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. 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 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 San Gimignano San Gimignano
Day 2 San Gimignano - Siena Siena
Day 3 Siena - Buonconvento Murlo
Day 4 Buonconvento - Montalcino Murlo
Day 5 Goodbye Tuscany  

Detailed Itinerary

Day 1: San Gimignano

Tuscany, Italy
Tuscany, Italy

Arrive in San Gimignano and explore the town of many towers, which is a remarkable example of Tuscan medieval architecture. The towers were once significant as families built them as symbols of their wealth and power. Today you can climb the ruins for beautiful countryside views. The town is also known for its particular white wine — Vernaccia di San Gimignano — which you can taste as part of your exploration.

Day 2: San Gimignano - Siena

Duomo di Siena, Italy
Duomo di Siena, Italy

Your exploration of the Tuscan countryside will continue as you make your way from San Gimignano to Siena 26 miles (42 km) south by bike, winding through picturesque roads and vineyards. You might stop for wine tasting to take a breather, before arriving in Siena where you can people watch in the Piazza del Campo.

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Day 3: Siena - Buonconvento

Tuscany, Italy
Tuscany, Italy

The area of the Crete Senesi, in the Province of Siena, is your backdrop for the day. The land is known for its gray soil and forests that are rich in truffles. You'll make your way to Murlo, traveling 26 miles (42 km) south. For a break from the saddle, your first stop will be the village of Buonconvento — a popular stop for travelers along the Via Francigena pilgrimage route.

From there, you'll reach Murlo — a medieval village surrounded by walls — on the way to the farm where you will spend the night. You can have a leisurely afternoon swimming in the pool during summer months, get a massage, or enjoy the sauna in colder months, after a full day on the road.

Day 4: Buonconvento - Montalcino

Montalcino, Italy
Montalcino, Italy

Get ready for a steep climb ahead, as you travel from Murlo to Montalcino, a distance of 28 miles (46 km). In Montalcino, which is known for its Brunello wine, you can sip on vintages as a reward for your efforts. After a relaxing afternoon, you'll have an exhilarating descent to your farmhouse, where you can rest for the evening.

Day 5: End of tour

Tuscan wine
Tuscan wine

After breakfast, you'll have a transfer to Buonconvento train station, where you'll make your way home or on to your next destination. 


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