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Bicycle Tours — Italy

Tuscany Gravel - The White Roads of L'Eroica

Self-Guided - Val d’Orcia to Gaiole in Chianti - 7 days

Strade Bianche means 'white roads' in Italian, named after the limestone gravel turning into white dust on the famous racecourse of L'Eroica, now famous among gravel cyclists around the world. These iconic Tuscan roads boast steep climbs, fierce attacks, and breathtaking vistas, making it a must-visit for gravel cycling enthusiasts, as well as for bicycle travelers who prefer quiet, unpaved backroads.

On our self guided bike tour itinerary, you'll experience some of the routes of L'Eroica, carefully selected as part of our unpaved and gravel roads itinerary. You'll also discover the marvelous scenery, famous wines, and exquisite picturesque medieval towns that make Tuscany famous.

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  • Day 1

    Pienza & Montefollonico

    Highlights: Rennaissance Pienza, Bike fitting and test ride, Montefollonico

    Meet and greet in Pienza. Known in Italy as "the purest renaissance town", Pienza is a remarkable example of Renaissance-era town planning. If you have even the least appreciation for beautiful architecture, it is a treat to stroll around its cobblestone streets.

    For those arriving early enough in the afternoon, you can go on a test bike ride to Palazzo Massaini and Montefollonico.

    Daily Distance: 25km (15 miles) - 12 km asphalt and 13 km gravel
    Elevation Gain: +558/-565 m (+1837/-1854 ft)

    Accommodation: Relais Il Chiostro di Pienza, or similar.

  • Day 2

    Montepulciano & Bagno Vignoni loop ride

    Highlights: Val d'Orcia, Montepulciano, Monticchiello, Bagno Vignoni

    Your tour starts with a loop ride from Pienza.

    Spring brings red poppy blossoms to the vibrant green wheat fields of Tuscany, and nowhere is the bloom more brilliant than the hills of the Val d’Orcia, a UNESCO World Heritage Site. As we pedal through these corridors of proud cypress trees, the scenery may look familiar from such films as Gladiator and The English Patient. Follow the gravel tracks off the beaten path through a timeless slice of Tuscany. You'll come to hilltop Montepulciano, the jewel of southern Tuscany, full of Renaissance palaces. Enjoy the lovely, picturesque lanes of this hilltop medieval town, before setting off on a breathtaking and challenging gravel section that brings you to Monticchiello, the quintessential Tuscan hill town.

    Back in the valley, the next destination is Bagno Vignoni, a thermal spa town that dates back to Roman times. Be sure to visit the Madonna di Vita Leta chapel on the way back to Pienza.

    Daily Distance: 52km (32 miles) - 17 km asphalt and 34 km gravel
    Elevation Gain: +872/-875 m (+2861/-2871 ft)

    Accommodation: Relais Il Chiostro di Pienza, or similar.

  • Day 3

    Cycle Pienza to Montalcino

    Highlights: Pieve a Salti, the lands of Brunello wine, Montalcino, Lucignano d'asso

    To get from Pienza to Montalcino we've selected the sections of L'Eroica called Lucignano d'asso and Pieve A Salti. You leave Pienza and after 6 km of pavement, the white roads begin toward Cosona and reach the little hamlet of Lucignano - a caffe espresso at Emporio bar is a must here!

    Once you reach the paved road you ride only one km and start the other Eroica gravel section known as Pieve a Salti, where you'll be surrounded by beautiful Tuscan rural landscapes. We recommend lunch in Buonconvento, where you'll prepare for the famous climb to the famed wine town of Montalcino, a total of 10 km (half paved, half gravel) through enchanting vineyards and wineries. Once in town we suggest a visit of the hilltop fortress dominating the valleys below, where you'll be provided breathtaking views of the routes you've cycled today.

    Daily Distance: 41km (26 miles) - 17 km asphalt and 24 km gravel
    Elevation gain: +855/-807 m (+2805/-2647 ft)

    Accommodation: Hotel Giglio, Vecchia Oliviera, or similar.

