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. With a week to spare, you can follow the route of this legendary race, experiencing the "strade bianche" (unpaved white roads) that take you through the heart of this magnificent countryside. Between epic rides, you'll spend your free time strolling through hilltop medieval villages, sampling the local wines, and relaxing at peaceful agriturismos.


  • Cycle the Eroica, a famed route along Tuscany's "strade bianche"
  • Visit the hilltop towns of Montalcino and Siena
  • Dine on regional dishes, sip Tuscan wines, and stay in a traditional farmhouse

Brief Itinerary

Day Highlights Overnight
Day 1 Arrive in Siena, Explore Siena
Day 2 Cycle to Buonconvento, One of Italy's "Most Beautiful Villages" Buonconvento
Day 3 Cycling Loop to Medieval Montalcino Buonconvento
Day 4 Cycle through the Crete Senesi to Castelnuovo Berardenga Castelnuovo
Day 5 Cycle to the Ninth-Century Village of Radda in Chianti Radda in Chianti
Day 6 Cycle Back to Siena Siena
Day 7 Depart Siena  

Detailed Itinerary

Day 1: Arrive in Siena, Explore

Siena's famed main square
Siena's famed Piazza del Campo has long been popular with cycling tours and races

Bienvenuti in Toscana! Start your cycling tour in Siena, a UNESCO World Heritage Site known for its Gothic history, art, and the famed Palio horserace. The surrounding Terre di Siena landscape is at the heart of the Tuscan L'Eroica cycle race, passing through Chianti, the Crete Senesi, and the cypress-filled Val d'Orcia. Spend your first day exploring Siena's boutique-filled narrow streets, stroll the historic Piazza del Campo, and linger over lunch at a neighborhood trattoria. Or warm up the legs with a spin around the picturesque hilltop villages before settling in for aperitivo in the square.

Day 2: Cycle to Buonconvento, One of Italy's "Most Beautiful Villages"

Set off for a spin on Tuscany's famed strada bianche
Set off for a spin on Tuscany's famed strada bianche

Launch straight into the mesmerizing landscape of the Chianti region with today's 25-mile (40 km) ride to Buonconvento, one of Italy's famed I Borghi più belli d'Italia, an association of Italy's most beautiful and notable villages. It's a relatively easy cycle winding along the region's unpaved strade bianche (white roads) through hills dotted with vineyards and olive groves. Reach your farmhouse and enjoy typical Italian agriturismo (agritourism) hospitality with a warm welcome from your hosts and a delicious dinner with fresh produce and olive oil directly from the farm. 

Day 3: Cycling Loop to Medieval Montalcino 

Visit the hilltop town of Montalcino on today's climb

Today's ride is a 37-mile (60 km) loop beginning and ending in Buonconvento with a stop in Montalcino, where the Eroica cycle route culminates at an altitude of nearly 2,000 feet (600 m). It's also home to the renowned Vino di Brunello di Montalcino vineyards. After winding through hills dotted with medieval castles and churches, stop for lunch in the town and reward your efforts with a glass of the famed red wine. Circle back to your agriturismo for a cool down in the pool before another feast of home-cooked Tuscan fare. 

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Day 4: Cycle through the Crete Senesi to Castelnuovo Berardenga

Savor the views on today's ride across the Crete Senesi

Fuel up on caffè and a decent breakfast this morning before setting off for Castelnuovo Berardenga, nestled within the rolling Chianti Hills and the strade bianche-strewn landscape of the Crete Senesi. Start the 29-mile (46 km) route with a pedal over to charming Asciano and pass the Abbazia di Monte Oliveto Maggiore. This beautiful redbrick Benedictine monastery stands out against the backdrop of the Crete Senesi's weathered chalk cliffs. Continue up a series of small climbs and sharp descents until you reach your agriturismo surrounded by vineyards. 

Day 5: Cycle to the Ninth-Century Village of Radda in Chianti

Go for a spin in the hills around Radda in Chianti
Go for a spin in the hills around Radda in Chianti

Get ready for a day of climbing! Today's route takes you 22 miles (35 km) southwest to the picturesque hilltop town of Radda in Chianti. Perched at 1,640 feet (500 m), the striking fortified village is worth the extra effort when you reach the top. Stop for a bite to eat and a cool drink before exploring the historic streets—the village has been inhabited since the ninth century. Check into your accommodation, and when you're ready, head out for dinner. The town is known for its excellent cuisine, and you'll find plenty of great dining spots serving authentic Tuscan fare. 

Day 6: Cycle Back to Siena

Siena, Italy
Take the weight off with a spritz in Siena's central piazza

Spend your last cycling day circling back to Siena, alternating between tiny country lanes and bright-white strade bianche. Today's 25-mile (40 km) ride is an easy one, full of magnificent Tuscan scenery. Arrive in Siena's main plaza and toast your week's efforts with a spritz or glass of the local Chianti. Spend the afternoon touring any sights you haven't had a chance to see. Don't miss the Duomo di Siena, a magnificent Romanesque-Gothic cathedral known for its intricate marble inlay floor and treasures, including works by Bernini, Pisano, and Donatello. 

Day 7: Depart Siena

A la prossima, Strade Bianche!
A la prossima, strade bianche!

It's time to bid arrivederci to Tuscany this morning and part ways with your bike. Your driver will take you to the train station or airport in time to make your flight or continue your European adventure. Safe travels!

More Great Italy Itineraries

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Map of Cycle the Eroica Among Tuscany's Famous Vineyards - 7 Days
Map of Cycle the Eroica Among Tuscany's Famous Vineyards - 7 Days