Relaxed Tuscany Bicycle Tour 4 Night

Your Tuscan adventure begins in Florence, the Renaissance capital, where you’ll meet your guide in the morning. After a proper bike fitting, your guide will accompany you out of the city, navigating the lively streets and leading you into the heart of Chianti’s picturesque landscapes. Once outside Florence, the ride becomes a tranquil journey through vineyards and olive groves, leading to Greve in Chianti, the gateway to Chianti Classico wine country. Upon arrival, check into your charming hotel, relax, and explore the historic town square, artisan shops, and local enotecas. Your luggage will be waiting for you at the hotel, so feel free to unwind with a glass of Chianti wine before enjoying an included traditional Tuscan dinner.

Today’s ride takes you deeper into Chianti’s wine country, following scenic country roads lined with cypress trees and vineyards. Along the way, stop in Castellina in Chianti, a delightful medieval town filled with wine cellars, charming cafés, and historic stone streets. For those who want a longer ride, an optional 20km extension is available, offering extra time in the saddle while soaking in stunning panoramic views. Arriving in Radda in Chianti, check into your elegant countryside hotel, then take a leisurely stroll through this charming hilltop village. Tonight, enjoy another included dinner featuring the best of Tuscan cuisine.

Today is all about exploring the best of Chianti on a scenic loop ride through the region’s most picturesque spots. Visit Badia a Coltibuono, a stunning former abbey-turned-winery, and pedal through Gaiole in Chianti, a charming town known for its wine festivals and medieval architecture. For those who want a little extra adventure, an extended ride will take you to Castello di Meleto, a historic Tuscan castle with breathtaking views and an optional wine tasting experience. After a day of cycling and sightseeing, return to Radda and enjoy an evening at your own pace. Tonight’s dinner is on your own—take the opportunity to discover a local trattoria or enoteca, where you can indulge in fresh handmade pasta, wild boar ragu, or a perfectly grilled bistecca alla Fiorentina.

Your final ride is a breathtaking 33km journey along quiet, rolling backroads leading to Siena, one of Tuscany’s most iconic and beautiful medieval cities. Along the way, soak in the expansive views of vineyards, hilltop villages, and golden wheat fields, a postcard-perfect Tuscan landscape. Upon arrival in Siena, check into your hotel located inside the historic town gates, placing you right in the heart of the action. Spend the afternoon exploring the stunning Piazza del Campo, visiting the magnificent Siena Cathedral, and getting lost in the city’s winding medieval streets. Tonight, dinner is on your own, giving you the chance to experience Siena’s renowned culinary scene. Find a cozy restaurant serving pici pasta with truffle sauce, wild boar stew, or a glass of Brunello di Montalcino while taking in the city’s magical evening ambiance.

After a leisurely breakfast, it’s time to say goodbye to Tuscany’s rolling hills and charming villages. We’ll help coordinate your train transfer back to Florence or your next destination. Whether you’re continuing your Italian adventure or heading home, you’ll leave with incredible memories of cycling through Tuscany’s most breathtaking landscapes.