Postcard Southern Tuscany - Cycling Cortona to Siena

Highlights: Ancient Etruscan city of Cortona, Etruscan Museum

Arrive in the spectacular hill town of Cortona today looking over the Chiana River valley (the "Val di Chiana") famous for the chianina steak. Cortona offers the perfect introduction to Tuscany since its founding as an Etruscan town dates to 600 BC. Today Cortona retains the look and character of a Medieval city. Take time today or tomorrow to see the Etruscan Museum or the Diocesan Museum with its Fra Angelico paintings. We'll meet this afternoon for bike fitting and briefing.

Accommodation: Hotel San Luca, or similar. Upgrades available - please inquire for details

Highlights: Trasimeno Lake

Ride to the shores of Lake Trasimeno today. The lake is famous for Hannibal's defeat of the Roman army after crossing the Alps with elephants! If you have the time you might want to take a boat ride on Lake Trasimeno to Isola Maggiore. Continue back to Cortona through the hills made famous by Frances Mayes in her book "Under the Tuscan Sun." You may also choose an easier ride on the lower hills to Castiglione del Lago, a village perched on a cliff overlooking the lake, and have more time to enjoy Cortona this afternoon.

Short option to Castiglione: daily distance 64 km (40 miles) - Elevation gain + 715 m (2345 ft) - Terrain type hilly 
Long option to Lake Trasimeno: daily distance 53 km (33 miles) - Elevation gain +1022 m (3352 ft) - Terrain type hilly

Accommodation: Hotel San Luca, or similar.

Highlights: Vino Nobile di Montepulciano, Renaissance towns of Pienza

Montepulciano is famous for the production of Vino Nobile di Montepulciano, and your ride today takes you there. After a stroll along the medieval streets of this village, you can stop to visit one of the typical wine cellars in town. Take time for lunch before heading to one of the first planned Renaissance towns, Pienza. With the help of a number of prominent architects Pope Pius II turned his small hometown into a piece of art in the 16th century.

Daily distance: 53 km (33 miles) 
Elevation gain: 719 m (2352)
Terrain type: hilly 

Accommodation: Relais Il Chiostro di Pienza, or similar. Upgrades available - please inquire for details

Highlights: UNESCO World Heritage Landscape of Val d'Orcia

Your loop ride today takes you through heart of the Orcia Valley. This valley is unique in Tuscany. Composed of poor clay soils the rounded hills change color with the seasons from bright greens and reds in spring to soft gold in summer and deep gray when the fields are ploughed in late fall. The margins of the valley are lined with volcanic plateaus allowing for better soils to cultivate grapes and olives. Cycle through the tiny Medieval village of Monticchiello before heading back to Pienza. Take a walk and sample the local wines and cheeses (we highly recommend the Pecorino that is wrapped in chestnut leaves and aged under a bed of ashes allowing for uniform drying and aging).

You have two options for your ride today:

Short option: daily distance 35 km (22 miles) - Elevation gain +642 m (2106) -  Terrain type rolling hills
Long option: daily distance 52 km (32 miles) - Elevation gain +793 m (2601 ft) - Terrain type hilly

Accommodation: Relais Il Chiostro di Pienza, or similar. Upgrades available - please inquire for details

Highlights: Montalcino, in the heart of the Orcia Valley

This morning starts with a ride on the ridgeline of the bare clay hills north of Pienza. Cypress trees mark the entrances to isolated Tuscan farms on distant hills. The quaint village square in Trequanda provides an excellent mid-morning cappuccino stop. As you continue down the Asso River Valley, you leave the clay hills and ride through vineyards as you make your way to the Etruscan village and wine town of Montalcino. This fortified hilltop town sheltered summering Sienese nobles during the 16th century, and today is more famous for producing one of Italy's premier red wines, Brunello di Montalcino

Daily distance: 54 km (34 miles) 
Elevation gain: 979 m (3211 ft) 
Terrain type: hilly 

Accommodation: Hotel Dei Capitani, or similar. Upgrades available - please inquire for details

Highlights: Abbey of Sant Antimo, Bagno Vignoni, San Quirico d'Orcia

Our scenic route takes you first to the famous Abbey of Sant Antimo dating back to 8th Century. Continue on for majestic views as you climb to Castiglione d'Orcia. Glide down into Orcia Valley and at the bottom you have a second opportunity to visit Bagno Vignoni. Cycle through San Quirico d'Orcia, which during the early Middle Ages gained great importance thanks to the Via Francigena. This important artery connected Rome to the northern part of Italy. Montalcino is then just a climb away.

