Day 1: Florence to Greve in Chianti (35km)
Meet your guide and group in Florence. Bike fitting. Cycle south out of the city through the Florentine hills into Chianti — the transition from urban to vineyard is swift and magical. Olive groves, terracotta farmhouses, and the first vine-covered slopes appear. Arrive in Greve in Chianti, the unofficial Chianti capital — its triangular piazza surrounded by arcades. First wine tasting at a family estate. Welcome dinner in Greve. Overnight Greve area.
Day 2: Greve to Radda — Chianti Classico Heartland (40km)
The quintessential Chianti ride. Undulating roads wind through the very heart of the Chianti Classico zone: Panzano, with its famous butcher Dario Cecchini, then Castellina in Chianti with its medieval fortress. Ride the ‘Chiantigiana’ (SR222) — one of Italy’s most scenic roads, flanked by vineyards, olive groves, and cypress trees. Afternoon arrival in Radda in Chianti, a perfectly preserved medieval village with sweeping valley views. Wine tasting at an organic estate producing Chianti Classico and IGT wines. Overnight Radda.
Day 3: Radda to San Gimignano — Towers & Vernaccia (50km)
A longer, rewarding day through classic Tuscan terrain. Pass through Monteriggioni — the ‘crown of towers’ on a hill, its 13th-century walls perfectly intact, exactly as Dante described them. Continue past rolling wheat fields and sunflowers to San Gimignano, its 14 medieval towers dominating the skyline. Afternoon: explore the city of beautiful towers, taste Vernaccia di San Gimignano (Tuscany’s famed white), and visit the gelato world champion for a well-earned scoop. Overnight San Gimignano area.
Day 4: San Gimignano to Siena — Gothic Splendor (45km)
Ride through the rolling countryside south toward Siena. The terrain is gentler today, the roads quieter. Arrive in Siena, the magnificent Gothic city. Afternoon walking tour: Piazza del Campo — the great shell-shaped square where the Palio horse race has been run since the Middle Ages. Visit the Duomo with its black and white marble, Piccolomini Library, and the Baptistery. Free evening to explore Siena’s contrade neighborhoods, each with its own flag, fountain, and fierce identity. Dinner in the Campo. Overnight Siena.
Day 5: Siena to Pienza — Crete Senesi & Val d’Orcia (55km)
The most dramatic ride of the tour. Leave Siena through the Porta Romana into the Crete Senesi — a surreal landscape of eroded clay hills, lunar-like in their pale gray undulations, dotted with solitary cypresses. This is the Tuscany of Renaissance paintings. Continue into the UNESCO Val d’Orcia — the perfect Renaissance landscape where every view is a postcard. Arrive in Pienza, the ‘ideal Renaissance city’ designed by Pope Pius II. Taste pecorino di Pienza — this tiny town produces some of Italy’s finest sheep’s milk cheese. Celebration dinner. Overnight Pienza area.
Day 6: Pienza to Montalcino — Brunello & Farewell (30km)
Final ride through the Val d’Orcia to Montalcino. Gentle climbs lead to the hilltop fortress town. The reward: Brunello di Montalcino tasting at a historic estate — the perfect conclusion to a week of pedaling through Italy’s greatest wine region. Transfer back to Florence. Arrivederci!
