Morning: Arrive in Florence, check into your hotel and collect your road‑bike from the local shop. Enjoy a light breakfast at a café overlooking the Piazza del Duomo while adjusting your gear.
Afternoon: Pedal along the Arno River to the historic Uffizi Gallery and then ride up to the Boboli Gardens for sweeping city views. Take a short break at a trattoria for a traditional Tuscan lunch.
Evening: Cruise through the illuminated streets to the Ponte Vecchio, then dine on Florentine steak at a riverside restaurant. Return the bike to the shop for a quick maintenance check.
Find HotelsMorning: Leave Florence on the famed Via Francigena cycling route, heading into the rolling hills of Chianti. First stop is the charming town of Greve in Chianti, where you can sip a glass of Chianti Classico.
Afternoon: Continue to Castellina in Chianti, exploring its medieval walls and visiting a local winery for a tasting and light lunch. The gentle climbs provide stunning vineyard panoramas.
Evening: Arrive in the historic village of Radda in Chianti, where you’ll enjoy a relaxed dinner of ribollita soup and Tuscan bread. Overnight at a family‑run agriturismo.
Find HotelsMorning: Depart Radda and cycle the scenic route to Siena, arriving at the iconic Piazza del Campo. Take a guided walking tour to learn about the Palio horse race and the city’s Gothic architecture.
Afternoon: Ride up to the Duomo di Siena for its breathtaking marble façade and interior frescoes. Enjoy a leisurely lunch at a trattoria serving pici pasta with wild boar ragù.
Evening: Explore the quiet streets of the Contrada neighborhoods, then dine on Tuscan cheese and honey while watching the sunset from the city walls. Return your bike to the Siena rental shop for a quick service.
Find HotelsMorning: Begin the ride toward the UNESCO‑listed Val d'Orcia, passing through golden wheat fields to the medieval town of Pienza. Sample fresh pecorino cheese at a local farm.
Afternoon: Continue to Montepulciano, climbing to its historic fortress for panoramic views of the countryside. After a light lunch of bruschetta and local wine, start the gentle descent back toward Florence.
Evening: Arrive in Florence for a final celebratory dinner in the Oltrarno district, reflecting on the journey’s highlights. Return the bike, pack, and prepare for departure the next day.
Find HotelsIf you have extra days, consider extending the loop to include the coastal town of Livorno or the medieval hilltop city of San Gimignano for more cycling variety. To shorten the trip, you can combine Day 2 and Day 3 by cycling directly from Chianti to Siena, skipping the Val d'Orcia segment, which reduces travel time while still experiencing Tuscany’s iconic landscapes.