays to immerse yourself in Italy’s rich history, culture, and cuisine.
Pedal through charming hilltop towns like Cortona, Montepulciano, Pienza, and Montalcino, discovering their Renaissance architecture, local wineries, and artisan shops. Savor Brunello di Montalcino, Vino Nobile, and traditional Tuscan dishes as you cycle through iconic landscapes. From the shores of Lake Trasimeno to the medieval streets of Siena, each day offers scenic rides, historical landmarks, and unforgettable experiences. Whether you're cycling past cypress-lined roads, historic abbeys, or picturesque farmhouses, this Tuscany bike tour is an unforgettable way to explore one of Italy’s most spectacular regions.
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Cortona to Siena Cycling Tour Itinerary
Day 1 Arrival in Cortona
Welcome to the stunning hill town of Cortona, perched above the Chiana River Valley. Famous for its delicious Chianina steak, this medieval town dates back to 600 BC, offering a perfect introduction to Tuscany. Take time to explore the Etruscan Museum or admire Fra Angelico’s paintings at the Diocesan Museum. This afternoon, we’ll gather for a bike fitting and briefing to get you ready for your Tuscan adventure!
Overnight Location: Hotel in Cortona
Distance: N/A
Meals: N/A
Day 2 Loop ride to Trasimeno Lake and surrounding hills
Pedal your way to the picturesque shores of Lake Trasimeno, where Hannibal famously defeated the Romans after crossing the Alps with elephants! If you’ve got extra time, take a boat ride to Isola Maggiore for stunning views. On your way back to Cortona, cycle through the rolling hills that inspired Frances Mayes in Under the Tuscan Sun. For a more relaxed ride, opt for the scenic route to Castiglione del Lago, a charming village perched on a cliff, and enjoy a leisurely afternoon back in Cortona.
Easier option to Castiglione: daily distance 64 km (40 miles); elevation gain + 715 m (2345 ft)
Harder option to Lake Trasimeno: daily distance 53 km (33 miles); elevation gain +1022 m (3352 ft)
Overnight Location: Hotel in Cortona
Distance: Varies depending on the option selected.
Meals: Breakfast
Day 3 Bicycle to Montepulciano and Pienza
Today, ride to Montepulciano, renowned for its famous Vino Nobile di Montepulciano. Wander through the medieval streets and stop by one of the local wine cellars for a tasting. After enjoying lunch, head towards Pienza, one of the first planned Renaissance towns. With the help of architects during the 16th century, Pope Pius II transformed his humble hometown into a breathtaking masterpiece.
Overnight Location: Hotel in Pienza
Distance: 53km, 717m / 2,352ft elevation gain
Meals: Breakfast
Day 4 Loop ride in the Orcia Valley
Today’s loop ride takes you deep into the Orcia Valley, a stunning landscape known for its vibrant hills that change color with the seasons. Cycle through the tiny medieval village of Monticchiello and experience the valley’s unique charm. As you return to Pienza, take time to sample the local wines and cheeses, including the famous Pecorino, aged under chestnut leaves for a rich, smoky flavor. Choose between two ride options:
Short option: 35 km (22 miles), +642 m (2106 ft) elevation
Long option: 52 km (32 miles), +793 m (2601 ft) elevation
Overnight Location: Hotel in Pienza
Distance: Varies depending on the option selected.
Meals: Breakfast
Day 5 Bicycle to the wine town of Montalcino
Start your day with a scenic ride along the ridgeline of the bare clay hills north of Pienza, where cypress trees mark the entrances to isolated Tuscan farms. Stop for a cappuccino in the charming village square of Trequanda before continuing your journey through the Asso River Valley and its surrounding vineyards. Head toward the historic hilltop town of Montalcino, once home to Sienese nobles, and now famous for its world-renowned Brunello di Montalcino wine.
Overnight Location: Hotel in Montalcino
Distance: 54km (34 miles), 979m / 3211ft elevation gain
Meals: Breakfast
Day 6 Loop ride to Bagno Vignoni and the Abbey of Sant Antimo
Today’s scenic route starts with a visit to the Abbey of Sant Antimo, a stunning 8th-century landmark. As you ride on, enjoy panoramic views as you climb to Castiglione d’Orcia and descend into the beautiful Orcia Valley. At the valley’s base, take a second chance to explore Bagno Vignoni, a picturesque village known for its thermal baths. Cycle through San Quirico d’Orcia, a key stop along the Via Francigena, the ancient route linking Rome to northern Italy. End your ride with a climb up to Montalcino.
