Gravel Explorer: White Roads of Tuscany

White Roads of Tuscany
  • Length 7 days
  • From USD$3295
  • Style/Level Gravel Explorer 3.5
  • Countries Italy
  • Begin/End Siena/Cortona

In 1997, 92 cyclists pedaled out of Gaiole in Chianti, to protest the paving of Tuscany’s white gravel roads, or strade bianche. Now an annual event, L’Eroica celebrates pure cycling joy and has inspired the development of this stunning tour among the white roads of Tuscany. Ride romantic and famed winding cypress-lined roads, visit hilltop towns, and immerse yourself in one of the most photographed areas of Italy – the Val d’Orcia, a UNESCO World Heritage designated landscape. Highlights include the Renaissance and Medieval towns of Siena and Cortona, riding through small, medieval Tuscan villages, or “borgos”, and thermal spa towns, and enjoying iconic views everywhere you look. Your pace will be slower on Gravel Explorer tours since riding on dirt is slower than on the road (but like all Gravel Explorer tours, the route is a mix of off pavement and paved). If you are used to riding on gravel, you’ll love these routes. If you are new to gravel, this is a great way to see if you have a taste for it!

Learn more about our Gravel Explorer Tour Styles at the webpage at this link!

Highlights

  • The famed white roads of Tuscany

  • Vineyards of Montalcino

  • Siena and its beautiful piazza

  • Picture perfect Pienza

  • Val d’Orcia – a UNESCO World Heritage Cultural Landscape

  • Roman spa towns

  • Hidden villages

Includes

  • 6 nights, 7 days. All breakfasts, meals as noted in itinerary, use of a bicycle (there is a surcharge on e-bikes). Full van support, GPS on your bike for navigation.

  • All Gravel Explorer tour inclusions

Keep in mind

We work hard to maintain consistency across all of our tours, but some trips have unique differences. Here are some things to keep in mind about this tour.

  • This tour spends time on and off paved roads so support van and aid may not always be readily available. You will have the option to pedal with a guide or on your own. If you opt to cycle on your own we recommend you are comfortable being independent. 
  • Navigation, hotels, meals? Learn more about what is included and what to expect on your Gravel Explorer tour. 
  • If you are interested in using a gravel bike for this tour, we outfit our road and e-road bikes with wider, knobbier tires.

Consider that around 50% of the ride will be on gravel or hard packed dirt roads which may have sections with washboard or rougher terrain. Your pace will be slower and the perceived effort will be greater than when you are on pavement.


Date Price Private room fee Note
Sep 7-13, 2025 USD$3295 USD$450 Departure confirmed to go!   
Oct 5-11, 2025 USD$3295 USD$450
DateSep 7-13, 2025
PriceUSD$3295
Private room feeUSD$450
NoteDeparture confirmed to go!   
DateOct 5-11, 2025
PriceUSD$3295
Private room feeUSD$450
Note

Download Itinerary

We’ll send you a link to a full day by day tour itinerary that can be downloaded and printed so you can review all the details online and offline. This packet also includes details about what to expect on tour and arrival and departure details.
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  • Total distance 232km (144 miles)
  • Average daily distance 46km (29 miles)
  • Tour style Gravel Explorer
  • Tour level 3.5

Highlights: Piazza del Campo, the majestic Duomo, and a maze of medieval tiny alleys

Arrive today in our centrally located hotel and start to explore the city of the Palio – a storied, annual horse race that brings locals and tourists out alike. Siena, once a fierce rival of Florence, has kept much of its medieval atmosphere and traditions alive. A walk through town cannot miss the main square Piazza del Campo where the Palio is held.

Meals : Dinner
Lodging : Hotel Athena

Highlights: Eroica white roads, Crete Senesi hills, iconic cypress views, Buonconvento

Start from Siena and head towards the spectacular “Crete Senesi,” or badlands of Tuscany, on the white roads of the famous Eroica race. Pedal through hidden hamlets and medieval Tuscan villages as you cycle the Arbia Valley on your way to the walled village of Buonconvento, a prominent destination on the Via Fracigena, a pilgrimage route from Canterbury, England to Rome. 50% unpaved.

Meals : Breakfast, Dinner
Lodging : Hotel Albergo Ghibellino

Highlights: Via Fracingena, Asso River Valley, cypress-lined roads, and Montalcino

Leave Buonconvento on a great stretch of the famous Eroica route toward the Asso River Valley. Amazing views open over the Crete hills and their farms as you continue to Torrenieri. Cycle among the Brunello vineyards as we climb to the famous hilltop village of Montalcino. 55% unpaved.

Meals : Breakfast
Lodging : Hotel dei Capitani

Highlights: Brunello di Montalcino vineyards, Lucignano d’Asso, Eroica roads, Pienza

More rolling white roads lead us through the vineyards of Brunello di Montalcino on our way to Pienza. Enjoy the views as we ride through little castles and medieval properties that have been converted into world famous wineries. Our destination is Pienza. In 1996 UNESCO declared the town a World Heritage Site and in 2004 the surrounding Val d’Orcia, was included on the list of UNESCO’s World Cultural Landscapes. 65% unpaved.

Meals : Breakfast
Lodging : Relais Il Chiostro di Pienza

Highlights: Pienza, Bagno Vignoni San Quirico, Vitaleta Chapel

Today is for immersing yourself in the Unesco World Heritage cultural landscape of the Val d’Orcia. You’ll ride ‘strada bianche’ lined with cypresses, explore the town of San Quirico, enjoy stunning Bagno Vignoni with its hot springs, and stop by the most iconic place in Tuscany, Vitaleta Chapel, before returning to Pienza. 54% unpaved.

Meals : Breakfast
Lodging : Relais Il Chiostro di Pienza

Highlights: Montefollonico, vineyards of Montepulciano, the Chiana Valley, Cortona

Our final ride takes us beyond Val d’Orcia were our beloved white roads takes us into wooded forests. Sudden fortified hilltop villages delight us with exceptional vistas over the valleys and Montepulciano vineyards. Glide down gentle hills all the way into the Chiana valley and our last night’s stay in Cortona. 43% unpaved.

Meals : Breakfast, Dinner
Lodging : Hotel San Luca

Highlights: Medieval town center, the Etruscans Museum

The tour ends in Cortona. This town offers more gems to be discovered! Stay on, explore more of Tuscany, or head to Rome.

Meals : Breakfast

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



Pre-trip planning checklist

Italy travel planning page



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