Get ready, cyclists: this one's for you! The Eroica is a world-renowned vintage bike race, held annually in the hilly, vineyard-dotted region of Chianti in Tuscany. Follow the route of this legendary race, experiencing the Strade Bianche (unpaved white roads) that take you through the heart of this magnificent countryside.


  • Explore UNESCO-recognized Siena
  • Cycle through vineyards and olive groves
  • Visit hilltop towns with ancient, sprawling fortress walls
  • Try a glass of the famed Brunello wine

Brief Itinerary

Day Highlights Overnight
Day 1 Siena Siena
Day 2 Siena to Buonconvento Buonconvento
Day 3 Montalcino and the local Brunello Buonconvento
Day 4 Buonconvento to Castelnuovo Castelnuovo
Day 5 Castelnuovo to Radda Radda
Day 6 Radda to Siena Siena
Day 7 Departure  

Detailed Itinerary

Day 1: Welcome to Siena

Siena's famed main square
Siena's famed main square

Welcome to Siena - a UNESCO World Heritage Site in the heart of Italian wine country. Spend your first day here exploring the cobbled alleyways, stopping into the town's many museums, and, of course, visiting the spacious central square (Piazza del Campo) where the famed Palio de Siena bareback horse race runs several times a year.

Day 2: Cycling Siena to Buonconvento

Buonconvento: one of Italy's most beautiful villages
Buonconvento: one of Italy's most beautiful villages

Your first day's ride will launch you straight into the typical rolling countryside of the Chianti region, where ancient brick walls are grown over with roses, vineyards tumble down hills, and olive groves line dusty lanes. After a relatively easy ride, you'll arrive in one of Tuscany's most reputed wine regions for a stay in a countryside agriturismo with a swimming pool. Dinner is fresh and local, made with local products and olive oil grown right here at the agriturismo itself. 

Cycle distance: 25 miles (40km)

Day 3: Cycling to hilltop Montalcino

Wine cellar in Buonconvento
Wine cellar in Buonconvento

Today's ride is a loop beginning and ending in Buonconvento - one of the most beautiful villages in Tuscany according to the I Borghi più belli d'Italia Club. Cycle from Buonconvento to Montalcino, where the famed Eroica cycle race culminates in an altitude of nearly 2,000 feet (600m). The town sits pretty on the hilltop with a historic abbey at its peak and ancient walls surrounding it. Reward yourself with a glass of the famous Brunello di Montalcino wine and then circle back to your agriturismo for another night of homemade Italian cuisine.

Cycle distance: 37 miles (60km).

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Day 4: Cycling Buonconvento to Castelnuovo


Wave farewell to Buonconvento as you mount your bike and make your way to charming Asciano on the famed white streets of the Strade Bianche. Pause at the charming Santa Maria Abbey of Monte Oliveto Maggiore and the Church of Saint Agathe before continuing up a series of small climbs and sharp descents to the villages of Castelnuovo Berardenga. Stop here for a night surrounded by vineyards.

Cycle distance: 29 miles (46km).

Day 5: Cycling Castelnuovo to Radda in Chianti

Hilltop town of Radda
Hilltop town of Radda

Get ready for a day of climbing! Your next stop - the charming, characteristically Italian hilltop town of Radda in Chianti - is perched at 1,640 feet (500m). Once you arrive, make time to explore the magnificent fortified village (inhabited since the 9th century!) and take plenty of photos of the postcard-perfect countryside of vineyards and olive groves spread out below the town.

Cycle distance: 22 miles (35km).

Day 6: Cycling Radda in Chianti to Siena

Siena, Italy
Siena, Italy

Spend your last cycling day circling back to photogenic, popular Siena, alternating between tiny country lanes and bright white Strade Bianche. Today's ride is an easy one full of magnificent scenery - a perfect way to end a satisfying cycling trip. If you haven't already explored Siena's cathedral, the Biblioteca Piccolomini library, the Torre del Mangia tower, or the crypt under the Duomo, today's your day.

Cycle distance: 25 miles (40km).

Day 7: Farewell Tuscany!

Italian bruschetta
Italian bruschetta

After breakfast, it's time to wave farewell to famous Siena and make your way back home. If you have some extra time in Italy, the pink-stoned, religiously significant hilltop town of Assisi, the thermal spas of Tuscany, and the foodie-loved region of Emilia-Romagna are just a hop, skip, and jump away.


Map of Riding the Eroica Among Famous Vineyards in Tuscany - 7 Days
Map of Riding the Eroica Among Famous Vineyards in Tuscany - 7 Days