Under the Tuscan Sun Bike Tour | 7 Days
🇬🇧 English-speaking staff
Intermediate+
approx. 280 km
Climb approx. 5,100 m
approx. ¥315,040~
7 days
From Cortona, the town of Under the Tuscan Sun, past the lake, the Val d'Orcia and Brunello country to Siena
A self-guided tour to enjoy freely, without a guide 📅 Choose your own departure date.
A 7-day, 6-night bike tour from Cortona, the hill town made famous by Under the Tuscan Sun, to medieval Siena.
Two nights in Cortona and a ride over the hills above Lake Trasimeno into Umbria. Then through the vineyards to Montepulciano and Pienza, with a loop of the Val d'Orcia and Radicofani.
On to Montalcino via the spa village of Bagno Vignoni and the abbey of Sant'Antimo, and finally to Siena through Monte Oliveto Maggiore and the Crete Senesi.
From Cortona to Siena | 7-Day Itinerary
From hilltop Cortona via Lake Trasimeno, Montepulciano, Pienza, the Val d'Orcia and Montalcino to Siena: a 7-day, 6-night cycling itinerary.
Day 1 | Cortona
The town of Under the Tuscan Sun
Meet at Villa Marsili (Cortona/Camucia station is on the train line). After the bike fitting and briefing, the day is yours.
Stroll the steep medieval streets of the town made famous by Frances Mayes, then enjoy dinner at one of our recommended restaurants.
Day 2 | Lake Trasimeno
From a castle valley to the lake
Ride to Val di Pierle and its castle, built before the 10th century, then climb to the top of Cima di Tuoro for a stunning view of the lake and its islands.
A long descent to Tuoro on Lake Trasimeno, already in Umbria. After a break by the lake, return to Cortona on gentle terrain, with one last climb.
Distance: 50 km | Elevation: +1,042 m / -1,038 m
Day 3 | Montepulciano and Pienza
Through the vineyards to the Val d'Orcia
From Cortona through vineyards to Montepulciano, the "pearl of the 16th century", its beauty intact.
A scenic back road to Monticchiello, gateway to the UNESCO-listed Val d'Orcia, then up and down through a painted landscape to Pienza, the ideal Renaissance town, also famous for pecorino. Two nights here.
Distance: 63.5 km | Elevation: +1,049 m / -1,021 m
Day 4 | Val d'Orcia and Radicofani
A loop along cypress roads
The first 15 km are downhill and gently rolling, then a gradual climb to Radicofani and its 13th-century fortress.
Back along winding cypress-lined roads, with a light lunch in the medieval village of Contignano, and another scenic road to Pienza.
Distance: 63.8 km | Elevation: +1,022 m / -1,029 m
Day 5 | Montalcino
Spa village and Brunello town
First a stop in the spa village of Bagno Vignoni, then on to the abbey of Sant'Antimo, where you may hear the monks' vespers.
In Montalcino, the fortress offers a view over the whole valley you have just ridden.
Distance: 44.4 km | Elevation: +920 m / -876 m
Day 6 | Siena
Abbeys and the Crete Senesi
Along a wooded ridge to the abbey of Monte Oliveto Maggiore, famous for its frescoes, then through the Crete Senesi, Tuscany's "badlands".
Arrive in Siena, often called Italy's best-preserved medieval city, with time to see Piazza del Campo, the Torre del Mangia and the Duomo.
Distance: 56.7 km | Elevation: +1,035 m / -1,217 m
Day 7 | End of tour
A last morning in Siena
The tour ends after breakfast.
Hotels in Cortona, Pienza, Montalcino and Siena
On this tour you spend two nights each in Cortona and Pienza and one night each in Montalcino and Siena.
Cortona | Villa Marsili (2 nights)
A 4-star hotel just inside Cortona's ancient walls. Once the bikes are put away, explore the historic streets, shops, cafés and restaurants on foot. Historic character and warm hospitality.
Pienza | Il Chiostro (2 nights)
A converted 15th-century monastery on Pienza's main street, with a beautiful cloister and a garden pool overlooking the Val d'Orcia.
Montalcino | Vecchia Oliviera (1 night)
Just inside the historic centre next to an old town gate, with breakfast on a panoramic terrace and a small outdoor pool.
Siena | Villa STR (1 night)
A converted 19th-century villa about 10 minutes' walk from Piazza del Campo. Store your bike in the garage and explore Siena on foot.
Tour price and what's included
Tour price (tax included)
€1,790 per person (sharing a double room)
Single room supplement: €690
*The yen price at the top of the page is an estimate and varies with the exchange rate. Payment is made in euros.
Included
6 nights in hotels (4-star and 3-star superior)
6 breakfasts
All luggage transfers, including between hotels
RideWithGPS app (route data and offline navigation)
Trip notes with sightseeing and food tips
Bike delivery and bike fitting at your hotel in Cortona
Bike and equipment collection in Siena
Cicloposse water bottle
Taxes
Not included
Bike rental (extra cost)
City tourist tax (€0.70 to €3 per night, depending on the town)
Bike rental prices
Hybrid bike: €190
Road bike, gravel bike or e-bike: €260
E-gravel bike: €350
*Prices cover the whole tour.
Today's price in yen
Support from Japan
Our local staff speak Italian and English. Our Japan office helps you on LINE with questions, bookings and travel documents, in your time zone (not on site).
Even on your first cycling trip abroad, you can join with peace of mind.
What our Japan office offers
• LINE support, reply usually within 24 hours
• In emergencies, our local staff help in English
• Allergies and diets sent to restaurants in advance
• Travel documents also available in Japanese
Ride and taste Italy to the full, with support from Japan.
First cycling tour? Start here
Fitness, bike choice, what to pack: everything first-timers ask about, in one place.
Have you checked the packing list?
Have you chosen your rental bike?
Questions about the tour? Just ask us!
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