Tuscany Gravel - The White Roads of L'Eroica

Bike - Self-Guided Tour

7 days
€ 1690
Bike - Self-Guided Tour
3
Italy
Pienza/Gaiole in Chianti

Overview

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.

Highlights

  • Cycle the white gravel roads of L’Eroica, the famous vintage bike race
  • Taste superb Tuscan wines in ancient cellars
  • Pienza, the perfect Rennaissance city
  • Stunning Tuscan countryside
  • Montalcino, Montepulciano
  • The Chianti hills
  • Majestic Siena

Daily itinerary

7 days
284 km (177 miles) 
30-60 km (18-37 miles) 
3

Day 1 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: 30 km (18 miles) - 18 km asphalt and 12 km gravel
Elevation Gain: +558 m (+1837 ft)
Terrain type:

Accommodation: Relais Il Chiostro di Pienza, or similar.

Day 2 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) - 26.5 km asphalt and 25 km gravel
Elevation Gain: +872 m (+2861 ft)
Terrain type: hilly

Accommodation: Relais Il Chiostro di Pienza, or similar.
 

Day 3 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: 42 km (26 miles) - 22 km asphalt and 20 km gravel
Elevation gain: +855 m (+2805 ft)
Terrain type: hilly

Accommodation: Hotel Giglio, Vecchia Oliviera, or similar.

 

Day 4 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: 59 km (35 miles) - 37 km asphalt and 22 km gravel
Elevation gain: +1015 m (+3330 ft)
Terrain type: hilly

Accommodation: Villa STR, or similar.

 

Day 5 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: 47 km (29 miles) - 27 km asphalt and 20 km gravel
Elevation Gain: +923 m (+3028 ft)

Accommodation: Castello di Spaltenna, or similar.

Day 6 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: 55km (34 miles) - 50 km asphalt and 5 km gravel
Elevation Gain: +1013 m (+3323 ft)
Terrain type: hilly

Accommodation: Castello di Spaltenna, or similar.
 

Day 7 Day 7 - Tour ends in Giaiole in Chianti

Highlights: arrivederci!

Your tour ends after breakfast.

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

PLEASE NOTE: The final itinerary, including hotels and/or activities described here, are subject to changes according to availability. 

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. 

Visit our Tour difficulty level page to learn more about terrain levels and how we determine day and tour levels.

 

 

Map

What's included

  • 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

Optional activities

  • Montalcino and Gaiole in Chianti winery tour and tasting
  • Pienza cooking lesson with lunch
  • Podere Casale dairy farm cheese tasting

Dates and availability

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

Tour can depart any day of the week.

2025 confirmed departures
Coming soon (please inquire!)

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Prefer a Tuscany itinerary on paved roads? Check out our lower-difficulty tours Classic Tuscany 8-day and Postcard Southern Tuscany 8-day.


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Tour Code: itbs4235


Partner Tours Collective 

Since we cannot directly operate self-guided tours everywhere, we use our vast network in the continent to curate and offer tours operated by select local partners that we know and trust. These tours are similar in quality to those we operate directly – for example, they usually begin with an in-person briefing and bike fitting (with English-speaking local staff); bicycles are provided in optimal condition; the roadbook and navigation instructions, as well as lodging are of similar quality, as well as the routes and inclusions.

Prices

Price €1690

Prices per person, based on double occupancy; minimum 2 participants per departure.

Single supplement: € 560 (in double room for single use).

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

Lodging upgrades & extra nights are available: please inquire.

City hotel tax not included in tour package  (2 to 5 euro per night per person, to be paid locally by traveler).
* due to the 2025 Rome Jubilee, some cities may charge a higher per night tax

On this self-guided tour, GPS device (Garmin Edge Touring) rental is available at an optional extra fee:
GPS device rental: €50

Group Discounts are available for participants booking together on the same departure! Please inquire!

For more ways to save, see our discounts and promotions page. 

 

Bike rental

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 Bologna and collection from ending point in Parma.

Bike rental rates

Gravel bike: €250
E-bike: €250

For more information on bikes available for this tour, please see Tuscany Gravel Bikes

Trip planning

Starting point

 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

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.)

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