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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

These white, dusted roads are home to one of pro racing’s biggest dates, with steep climbs and full-blown attacks at every bend.
The Strade Bianche of Tuscany is truly something special due to the region’s rolling vistas and fine wines make this a must-see destination if you love gravel cycling. Strade bianche is Italian for “white roads,” and it comes from the color of the dry limestone gravel that lifts into a fine white dust that lingers along the race course.
Discover the route of the Strade Bianche professional race .
In this self guided Bike Tour we selected the more appropriate unpaved sections from the race and also from the Eroica itinerary.
The Permanent Route of L’Eroica is a unique experience that allows you to live the adventure of L’Eroica all year round. Anyway we offer the tour from March to November.
Traditional L’Eroica course starts in the town of Gaiole and covers some of the most beautiful roads in the area of Chianti and Siena province, winding among historic vineyards, leading to the cypress-lined entrance of Castello di Brolio and Corte Pavone.
Quote from the Eroica home page “L’Eroica invite cyclists to rediscover the beauty of fatigue and the thrill of conquest. We look to the past of cycling to inspire the future of this beautiful sport”

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  • Day 1

    Pienza & Montefollonico

    Highlights: Welcome to Pienza, Bike Fitting, Test Ride, Montefollonico

    Meet & Greet in Pienza, the purest renaissance town in the world, for welcome and bike fitting. Pienza the “perfect town” 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.
    If you arrive in time there will be a First test bike ride to Palazzo Massaini, 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

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

    Your tour starts with a circular 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 Montepulciano, the jewel of southern Tuscany, full of Renaissance palaces. After relaxing a while, you will face a incredible breathtaking yet challenge gravel section that bring you to Monticchiello, the quintessential Tuscan hill town.
    Back in the valley, next destination is Bagno Vignoni, a thermal spa town that dates back to Roman times, Madonna di Vita Leta chapel is 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

    Pieve a Salti to Brunello Land

    Highlights: Pieve a Salti, Brunello Land, Montalcino, Lucignano d'asso

    To get from Pienza to Montalcino we select the sections of Eroica called Lucignano d'asso and Pieve A Salti. You leave Pienza and after 6 km on paved road you will take with white road toward Cosona and reach the little hamlet of Lucignano - a caffe espresso at little shop emporio - is a must. Once you reach the paved road you ride only one km and start the other Eroica gravel section Pieve a Salti - so beautiful landscape. 9 km up and down in the rural countryside! Arrive in Buonconvento by lunch time. Now you have to face the climb to the famed wine town of Montalcino. A total of 10 km: 5 on paved and 5 km on gravel all through vineyards and wineries. Once in town we strongly suggest to visit the fortress and admire the breath-taking view of the entire valley you've just biked.

    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

    Castiglione del Bosco & 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 hardman mentality. 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. In fact starts the Castiglion del bosco gravel section. Castiglion del bosco is the biggest brunello winery & farm belonging to Ferragamo, the famous Italian fashion designer. Once in Bibbiano another section called la Piana and reach Murlo after 30 km- caffé & visit! Shortly you will face another legendary Eroica section to Radi, with some steep yet short up and down. At Ville di Corsano you deserve a light lunch. From here you have the last 12 km on secondary paved road to Siena.

    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, the Eroica town

    Highlights: Gaiole, Chianti vineyards, Siena

    Today the destination is the town where the Eroica starts.
    After your gourmet breakfast, head out into magical Chianti. You will exit form Siena via a eroica gravel section Pieve a Bozzone, Vico dArbia making your way through wheat fields before we hit the vineyards of this celebrated wine region. Reach Pianella after 15 km. Form here you will take a long glourios section to Canonica A Cerreto, Vagliagli. All riding through chianti classico vineyards, counting castles and old hilltop hamlets! Get in Radda in Chianit for lunch time after 38 km ride - mostly gravel.
    Relax... you have only 8 km to Gaiole following still the Eroica itineray.
    Last gravel stage: San Donato in Perano and Vertine are amazing, enjoy the breathtakign landscape.

    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 - Castello di Brolio

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

    Today is consacrated to explore all the villages and hamlet of Chianti Senese. Start from your "castle di Spaltenna" in Gaiole and reach Castello di Brolio afer 10 km. Here the caffe at agribar in front of winery is a must: all cyclists, locals and visitors seems to meet there.
    After you can ride into the gravel section of Eroica, is short and then you will ride on very secondary scenery roads until Castelnuvo Berardenga. It worth a visit and if you are there for lunch time offer many options. Back to the saddle and encounter other small borgo: San Gusmé and villa a Sesta. Back to Brolio: to return to Gaiole you have 2 options, one road downhill and flat so somewhat easy, or challenge uphill to Castagnoli, downhill to castello di Meleto.

    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, Gaiole, Goodbye, Arrivederci

    If you still have energy and feel your legs stronger you can have a short ride to Badia a Coltibuono (20km loop).
    Back to Gaiole where you will leave bikes.

    Departure: bus available to reach Siena where you can take fast train to other town

    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;
Access to smartphone app with tracks and digital roadbook;
Printed roadbook (A5 format)
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.


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
  • ________________________________________

    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.


    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 0 to 56 km per day (0 to 35 miles)

    Difficulty description: Moderate to Challenge over mostly terrain, with moderate to challenge daily mileage; scenic routes; genuine experiences of Tuscan Italian life and culture.
    Rating 101 to 201
    About Tour Ratings »
    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 April 1 to October 31

    2024 pricing coming soon!

    Tour can depart everyday.

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

    **Please note that all distances are approximate. Due to circumstances beyond 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


    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

    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 €1590 per person* Single Supplement €560 fee (in double room for single use)*
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