Itinerary
- Day 1
Florence
- Meals
- Breakfast
- Accommodation
- Hotel (C-Hotels)
Optional Activities
- Stroll through Florence
- Explore art history sites
Landmarks Ponte Vecchio 
- Day 2
Florence to Passignano sul Trasimeno
- Meals
- Breakfast
- Accommodation
- Hotel (Hotel Lido)
Included Activities
- Train journey from Florence to Arezzo with bike
- Stroll through Arezzo old town
- Cycling tour through Val di Chiana valley to Lake Trasimeno and Passignano sul Trasimeno (approximately 60 km)
Landmarks Arezzo Old Town Cortona Lake Trasimeno Passignano sul Trasimeno - Day 3
Passignano sul Trasimeno to Montepulciano
- Meals
- Breakfast
- Accommodation
- Hotel (Hotel Palazzo Mosela)
Included Activities
- Cycling tour along Lake Trasimeno lakeshore to Castiglione
- Cycling through Val di Chiana valley to Montepulciano (approximately 50 km)
- Cycling through Vino Nobile di Montepulciano vineyards
Optional Activities
- Explore medieval streets of Montepulciano
Landmarks Castiglione Montepulciano 
- Day 4
Montepulciano to Montalcino
- Meals
- Breakfast
- Accommodation
- Hotel (Drogheria & Locanda Franci)
Included Activities
- Cycling tour through cypress-lined roads to Montechiello
- Cycling along Strade Bianche white gravel roads
- Cycling through Val d'Orcia to Montalcino (approximately 50 km)
Optional Activities
- Visit Renaissance town of Pienza
- Taste Brunello wine in local wine bars in Montalcino
Landmarks Montechiello Pienza Val d'Orcia Montalcino - Day 5
Montalcino to Siena
- Meals
- Breakfast
- Accommodation
- Hotel (Hotel Villa Ermellina Siena)
Included Activities
- Cycling tour through Eroica routes and golden wheat fields to Siena (approximately 55 km)
- Cycling through Piazza del Campo in Siena
Landmarks Palazzo Pubblico Piazza del Campo 
- Day 6
Siena to Radda in Chianti
- Meals
- Breakfast
- Accommodation
- Hotel (Relais & Spa Vignale)
Included Activities
- Cycling tour through vineyards with mountain road views
- Cycling through white gravel roads to Radda in Chianti (approximately 30-70 km)
Optional Activities
- Stop in Vagliali for Italian cappuccino
- Enjoy classic pasta lunch in Radda
- Explore Castellina and heart of Chianti region
Landmarks Vagliali Radda in Chianti Castellina Chianti - Day 7
Radda in Chianti to Florence
- Meals
- Breakfast
- Accommodation
- Hotel (C-Hotels)
Included Activities
- Cycling tour through Chianti vineyards, olive groves and medieval villages to Florence (approximately 55 km)
- Cycling descent to Ponte Vecchio
Optional Activities
- Visit Greve in Chianti
- Enjoy Tuscan wine tasting in Florence
Landmarks Greve in Chianti Ponte Vecchio - Day 8
Florence
Optional Activities
- Extend trip or combine with Venice-Florence tour
- Extend trip or combine with Florence-Rome tour
