Itinerary
- Day 1
Cortona
Optional Activities
- Visit the Etruscan Museum
- Visit the Diocesan Museum with Fra Angelico paintings
- Explore medieval streets of Cortona
Landmarks Etruscan Museum Diocesan Museum - Day 2
Cortona
- Meals
- Breakfast
Included Activities
- Cycling round trip to Lake Trasimeno and surrounding hills
Optional Activities
- Boat trip on Lake Trasimeno to Isola Maggiore
- Visit Castiglione del Lago (alternative easier route option)
Landmarks Lake Trasimeno Isola Maggiore Castiglione del Lago - Day 3
Montepulciano - Pienza
- Meals
- Breakfast
Included Activities
- Cycling to Montepulciano and Pienza
Optional Activities
- Visit wine cellars in Montepulciano
- Explore medieval streets of Montepulciano
- Explore Renaissance architecture of Pienza
Landmarks Montepulciano Pienza 
- Day 4
Pienza
- Meals
- Breakfast
Included Activities
- Cycling tour through Orcia Valley
Optional Activities
- Visit medieval village of Monticchiello
- Sample local wines and cheeses in Pienza
- Taste Pecorino cheese aged under ash
Landmarks Orcia Valley Monticchiello 
- Day 5
Montalcino
- Meals
- Breakfast
Included Activities
- Cycling to Montalcino through Asso River valley
Optional Activities
- Mid-morning cappuccino stop in Trequanda
- Explore Etruscan village and wine town of Montalcino
Landmarks Trequanda Montalcino Asso River - Day 6
Montalcino
- Meals
- Breakfast
Included Activities
- Cycling round trip visiting Abbey of Sant'Antimo and surrounding valley
Optional Activities
- Visit Abbey of Sant'Antimo
- Climb to Castiglione d'Orcia
- Visit Bagno Vignoni
- Explore San Quirico d'Orcia
Landmarks Abbey of Sant'Antimo Castiglione d'Orcia Bagno Vignoni San Quirico d'Orcia - Day 7
Montalcino - Siena
- Meals
- Breakfast
Included Activities
- Cycling from Montalcino to Siena
Optional Activities
- Visit Monte Oliveto Maggiore monastery
- Explore medieval city of Siena
Landmarks Monte Oliveto Maggiore Crete Senesi Siena - Day 8
Siena
- Meals
- Breakfast
Optional Activities
- Extend stay in Siena for additional sightseeing
- Travel by train to Florence
- Travel by train to Rome
Landmarks Siena
