Cycling Holidays in Tuscany & Chianti

• Pedal the winding Tuscan roads of Chianti & Montepulciano
• Marvel at the Renaissance architecture in the cities of Pisa, Lucca and Florence
• Explore the vineyards of Chianti and sample the iconic Chianti Classico wines
• Discover the hill top villages, picturesque olive groves and vineyards
• Treat yourself to gelato in the buzz of Siena’s Piazzo del Campo
• Enjoy wonderful hospitality along with delicious Italian food and wine

Immerse yourself in Tuscany, surely one of Italy's most iconic regions, on a self-guided cycling holiday. Tuscany is a culmination of world-famous cities home to breathtaking Renaissance and Medieval architecture, mouth-watering cuisine, and fine wines accompanied by a timeless landscape of olive groves, vineyards, forests and hilltop villages. 

Choose from our biking holidays in Tuscany, where we transfer your luggage between overnight stays in friendly local B&B's and hotels, and offer high quality bike hire provided by local experts. Why not also speak to your Macs Adventure specialist about hiring an e-bike - a confidence-boosting way to explore the rolling Tuscan countryside?

Discover the wine-producing regions of Chianti and Montepulciano and stay in the city of Siena, renowned for it's 400-year-old Palio Horse Race that takes place in the Piazza del Campo and array of 13-15th century art and architecture on our leisure cycling trip Tuscany: Chianti & Siena. For road cyclists seeking an extra element of challenge, combined with authentic Italian hospitality, outstanding cultural highlights and Tuscany's classic cypress-lined winding roads then our Tour of Tuscany: Florence to Montepulciano and Florence to Siena Short Break trips are a must.