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Cycle Europe - serving bicycle travellers since 1972

Bicycle Tours — Italy

Postcard Southern Tuscany - Cycling Cortona, Montalcino, Siena

Classic Self-Guided

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 Brnunello. Buon Appetito!
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2021 Early Bird Booking Discount available!
Book by May 15th, 2021 to receive €100 off per person.

Free premium bike rental!
Available on all departures through July 31st, 2021, the rental fee for our premium titanium-frame road or hybrid bikes is waived (when full tour package is paid as per our regular t&c's).

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For more detailed tour information download the Tour Factsheet

Request space on this Bicycle Tour »

  • 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.


    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.

Includes Includes: 7 nights in 3- and 4-star lodgings; all breakfasts; bike fitting and briefing in English by our professional staff at tour start; GPS device with pre-loaded navigation routes (one for every two cyclists); access to smartphone app with tracks and digital "roadbook"; printed roadbook with detailed daily information, maps and more; luggage transfers

Not Included: Travel to and from the tour start and end; bicycle rental (see Prices tab); entrance to museums or other activities; city hotel tax (2 to 5 euro per night per person, to be paid locally by traveler); Any meals or beverages not indicated as included.

Solo Traveler and Private Group departures available - please inquire.

Lodging Upgrade: Room upgrades are possible in some hotels - please inquire for prices and availability

Extra nights available upon request - please inquire about adding nights along the itinerary or before/after the tour.

- In Florence, extra hotel night: approx. 65 euro per person, depending on season and availability.
- In Lucca or Pisa, also available – 2021 rates coming soon.

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.
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 Navigation and roadbook:
On our CLASSIC self-guided tours, detailed daily information and route navigation are provided through a GPS device (one included for every two cyclists), a smartphone application, as well as a printed roadbook with thorough daily descriptions and maps. Our app allows you to download the information into your smartphone, where you can the daily routes even in offline mode. Hotel itinerary, daily ride descriptions, cultural information, visit suggestions, elevation profiles, and emergency numbers are all stored in one organized place. Downloading maps and routes also allows you to navigate in offline mode. If you prefer, you can download the routes into your GPS device and print the detailed route notes before leaving home and use them on tour, or rely on the detailed roadbook that we will print for you and delivery before the tour start

For more information on the smartphone app, visit RideWithGPS Experiences.

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Luggage transfers are included in your package.
The luggage is normally collected from 09.00 at the reception of the hotel and is delivered at the following hotel by 15.30. Every piece of luggage must be marked with a visible luggage tag. Please make sure yours have correct tags. If your luggage is not ready by the time the driver comes to collect it, you may have to pay a local taxi for the service.

Please consider that the luggage is not insured during the transport. You need to have your own insurance. Do not leave valuables or fragile items in your luggage.
Normally, the luggage transport service cannot be used by participants to skip the cycling stage. In case you need help to skip the cycling stage, please contact our emergency number and we will arrange it for you.
Terms Terms & Conditions
Dates Prices Single Supplement
Dates Available March 1 to October 31, 2021

Starts every Tuesday*

* Tour can also start other days of the week – supplemental fee may apply (please inquire).

Per person price based on double occupancy with 2 participants per departure minimum; Single rooms and Solo Traveler departures available - see supplemental fees on the right.


2021 Early Bird Booking Discount available! Book by May 15th, 2021 to receive €100 off per person.

Free premium bike rental! Available on all departures through July 31st, 2021, the rental fee for our premium titanium-frame road or hybrid bikes is waived.

Group Discounts for 6 or more participants booking together on the same departure! Please inquire for details through our contact form below.

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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 sweat but still explore this amazing (and hilly) region? You can with our top-notch ebikes !

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Bike Rental options:
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: €120
Premium Titanium road or hybrid: €160
E-bike (hybrid with straight handlebar): €240
Tandem: €280 (priced per bike, for 2 cyclists)
Tag-along or kid trailer: €80

High-Season notes (May, September and early October):
Hotels: may be subject to availability, and a hotel supplemental fee may be applied.
Bike Availability: our premium (titanium-frame) bikes are also subject to availability.

Prices €1170 per person

2021 Early Bird Booking Discount available now!
Single Supplement €290 fee for private, double room

€705 solo traveler fee (only one person on departure)
Next Step Request space on this Bicycle Tour »
  • Although the route was very hilly, we loved everything about our self-guided tour. The itinerary kept us on less-traveled roads as much as possible, and took us through small scenic towns with gorgeous views. We also appreciated the opportunity to tour several monasteries and scenic spots along the way. Our accommodations were very good and we had a hearty, tasty breakfast every morning. The combination of paper maps with precise directions and GPS ensured that we were hardly ever lost. We were also impressed with the quality of the bikes and the expert fitting and orientation we received before we set out. I'd highly recommend this tour for bikers who don't mind lots of elevation change!

    Kathy S.
    USA
    August, 2019

  • The paper maps and instructions were great and the odometer was spot on for every turn which I really appreciated. Great hotels, great routes and maps.

    Traveler .

    April, 2019

  • I was really happy to have an ebike I have ridden with other companies and found Cycle Europe to have better maps and directions. Excellent information and hotels. Loved the site in Montalcino the most - the views were spectacular and the various downhills, unbelievable views. Overall an excellent tour, we had lots of fun and were able to see many thing.

    Nancy C.
    USA
    April, 2019

  • I was very impressed with the informations sheets, lunch and dinner suggestions , the GPS and the written instructions. The whole trip was great. I will be back with my friends and family

    Peggy A.

    April, 2019

  • We had a great time and working with your company in 2014 had us come back again. We''ll see you next spring!

    John C.
    USA
    Sept 2018

  • All in all, the trip exceeded expectations and we appreciate you taking care of us.

    Steve K.
    N. Carolina, USA
    Sept 2017

  • Route notes and gps were great. Easy to navigate and use. Enjoyed the smaller roads and stopping along the routes for coffees/lunch etc.

    Dan E.
    Colorado, USA
    September 2017

  • 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

  • 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