  • Day 4

    Cycle to Siena

    Highlights: Castiglione del Bosco, Siena, Passo del Lume Spento

    L’Eroica—meaning “The Heroic”—is a celebration of the golden age of cycling. The event takes place every October when thousands of hardened cyclists travel back in time to ride these gravel roads on primitive machines of the past. The heavy lugged-steel bikes with down-tube shifters and impossible gear ratios are no match for the red wine in the participant’s water bottles and the racer's spirit. Today, we’ll have our own taste of cycling’s heroic origins as we join one of the most beautiful gravel sections of L’Eroica. From the heart of Brunello di Montalcino, Tuscany’s most celebrated wine region, ride to the top Passo del Lume Spento.

    Wonderful gravel cycling continues, arriving at Castiglion del Bosco, the biggest brunello winery and farm, which belongs to Ferragamo, the famous Italian fashion designer. Once in Bibbiano, you'll tackle the Piana section and and reach Murlo, another caffè stop must! Shortly you will face another legendary Eroica section to Radi, with some steep yet short ups and downs. At Ville di Corsano you deserve a light lunch. From here you have the last 12 km on secondary paved roads to marvelous Siena, one of the highlights of the tour.

    Daily Distance: 56km (35 miles) - 32 km asphalt and 24 km gravel
    Elevation gain: +1015/-1229 m (+3330/-4032 ft)

    Accommodation: Villa STR, or similar.

  • Day 5

    Gaiole in Chianti, the Eroica town

    Highlights: Gaiole, Chianti vineyards, Siena

    Today's destination is starting point of the Eroica race. After breakfast, head out into magical land of Chianti. Exiting Siena via an Eroica gravel section, making your way through wheat fields before entering the vineyards of this celebrated wine region. After reaching Pianella, you'll being a long, glourios section to Canonica a Cerreto, Vagliagli, always cycling through Chianti Classico vineyards, counting castles and old hilltop hamlets! You'll make it to Radda in Chianti for lunch time after cylcling gravel most of the day.

    From Radda, it's only 8 km to Gaiole still on the Eroica itinerary, including the breathtaking landscsapes near San Donato in Perano and Vertine.

    Daily Distance: 46km (29 miles) - 16 km asphalt and 30 km gravel
    Elevation Gain: +923/-874 m (+3028/-2867 ft)

    Accommodation: Castello di Spaltenna, or similar.

  • Day 6

    Chianti hills and Castello di Brolio loop ride

    Highlights: Chianti Senese hills, Castello di Brolio, Castelnuvo Berardenga

    On today's loop ride you'll explore the villages and hamlets of the Chianti Senese region. Start from "your" Spaltenna castle in Gaiole, reaching Castello di Brolio afer 10 km, a joyous cappuccino stop, after which you'll get on gravel sections of L'Eroica. Castelnuvo Berardenga, San Gusmé, and Villa a Sesta, are some of the small Tuscan hamlets you'll cross on today's glorious ride. On the return to Gaiole you'll have two options, including a challenging uphill to Castagnoli.

    Daily Distance: 54km (34 miles) - 44 km asphalt and 10 km gravel
    Elevation Gain: +1013/-1012 m (+3323/-3324 ft)

    Accommodation: Castello di Spaltenna, or similar.

  • Day 7

    Tour ends in Giaiole in Chianti

    Highlights: Badia a Coltibuono optional ride

    If you are feeling stronger and full of energy at this point, this morning you can tackle a 20km loop ride to Badia a Coltibuono, ending back in Gaiole where you will leave bikes. Or choose to end your tour after breakfast.

    Frequent buses to Siena are available, from where you can take fast train to your next destination.

    Daily Distance: optional 21km (13 miles)
    Elevation Gain: +395/-420 m (+1296/-1378 ft)

    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
6 nights in excellent 5-, 4- & 3-star hotels or equivalent;
All breakfasts;
Lugagge transfers;
Route notes, maps, elevation gain and city map ;
RidewithGPS App – navigation off line
Sightseeing, restaurant and shopping suggestions
Bike fitting and briefing in English by our professional staff at tour start;
Water bottle;

Not Included
Travel to and from the tour start and end;
Bicycle rental (see Prices tab);
Entrance to museums or other activities not indicated as included:
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: 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.

