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Self-Guided Bicycle Tours — Italy

Bicycling Cortona, Montalcino and Siena in Southern Tuscany

This self-guided tour covers a stunning part of Tuscany starting from Cortona made famous by Frances Mayes in her book "Under the Tuscan Sun" . From Cortona you pedal to the beautiful Val d'Orcia recognized by UNESCO as a "World Heritage Landscape" for its unique blend of human and natural environments. This is a relaxed tour with three two-night stays so you are not always packing and you can take a day off if you wish. 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; you'll taste homemade pasta, local cheese and typical soups of Tuscany, so Buon Appetito!

For more information download the Tour Factsheet

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  • Day 1

    Arrive today in Cortona

    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.

  • Day 2

    Loop ride to Trasimeno Lake and surrounding hills

    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 Mileage: 54 km (34 miles)

  • Day 3

    Bicycle to Montepulciano and Pienza

    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 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 Mileage: 52-66 km (32-41 miles)

  • Day 4

    Loop ride in the Orcia Valley

    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). Daily Mileage: 34-52 km (21-33 miles)

  • Day 5

    Bicycle to the wine town of Montalcino

    Highlights: Brunello di Montalcino

    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 is 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 town sheltered summering Sienese nobles during the 16th century, but today is more famous for producing one of Italy's premier red wines, Brunello di Montalcino. Daily Mileage: 54 km (33 miles)

  • Day 6

    Loop ride to Bagno Vignoni and the Abbey of Sant Antimo

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

    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. Continue on to the tiny Medieval spa of Bagno Vignoni, famous for its thermal baths since Roman and Etruscan times. Our scenic route takes you then to the famous Abbey of Sant'Antimo before heading back to Montalcino. Daily Mileage: 22-54 km (14-34 miles)

  • Day 7

    Bicycle to Siena

    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 Mileage: 61 km (38 miles)

  • Day 8

    Tour ends in Siena

    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.

Includes 7 nights in 3 or 4 star hotels; 7 breakfasts; use of a high quality titanium racing or hybrid bicycle; bike delivery and collection; use of GPS with preloaded tracks; roadbook and map; suggestions for dinners; luggage transfers
Countries Italy
Begin/End Cortona / Siena
Arrive/Depart Florence Airport (FLR) or Rome Fiumicino (FCO)
Total Distance 165 - 346 km (103 - 216 miles); 2 night stays allow for rest days for those who wish
Daily Distance 0 - 67 km (0 - 42 miles)
Rating 301
Notes You can make this a 5 to 12 days tour. Ask for details. Tour Factsheet
Terms Terms & Conditions
Dates Prices Single Supplement
Dates Tour departs every day.
Hotel upgrade possible (ask for details).
City taxes not included.

GROUP DISCOUNTS 5% (on groups of 4 or more)
Electric bikes available for an extra charge
Prices €1390 Single Supplement € 390 (singles travelling with others pay € 290)
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  • We asked to stay in Sarteano & we're thrilled to have done so. The hotel was delightful & charming, the restaurant was every bit as good as the Michelin guide suggested and the multi-generational family that ran it were the ultimate hosts. While the town itself is modest, we very strongly recommend this location for an overnight stay. One of the highlights of the trip -- and a very pleasant day ride from Cortona! Tick sheets were fine & pre-loaded GPS routes or each day were wonderful! Trip book with notes, suggestions & recommendations were very helpful & well done . A wonderful trip, excellent pre-trip planning support, very useful & personalized trip kick-off briefing /bike fitting, & most of all absolutely impeccable execution on all logistics & support during the trip. We will definitely look to BikeRentalsPlus for future self guided trips.

    Jim N.
    Sisters, OR
    April 2016

  • Notes were great and maps were accurate. We used them every day and reviewed them the night before to plan our next day's ride. Hotels were all great. So nice to have a local pick the accommodations-you know the best places to go. Sarteano stood above the rest. A magical setting, wonderful ancient building, food from heaven, great hosts. Wow.

    Katerine A.
    Bend, OR
    April 2016

  • Thanks for avoiding as much traffic as possible. The route into Sienna was truly ingenious. We needed both the directions plus the garmin and faith in your outfit...but it certainly avoided lots of traffic. The rides were beautiful...both loops took us through interesting and at times stunning landscapes.

    Robert P.
    Northampton, MA
    Sept 2016

  • Route notes provided were very clear and the language precise which is important to ensure cyclists dont get needlessly lost. I appreciated notes on approaching places to get refreshments (water, coffee, food). The hotels were all four very good and the breakfast provided was consistently good with good service and high quality items. The country side was beautiful, the destination towns were all attractive and interesting and charming. It was a very enjoyable tour. Very challenging but worthwhile and we received support from the staff anytime we asked for it. It was well planned and I highly recommend it.

    Miguel G.
    Puerto Rico
    June 2016