Postcard Southern Tuscany - Cycling Cortona to Siena

Overview

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 stunning 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 – with less packing and unpacking, you can take a day off if desired, or choose to 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! 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. 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. 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. 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). 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 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. 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. The beauty of multiple-night stays is you can take long or short rides at your pleasure. Each day involves some hills but in most cases you decide how far and how many. You will ride an average of 46 km with 780 meters of gain, making it perfect for active people and intermediate cyclists. Day 2-4 and 6 you'll have longer options available in case you seek for more challenges. 7 nights in 3- and 4-star lodgings All breakfasts All Classic self-guided tour inclusions Optional activities include Pienza cheese and wine tasting, Pienza cheese making demo, Pienza truffle hunting activity, Wine Tasting in Montalcino, Guided visit of Siena, and Cooking classes available in various tour locations! This tour is available between March 1 and October 31. Starts every Monday. Other start days available by request (extra fee applies). Please note that starting on certain days of the week will make some visits impossible (such as museums or tastings). Join this itinerary back to back with our Classic Tuscany – Florence to Pisa tour (8-day) for a true Grand Tour of Tuscany! Don't want to break a sweat but still explore this amazing (and hilly) region? You can with our top-notch e-bikes! More pedaling in breathtaking landscapes and marvelous historical Italian towns? Take a look at our Umbria 8-day tour. Prices for 2026: Low season €1425, High season €1525. Single supplement €285. Solo traveler departures €785. Prices for 2027: Low season €1470, High season €1570. Single supplement €335. Solo traveler departures €825. Prices per person, based on double occupancy; minimum 2 participants per departure. Lodging upgrades & extra nights are available: please inquire GPS device rental (€50), as well as a printed roadbook (€45, second copy €15) are available at an optional extra fee. Group Discounts are available for participants booking together on the same departure! Please inquire! For more ways to save, see our discounts and promotions page. We offer quality bikes in different styles, all great options for this bike tour. Our bikes are maintained and delivered in optimal working condition. The prices below are per bike for the duration of the tour, including delivery to starting point in Cortona and collection from ending point in Siena. Bike rental rates: Aluminum hybrid: €160, Premium Titanium road or hybrid: €200, Touring E-bike (hybrid with straight handlebar): €280, Tandem: €295 (priced per bike, for 2 cyclists), Tag-along or kid trailer: €80. Bike rental insurance is available for purchase with all our rental bikes – see details in the Bike Rental Insurance section of our Terms and Conditions page. Starting point: Cortona. We recommend flying into Florence Airport or Rome Fiumicino Airport (FCO). Options for getting to the starting hotel: From Florence airport to Cortona: shuttle bus or taxi to Florence main train station, then train to Cortona (approx. 1h30min). From Rome Fiumicino Airport: train, shuttle bus or taxi to Rome Termini, then 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. Ending point: Siena. You can fly out from Florence (FLR) or from Rome’s Fiumicino Airport (FCO). Airport transfers from Siena: Train to Florence SM Novella (1h30min - 2h, some require a connection). Bus Siena-Florence (approx. 1h30min, faster than train but more expensive if purchased on board). Taxi to Siena train station or to Florence (reservation through hotel front desk recommended). 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.)

Daily Ride Schedule

Accommodation & Services

Accommodation

Hotel

What's Included