Self-guided: Southern Tuscany – Cycling Cortona to Siena

  • Length 8 days
  • From EUR1295
  • Style/Level Self-Guided 1.0
  • Countries Italy
  • Begin/End Cortona / Siena

Starting in Cortona – made famous by Frances Mayes in her book “Under the Tuscan Sun” – this self-guided tour covers a stunning part of Tuscany . You will cycle through the beautiful Val d’Orcia, (recognized by UNESCO as a “World Heritage Landscape” for its unique blend of human and natural environments. With three 2-night stays, this is a relaxed cycling holiday – you are not always every day, can take a day off if desired, and can also explore each magnificent tour destination deeper. The tour ends in Siena where you may wish to spend an extra day or two. Of course, food and wine play an important role on this tour – homemade pasta, local cheese, the typical soups of Tuscany, as well as the renowned Brunello wine. Buon Appetito!


  • The towns of Cortona, Montepulciano, Pienza and Montalcino

  • Rolling hills of Tuscany

  • Siena and its remarkable historical center

  • The dreamy landscapes of the Val d’Orcia

    Extra meals & activities: (please inquire for price and availability)

  • Wine Tasting in Montalcino
  • Guided visit of Siena
  • Cooking classes available in various tour locations! Organized by Le Cesarine, experts in Italian culinary experiences. You will be hosted by a local at their home – your “Cesarina” – in a class that lasts about three hours, during which you will help the Cesarina prepare three courses. In the fourth and final hour, you will enjoy the meal (lunch or dinner) which you prepared during the class. Water and one bottle of house wine for every 3 people are included.


Keep in mind

We work hard to maintain consistency across all of our tours, but some trips have unique differences. Here are some things to keep in mind about this tour.

Solo Traveler and Private Group departures available please inquire.

  • START DAYS: This tour departs any Monday between March 1 and October 31. Other start days of the weeks may available by request, for an extra fee. Please note that changing the start day could make some cultural visits and activities impossible.
  • HOLD A SPACE: Request a departure date by clicking the blue “Hold a space” form.
  • DATES LISTED BELOW: These are booked departures. Multiple parties can join any trip.
  • PRICING: Based on double occupancy. Solo departures may require supplemental fees.
  • HIGH SEASON SURCHARGE: $400 per person for bookings in May, June, September and early October.

Date Price Private room fee Note

Download Itinerary

We’ll send you a link to a full day by day tour itinerary that can be downloaded and printed so you can review all the details online and offline. This packet also includes details about what to expect on tour and arrival and departure details.
Tour date(Required)
Have you traveled with us before?(Required)
Opt-in to weekly news, recipes, and tour updates

  • Total distance 165 – 346 km (103 – 216 miles); 2 night stays allow for rest days for those who wish
  • Average daily distance 0 – 67 km (0 – 42 miles)
  • Tour style Self-Guided
  • Tour level 1.0

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.

Accomodation: Hotel S. Luca, or similar.

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”.

Daily distance: 54 km (34 miles)
Elevation gain: + 1022m (3353ft)

Accomodation: Hotel S. Luca, or similar.

Meals : Breakfast

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. You have two options for your ride today: Short option: 53 km (32miles), with + 717m (2112ft) elevation gain. Long option: 66 km (41 miles), with + 757m (2483ft) elevation gain. Accomodation: Relais Il Chiostro di Pienza, or similar.

Meals : Breakfast

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: 35 km (22 miles), with + 613 m (2011 ft) elevation gain.
Long option: 52 km (32 miles), with + 777 m (2549 ft) elevation gain.

Accomodation: Relais Il Chiostro di Pienza, or similar.

Meals : Breakfast

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: 54km (33.5 miles)
Elevation gain: + 909 m (2982 ft)

Accomodation: Hotel Dei Capitani, or similar.

Meals : Breakfast

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): 22 km (13,7 miles), with + 370 m (1214 ft) elevation gain.
Long option (through San Quirico and Bagno Vignoni): 55 km (34 miles), with + 1144 m (3753 ft) elevation gain.

Accomodation: Hotel dei Capitani, or similar.

Meals : Breakfast

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: 63 km (39 miles)
Elevation gain: + 1000 m (3280 ft)

Accommodation: Hotel Il Chiostro del Carmine, or similar.

Meals : Breakfast

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. City hotel taxes are not included.

Meals : Breakfast

Visit our Tour Level page to learn more about terrain levels and how we determine day and tour levels.

Pre-trip planning checklist

Already taken this tour? Be the first to add a review!