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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 plus riding through small, medieval Tuscan villages, or “borgos”, thermal spa towns, and stunning views everywhere you look. Days are longer on Gravel Explorer tours since the going 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

  • Cycle the famed white roads of Tuscany, the vineyards of Montalcino, Siena and its beautiful piazza, the Val d’Orcia – a UNESCO World Heritage Cultural Landscape with its picture perfect vistas, Roman spa towns, hidden villages, winding gravel roads with views for miles from the top.

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 pedal on your own, but please be aware that if you are cycling on your own we recommend you are comfortable cycling in remote areas. 
  • 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, more knobby tires. The frame geometry of the bike is ideal for gravel touring.

Consider that around 50% of the ride will be on gravel roads and roads sometimes with rough 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
Apr 28-May 4, 2025 USD$3295 USD$450 Book by November 1st and save $200 per person.
Book it
Sep 7-13, 2025 USD$3295 USD$450 Departure confirmed to go! Book by November 1st and save $200 per person.  
Book it
Oct 5-11, 2025 USD$3295 USD$450 Book by November 1st and save $200 per person.
Book it
DateApr 28-May 4, 2025
PriceUSD$3295
Private room feeUSD$450
NoteBook by November 1st and save $200 per person.
Book it
DateSep 7-13, 2025
PriceUSD$3295
Private room feeUSD$450
NoteDeparture confirmed to go! Book by November 1st and save $200 per person.  
Book it
DateOct 5-11, 2025
PriceUSD$3295
Private room feeUSD$450
NoteBook by November 1st and save $200 per person.
Book it

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 230km (140 miles)
  • Average daily distance 45km (28 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 historical and traditional horse race that brings locals and tourists out alike. Siena, once a fierce rival of Florence, has kept much of its medieval atmosphere. 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, cypres iconic 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. 50% unpaved.

Meals : Breakfast, Dinner
 Lodging : Hotel Albergo Ghibellino

Highlights: Iconic Tuscan cypress views of the Val d’Orcia, Montalcino vineyards

Today’s loop ride explores the Asso Valley and the imposing Abbey of Monte Oliveto Maggiore. Amazing views open over the Crete hills and their farms as you continue to Torrenieri. Cycle among the Brunello vineyards as we pass at the base of famous hilltop village of Montalcino on our way back to Buonconvento. 30% unpaved.

Meals : Breakfast
 Lodging : Hotel Albergo Ghibellino

Highlights: Iconic Tuscan cypress views of Valdorcia, Montalcino vineyards, Lucignano d’Asso, Eroica roads, Pienza

More Eroica white roads leads us through the vineyards of Brunello di Montalcino. Enjoy the views as we ride through little castles and medieval properties that have been converted into world famous wineries. Our destination today is Pienza, in the heart of the Unesco World Heritage Val d’ Orcia. 70% 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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