Tuscany is famous for its beautiful landscapes, vineyards, cypress trees, farms, and medieval hill towns. What better way to experience some of the best views in Italy than by bike? With this brief but immersive five-day itinerary, you'll explore the hills and towers of San Gimignano, have a chance to taste Brunello wines in Montalcino, and learn about the history and architecture of Siena.


  • Soak up views of the Tuscan countryside from the seat of your bicycle
  • Marvel at the hills and towers of San Gimignano
  • Sip some of the best wines in Italy in Montalcino
  • Explore the winding streets and learn about the history of Siena

Brief Itinerary

Day Highlights Overnight
Day 1 Arrive in San Gimignano, Cycle in the Chianti Hills San Gimignano
Day 2 Cycle to Siena, Tuscany's Medieval Treasure Siena
Day 3 Cycle to Murlo via Buonconvento & the Crete Senesi Murlo
Day 4 Cycle to Montalcino& the Val d'Orcia Murlo
Day 5 Depart Buonconvento  

Detailed Itinerary

Day 1: Arrive in San Gimignano, Cycle in the Chianti Hills

Tuscany, Italy
Settle into hilltop San Gimignano and warm up with a cycle around the surrounding countryside

Benvenuti in Toscana! Start your biking tour in San Gimignano, a UNESCO World Heritage Site whose entire town is a testimony to enchanting medieval architecture and its many torre (towers) that have survived through the centuries. Start with a pedal through the nearby Chianti Hills. The rolling landscape is dotted with picturesque villages and vistas of vineyards and cypresses—perfect for a gentle warm-up on your first day. Return to San Gimi (as it's known to locals) in the late afternoon and relax with a glass of the local Vernaccia di San Gimignano before heading out to dinner.

Day 2: Cycle to Siena, Tuscany's Medieval Treasure

Cycle to Siena
Relax with a cool drink in Piazza del Campo after a day in the saddle

Rise and shine for another epic day of cycling in the Tuscan hills. Today's 26-mile (42 km) route from San Gimignano to the walled city of Siena takes in plenty of vineyards and fields laden with sunflowers. You'll wind through undulating hills and ride along countryside dotted with medieval castles, villages, and churches. With several opportunities to stop at local wineries along the way, choose whether to take your time (and sample the local vintages) or head straight to Siena's Piazza del Campo. Relax, and people watch over an Aperol spritz before settling in for dinner at a local restaurant.

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Day 3: Cycle to Murlo via Buonconvento & the Crete Senesi

Savor the views with a gentle spin through the Crete Senesi

Tuscany's Crete Senesi lies southeast of Siena and is rich cycling territory with plenty of strade bianche, the famous unpaved "white roads" that wind through the countryside and take in some of the region's most beautiful views. Your destination is Murlo, a medieval walled village nestled among the rolling hills. Take a break from the saddle on today's 26-mile (42 km) route and pause for refreshments at Buonconvento, a village popular with travelers (and cyclists) along the historic Via Francigena pilgrimage route. 

When you're ready, carry on to your agriturismo (boutique farmhouse) in Murlo. In the summer months, make the most of the pool (or, in the cooler months, the sauna) and enjoy an afternoon of downtime after a day on the bike. Spend the evening relaxing with a glass or two of the local wine and homemade Tuscan fare. 

Day 4: Cycle to Montalcino & the Val d'Orcia

Cycling in Tuscany
Get back in the saddle for today's ride to Montalcino

Fuel up this morning with caffè and a cornetto (croissant) for your final 28-mile (46 km) ride to the gorgeous hilltop town of Montalcino. There's a steep climb or two as you set out southeast through the Val d'Orcia, home to some of Tuscany's loveliest countryside with views of the region's iconic cypress trees.

Arrive at Montalcino and reward your efforts with a glass of the town's famous Brunello di Montalcino and a bite to eat at one of the local bars. After a relaxing afternoon, enjoy the exhilarating descent back to your agriturismo, where you'll spend another night and toast the end of your cycling adventure. 

Day 5: Depart Buonconvento

Goodbye Italy
Salute! Raise a toast to your Tuscan adventure

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

More Great Italy Itineraries

Looking for more inspiration for your trip to Italy? Check out these other Italy itineraries, explore different ways to spend five days in Tuscany, or discover the best time to visit Italy.


Map of Tuscany By Bike: San Gimignano, Siena & Murlo - 5 Days
Map of Tuscany By Bike: San Gimignano, Siena & Murlo - 5 Days