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Italy Bike Tours >> Tuscany Bike Tours >> Siena to Cortona Tour

Siena to Cortona Tour - Bike Tour Tuscany

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Difficulty: Moderate - Difficult
Duration: 3 Days
Distance: 150 KM
Begin/End: Siena / Cortona

This three day bike tour through Tuscany will test your leg muscles. While most of the ride will be on rolling hills, there are steep climbs into the cities themselves.

Cycling through the hillsides from town to town, expect to see medieval villages with cobblestone paths, walled cities and chapels dotting the countryside.

This area is strikingly beautiful, and the towns themselves are relaxed and used to tourists. While this bike tour of Tuscany is only three days long, you may find yourself wanting to say longer and enjoy the town's charms.

The first day goes through wheat fields until you reach Montalcino. From there, the terrain changes to vineyards –the famous Brunello wine comes from here- and finally an easy descent into Cortona where you end your route.

When To Cycle

April – July and September – October are the best months for a bike tour Tuscany style. July and August are unbearably hot and even the smallest areas are overrun with tourists.

Getting Back To Siena

There are six daily trains from the Buonconvento station (25 minutes; €2.50) Be sure to purchase your supplementary bike ticket beforehand (€3.50); this station does not sell them!

Bike Tour Tuscany Route

Day 1: Siena - Montalcino (5 hrs, 56km)

The terrain varies from bare, rolling hillsides to lush, forested areas and ends up in the Brunello wine capital Montalcino. The ride is mostly hilly until you reach Asciano; then the ride turns noticeably steeper for the last 6km.

Leaving Siena, you'll head right through several roundabouts and follow the signs to Arezzo. Keep an eye out for the Taverna D'Arbia Nord exit (7.3 km) to escape the traffic. From here you'll enjoy a number of wheat fields and olive gardens (not the restaurant). Depending on your luck, there may be a number of fresh cheese stands offering pecorino and ricotta cheeses.

There's a strong but short-lived descent into Buoconvento. From there it's a grueling – but beautiful – ascent into the wonderful wine region and Tuscan gem, Montalcino.

Day 2: Montalcino - Montepulciano (5 hours, 58km)

This route is full of hair-raising descents and arduous climbs through jaw-droppingly beautiful landscapes. Highlights include the Sant'Antimo church (home of Gregorian chanting) the Roman baths of Bagno Vignoni and the postcard-perfect village of Pienza (a true highlight of any cycling tour in Tuscany).
From Montalcino, you'll lose all elevation gained yesterday. The road is paved, but rocky in certain parts. You'll cycle past the Romanesque Abbazia di Sant'Antimo, and monastery built by Charlemagne in 781 AD.

The road to the Abbey is a steep, winding path through wheat fields, vineyards and olive groves. Stop in for some Gregorian chants (there aren't usually many monks there, but it does add to the sense of peace and solitude). The bell tower leans slightly over and remains in constant view.

From the Abbey it's a long, hard climb up to Castiglione d'Orcia, though the swift descent into Bagno Vignoni is well worth it. These thermal baths – used by Romans - are beautiful around dusk.

From the Roman baths it's a 10 km cycle to Pienza. Here you have two choices: either stay the night in Pienza (which is gorgeous) or pedal the extra 15 km to Montepulciano. This last part is relatively flat, except for the last half km or so, which is painfully steep.

Day 3: Montepulciano- Cortona (3 hours, 35 km)

While this ride is much easier than previous days, the scenery is not as good. Don't get us wrong – you'd be hard pressed to find an unpleasant area to cycle in Tuscany – but after a few days of olive trees and vineyards, you may yearn for change.

The ride is a series of rolling ups and downs until a steep ascent into Cortona. Sunflowers line the way the closer you get to this larger hill town, which overlooks the valley from a stern looking ridge. Cortona is nice, but crowded. We suggest catching the train back to Siena, Montalcino or Pienza for the night.

Bike tours tuscany style, are fun and challenging. It might be tough on the climb up, but you'll be glad you did it with endless memories to take with you on your journey.

Siena to Cortona Tour Map


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Tuscany Bicycle Tours

TOUR NAME DURATION DISTANCE DIFFICULTY
Florence to Siena Tour 2 Days 101.7 KM Moderate - Difficult
Siena to Buonconvento Tour 4-7 Hours 75.8 KM Moderate - Difficult
Siena to Cortona Tour 3 Days 150 KM Moderate - Difficult
Siena to Massa Marittima Tour 3 Days 202.5 KM Moderate
Arezzo to Florence Tour 1-2 Days 115.6 KM Moderate - Difficult
Portoferraio Tour 5-9 Hours 92 KM Moderate - Difficult
Castelnuovo di Garfagnana to Viareggio Tour 3 Days 155.3 KM Moderate - Difficult
Orbetello to Montalcino Tour 3 Days 179.8 KM Moderate

 

 

 

 

 

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