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Bicycle Tours — Italy

Postcard Southern Tuscany - Cycling Cortona to Siena

Classic Self-Guided – Cortona to Siena – 8 days

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!

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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.

    Accommodation: Hotel San Luca, or similar.

  • 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 distance:53 km (33 miles)
    Elevation gain: +1022 m (3352 ft)

    Accommodation: Hotel San Luca, or similar.

  • 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 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 (33 miles), with +717 m (2352) elevation gain. Long option: 66 km (41 miles), with +757 m (2483 ft) elevation gain.

    Accommodation: Relais Il Chiostro di Pienza, or similar.

  • 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).

    You have two options for your ride today:

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

    Accommodation: Relais Il Chiostro di Pienza, or similar.

  • Day 5

    Bicycle to the wine town of Montalcino

    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: +909 m (2982 ft)

    Accommodation: Hotel Dei Capitani, or similar.

  • Day 6

    Loop ride to Bagno Vignoni and the Abbey of Sant Antimo

    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 (14 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.

    Accommodation: Hotel Dei Capitani, or similar.

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

    Accommodation: Hotel Il Chiostro del Carmine, or similar.

  • 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
Access to smartphone app with tracks and digital roadbook
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
Any type of insurance (medical, trip cancellation and interruption, baggage, bike rental)

Solo Traveler and Private Group departures available please inquire.

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

Private transfers (please inquire for price and availability)
Florence airport - Cortona
Siena - Florence airport

Extra nights: If you'd like to add nights before or after the tour, please inquire - we will be happy to provide a quote and add the nights to your tour package.

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.
  • ________________________________________

    Navigation and roadbook:
    On our self-guided tours, detailed tour information and route navigation tracks are provided through the free smartphone app Ride With GPS - our "digital roadbook" - which includes daily routes, maps, elevation profiles, and ride descriptions; schedules and hotel itinerary; cultural and sightseeing information, visit suggestions; emergency numbers and more, all stored in one organized, easy to use app. Downloading the app content also allows for offline mode navigation. Participants can also upload the routes to their own GPS device, and even print the detailed route notes before leaving home

    On our self-guided tours, GPS device rental, as well as a printed roadbook, are available at an optional extra fee:
  • GPS device rental: €50
  • Printed roadbook: €45 (second copy of printed roadbook €15)

  • For more information on our navigation options, as well as the smartphone app, please read our blog: What's it like to navigate on our self-guided tours?.

    Luggage transfers
    Luggage transfers are included in your package. The luggage is normally collected from 09.30 at the reception of the hotel and is delivered at the following hotel by 15.00 hrs. Please use the luggage tags provided by Cycle Europe on all your luggage being transferred. Please have your luggage ready before the driver comes to collect it, otherwise 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.

    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.

    Tour code: itbs3434
    Countries Italy
    Begin/End Cortona / Siena
    Arrive/Depart How to get there and away
    Florence Airport (FLR) / Rome Fiumicino (FCO)

    Starting point: Hotel S. Luca - Piazza Garibaldi, 1, Cortona
    - The airports closest to the tour start are Florence Airport and Rome Fiumicino Airport (FCO).

  • 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.

  • The 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: 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 frontdesk 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.)
    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)

    Difficulty description: The beauty of multiple-night stays is you can take long or short rides at your pleasure. Each day involves some hills but you decide how far and how many.
    Rating 301
    Terms Terms & Conditions
    Dates Prices Single Supplement
    Dates This tour is available from March 1 to October 31

    * 2024 price, per person, based on double occupancy; minimum 2 participants per departure.

    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 (such as museums or tastings) impossible.

    Solo traveler departures are also available (only one person on the departure), with a supplemental fee of €650. This fee includes the cost of the single/double room supplement, as well as a GPS unit with the pre-loaded routes.

    Group Discounts are available for 4 or more participants booking together on the same departure! Please inquire for details through our contact form below.

    For more ways to save, see our Discounts and Promotions page (hint - consider coming in the low-season!)


    High-Season surcharge (May, June, September and early October): a €100 per person surcharge is applied on high-season departures. If joining an existing, confirmed departure date, the fee may be waived - please inquire

    2024 confirmed departure dates:

    May 6, 13
    June 3
    September 30

    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: €130
    Premium Titanium road or hybrid: €170
    E-bike (hybrid with straight handlebar): €255
    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.


    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 !

    If you love pedaling surrounded by breathtaking landscapes, take a look at our Umbria Tour. You can choose between the 10-day version or the 8-day version.

    Additional useful information:

    • Do you have any questions about how our bike tours work? Check out our FAQs page!

    • Curious about the difference between our Casual and Classic self-guided tours? Check out our introduction blog on Casual Self-Guided Tours.

    • We offer various tools for navigation - this page details what it's like to navigate on our self-guided tours.

    • If the self-guided formula isn't right for you, check out this blog introducing the differences between Guided and Self-Guided Tours.
    Prices €1295 per person*

    Single Supplement €245 (in double room for single use)
    Next Step Request space on this Bicycle Tour »
    • It was our first self-guided tour and it is a great way to go! The navigation tools worked perfectly and led us to mostly back country roads that didn't have much traffic and were beautiful!! They also led us to sweet hilltop towns that were fun to explore. The hotels were certainly adequate and the breakfasts gave us a good start to our day. Our bags were always waiting for us at our daily destinations. The bikes were perfect for the terrain we were riding ~ light, with lots of gears! The lunch towns and the destination towns provided lots of options for delicious Italian meals!! Having a second day in some of the towns gave us the opportunity to visit some of the cultural places and interact with the locals. It was a wonderful, fun, well-supported, well-organized experience!! My favorite?! The landscapes were amazing! Day after day, mile after mile of gorgeous scenes from the saddle of a bike. A perfect way, the very best way, to explore a country.

      Rita B.

    • 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.
      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.
      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.
      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