Day 1: Arrive in Florence Spend the day exploring the city, soaking in the Renaissance art and architecture. Consider renting a bike to explore the city’s narrow streets and alleys.

Day 2: Florence to Greve in Chianti (approx. 40 km) Cycle through the Chianti wine region, passing through picturesque vineyards and olive groves. Stop in the hilltop town of Impruneta to see the famous terracotta works and enjoy a coffee. Arrive in Greve in Chianti and sample some of the region’s famous wines.

Day 3: Greve in Chianti to Siena (approx. 70 km) Cycle through the heart of Tuscany, passing by classic Tuscan villas, farms, and rolling hills. Stop in the charming town of Radda in Chianti for a coffee and a pastry. Arrive in Siena, a UNESCO World Heritage site with a stunning Gothic cathedral and a vibrant historic center.

Day 4: Siena to Montalcino (approx. 70 km) Cycle through the hills of the Crete Senesi, a landscape of clay hills, cypress trees, and fields of wheat. Visit the medieval walled town of Buonconvento, then continue on to Montalcino, known for its famous Brunello wine.

Day 5: Montalcino to Pienza (approx. 45 km) Cycle through the Val d’Orcia, a UNESCO World Heritage site and one of the most scenic areas of Tuscany. Visit the hilltop town of San Quirico d’Orcia and the stunning abbey of Sant’Antimo before arriving in Pienza, a charming town known for its pecorino cheese.

Day 6: Pienza to Montepulciano (approx. 25 km) Cycle through the gentle hills of the Val d’Orcia to the town of Montepulciano, known for its Vino Nobile wine. Visit the Renaissance palaces and churches in the town, and enjoy a glass of wine.