Options:
Short option: (S. Antimo & back): 22 km (14 miles), +390 m (1279 ft) elevation gain
Long option: (through San Quirico and Bagno Vignoni): 55 km (34 miles), +1215 m (3753 ft) elevation gain
Overnight Location: Hotel in Montalcino
Distance: Varies depending on the option selected.
Meals: Breakfast
Day 7 Bicycle to Siena
Today, you’ll experience the full beauty of Tuscany as you leave Montalcino and pedal towards Siena. The landscape transitions from the lush green fields and forests of the Orcia Valley to the striking barren clay hills of Central Tuscany. Along the way, pass by the historic Monastery of Monte Oliveto Maggiore and ride through the eroded chalk hills of the Crete Senesi. As you enter Siena, you’ll be transported back in time. This medieval city, once a powerful rival to Florence in the 1300s, remains one of Italy’s best-preserved cities.
Overnight Location: Hotel in Siena
Distance: 62 km (39 miles), +956 m (3136 ft) elevation gain
Meals: Breakfast
Day 8 Departure
After breakfast, your Tuscan adventure comes to an end, but Siena is worth an extra day or two to explore. With frequent and fast trains, you can easily travel to Florence or head south to Rome.
Overnight Location: N/A
Distance: N/A
Meals: Breakfast
2026 Pricing for Cortona to Siena Cycling Tour The departures are available starting every Monday from March 1st through October 31st, 2026.
The starting price for two people sharing a double or twin room is EUR1615 per person.
An aluminum bike rental is EUR195, and an e-bike is EUR350.
Accommodation on Cortona to Siena Cycling Tour
This tour is based in Hotels. Hotels on this trip are 3 and 4-star and offer modern conveniences that can make this trip more pleasant. Rooms may include amenities such as a minibar, concierge service, and a city view.
Single Rooms and Solo Travellers
Rooms are based on double occupancy. A single supplement is available for a private room when possible. Solo travelers may need to pay an additional fee.
What’s Included in the Cortona to Siena Cycling Tour?
Meals
7 breakfasts are included.
Accommodations
Accommodations for 7 nights are included. Additional nights before and after the tour are not included but can be added as a supplement.
Transportation during the Tour
Luggage transfers are included throughout the tour.
Also included
- Route Information that can be accessed through digital mobile app
- Excursions mentioned in the itinerary
- Bike fitting and briefing in English by our professional staff at tour start
Not included
- Flights
- Meals, drinks, or snacks not previously mentioned
- Gratuities for tour guides or other staff if desired
- Entrance to museums or other activities not indicated as included
- City hotel tax
- Insurance
- Bicycle rental
Optional Extras
- Additional nights before or after the tour
- Single occupancy upgrades
- Optional activities or excursions
-
- Wine Tasting in Montalcino
- Guided visit of Siena
- Cooking Class
- Bike Rental
-
- Aluminum hybrid: €170
- Premium Titanium road or hybrid: €215
- Touring E-bike (hybrid with straight handlebar): €295
- How hard is the Cortona to Siena Cycling Tour?
- Do I need a visa to travel to Italy?
- Are meals included on the Cortona to Siena Cycling Tour?
- Do I need insurance?
- How do I get to Cortona to start this tour?
- Is the Cortona to Siena Cycling Tour in English?
- Where does the Cortona to Siena Cycling Tour end?
- Do I need special vaccines to travel to Italy?
- Are there any travel restrictions for Italy?
We rate this tour a 3/5 difficulty. With multiple-night stays, you’ll have the flexibility to choose between longer or shorter rides, with each day featuring some hills, allowing you to decide the distance and number of climbs based on your preference.
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.
To get to Cortona from Florence Airport, take a 30-minute trip to the main train station, Firenze S. Maria Novella, by either shuttle bus or taxi. If you choose a taxi, make sure to agree on the fare beforehand, plus any luggage fees. The ride typically takes around 15–20 minutes, depending on traffic. Alternatively, you can take one of the several trains running daily between Florence and Cortona, with the journey usually lasting about 1 hour and 30 minutes.
This is a self-guided tour without guide services, but all tour materials are provided in English.
Your tour concludes in Siena.
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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