You have two options for your ride today:

Short option: (S. Antimo & back): Daily Distance: 22 km (14 miles) - Elevation gain +390 m (1279 ft) - Terrain type rolling hills
Long option: (through San Quirico and Bagno Vignoni): Daily Distance: 55 km (34 miles) - Elevation gain +1215 m (3753 ft) - Terrain type hilly

Accommodation: Hotel Dei Capitani, or similar.

Highlights: Abbey of Monte Oliveto Maggiore, the "Crete Senesi", Siena

The full beauty of the Tuscan landscape with the lush green fields and forests of the Orcia Valley and the barren clay hills of Central Tuscany unfold before you today as you leave Montalcino and pedal to Siena. You'll pass by the historic monastery of Monte Oliveto Maggiore and spin along the eroded chalk hills of the Crete Senesi. Siena remains Italy's best-preserved medieval city and rivaled Florence for dominance over Tuscany during the 1300s. You'll be transported back in time as soon as you enter the city walls.

Daily distance: 62 km (39 miles) 
Elevation gain: +956 m (3136 ft) 
Terrain type: hilly .

Accommodation: Hotel Il Chiostro del Carmine, or similar. Upgrades available - please inquire for details

Highlights: Enjoy Siena for another day or two

Your tour ends after breakfast this morning, but Siena is certainly worth another day or two. Trains are frequent and fast to Florence or South to Rome.

PLEASE NOTE : The final itinerary, including hotels and/or activities described here, are subject to changes according to availability. 

Starting point: Hotel S. Luca - Piazza Garibaldi, 1, Cortona

We recommend flying into Florence Airport or Rome Fiumicino Airport (FCO).

Options for getting to the starting hotel:

From the Florence airport to Cortona:
- It’s a 30-minute trip from the airport to Florence main train station (Firenze S. Maria Novella). You can catch a shuttle bus, or a taxi
- If you want to go by taxi, agree on a fare before accepting the ride (plus the cost of the luggage). It takes about 15/20 minutes, depending on the traffic
- There are several trains every day connecting the two cities. The trip is usually 1h30min long

From Rome Fiumicino Airport you can reach Rome Termini train station by train, shuttle bus or taxi and than you can take a train to Cortona.

Meeting time for our self-guided tours is typically set between 2pm and 4pm. We recommend travelers plan accordingly allowing plenty of time to arrive at the determined meeting place. Please note a late fee may be applied for late arrivals - please see our terms page for details.

Final Arrival and Departure Instructions: Detailed pre-travel documents, including your actual hotel details (which may vary from those listed), as well as exact meeting time, will be sent via email before your departure.
 

Ending point: Hotel Santa Caterina - Via E.S. Piccolomini, 7, Siena

You can fly out from Florence (FLR) or from Rome’s Fiumicino Airport (FCO).

Airport transfers:
- Train from Siena to Florence SM Novella takes between 1h30min and 2h (some require a connection in Empoli)
- By bus the trip Siena-Florence is about 1h30min long and it is faster than the train (tickets are more expensive if purchased on board)
- If you want to take a taxi to Siena train station or to Florence, make a reservation through the hotel’s front desk one day in advance. Note that if you take a taxi directly it may cost you more.
- From Florence’s Santa Maria Novella train station to Florence airport, look at the starting section above
- The trip from Siena train station to Rome Termini train station takes from 3h30min to 5h. From Rome Termini train station you can reach Rome Fiumicino Airport by train, shuttle bus or taxi

Private airport transfers available if you prefer to be driven from airport to hotel in a private vehicle transfer, please inquire for cost - we will be happy to include this service in your tour package

Final arrival and departure instructions along with other detailed pre-travel documents, will be e-mailed prior to your travel, with information specific to your departure (including the actual hotels used on your tour dates, which may vary from the hotels listed above.)