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Navigation and roadbook:
On this self-guided tour, detailed tour information and route navigation tracks are provided through the free smartphone app Ride With GPS, as well as a printed roadbook with thorough daily descriptions and maps.
The printed roadbook includes daily routes, maps, elevation profiles, and ride descriptions; schedules and hotel itinerary; cultural and sightseeing information, visit suggestions; emergency numbers and more. Downloading the app event 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; or rely completely on the detailed roadbook that we will print for you and deliver at tour start

On this self-guided tour, GPS device (Garmin Edge Touring) rental is available at an optional extra fee:
  • GPS device rental: €50
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    Luggage transfers are included in your package.
    The luggage is normally collected after breakfast at the reception of the hotel. 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.

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    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: itbs4235
    Countries Italy
    Begin/End Pienza / Gaiole in Chianti
    Arrive/Depart Starting point: Il Chiostro di Pienza - Corso Il Rossellino, 26, Pienza
    - The closest airports are Perugia Airport (PEG) or Florence Amerigo Vespucci Airport (FLR).

    - From Perugia Airport you can reach Perugia Train Station by Perugia Airlink Bus or taxi. From Perugia station take a train to Terontola-Cortona and then a taxi to your starting hotel. See more useful information on Trenitalia Website.
    - From Florence Airport you can reach Florence SM Novella train station by the tramway outside T2 or by taxi. See more on Florence Airport Website. From Florence Train Station, take a train to Chiusi-Chianciano Terme and then a taxi to your starting hotel in Pienza.

    *We recommend travelers plan accordingly allowing plenty of time to arrive at the determined meeting place.


    Ending point: Castello di Spaltenna - Via Spaltenna, 13 - Località Pieve di Spaltenna, Gaiole in Chianti
    - We suggest to fly out from Florence (FLR).

    To reach Florence Airport bus service available to reach Siena where you can take a train to Florence SM Novella. Take then the tramway that connects train station to airport (approximately 1h45mins travel). In alternative, you can take a taxi directly to Florence Airport (approximately 1h30mins drive)

    * If your transfers involve a taxi, 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.


    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.)

    * the hotels and prices listed above are for reference only and are subject to change (based on availability and seasonality).
    Total Distance 274-294km (170-183 miles)
    Daily Distance 25-56 km per day (15-35 miles)

    Difficulty description: Moderate to challenging over mostly hilly terrain; some steep climbs, mostly gravel or dirt, with some paved sections. You'll be mostly on secondary backroads, although you may share the road with car traffic in short stretches. Appropriate for cyclists who are comfortable with gravel and dirt road cycling.

    Please note that all distances are approximate. Due to circumstances that may be beyond our control, weather conditions or provisions issued by local authorities, the itinerary may be subject to some changes before and/or during your holiday. For example, along the way you may find temporary deviations/detours caused by roadwork, In this case, please follow the directions posted on site

    Rating 301
    Notes This tour is part of our Partner Tours Collective program: operated by select local partners that we know and trust, the tour is similar in quality to those we operate directly in many ways. Please click here for more details.
    Terms Terms & Conditions
    Dates Prices Single Supplement
    Dates This tour is available everyday from March 29 to November 3
    Not available from July to the last week of August, and from September 29 to October 2

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

    Tour can depart any day of the week.

    Solo traveler departures are also available (only one person on the departure) on request.

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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 Pienza and collection from ending point in Gaiole.

    Bike rental rates
    Gravel bike: €250
    E-bike: €250

    For more information on bikes available for this tour, please see Tuscany Gravel Bikes
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    Are you looking for other Tuscany itineraries? Check out our lower-difficulty level Tuscany Tours: Classic Tuscany 8-day Bike Tour and Postcard Southern Tuscany 8-day Bike Tour. ________________________________________

    Additional useful information:

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

    • If the self-guided formula isn't right for you, check out this blog introducing the differences between Guided and Self-Guided Tours.
    Prices €1690 per person* Single Supplement €560 fee (in double room for single use)*
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