Itinerary
- Day 1
Florence
You'll arrive in Florence and spend time walking around the city. There's plenty of art and history to take in as you wander through the streets and get a feel for the place.
Optional Activities
- Stroll through Florence
- View world-class art and historical sites
Landmarks Florence 
- Day 2
Florence to Passignano
Early morning train takes you to Arezzo where you'll walk through the old town. From there you start cycling about 60km through Val di Chiana valley. The route passes by Cortona and goes through olive groves before reaching Lake Trasimeno. You'll finish the day in Passignano, a historic spot right on the water.
- Meals
- Breakfast
Included Activities
- Train journey Florence to Arezzo with bike included
- Walk through Arezzo old town
- Cycle through Val di Chiana valley
- Cycle through olive groves and hills to Lake Trasimeno
- Cycle along lake shore to Passignano
Landmarks Arezzo Val di Chiana Cortona Lake Trasimeno Passignano - Day 3
Passignano to Montepulciano
Today's 50km ride follows the lakeshore to ancient Castiglione with nice views across Lake Trasimeno. After that you'll leave Umbria and head into Tuscany where the landscape gets hillier. The cycling takes you through vineyards growing Vino Nobile de Montepulciano before you reach the town perched on the mountain. Later in the evening you can explore the medieval alleyways.
- Meals
- Breakfast
Included Activities
- Cycle along Lake Trasimeno lakeshore to Castiglione
- Cycle through Vino Nobile de Montepulciano vineyards
- Explore Montepulciano medieval alleyways
Landmarks Castiglione del Lago Montepulciano - Day 4
Montepulciano to Montalcino
Starting with winding roads lined with cypress trees, you'll reach the fortified village of Montechiello. From there the route heads along white Strade Bianche roads to Pienza, a Renaissance town known from the Gladiator film. You'll then cycle through Val d'Orcia to Montalcino where you can stop at wine shops and try Brunello, the region's famous wine. This 50km day covers some beautiful rolling terrain.
- Meals
- Breakfast
Included Activities
- Cycle to Montechiello fortified village
- Cycle Strade Bianche white roads to Pienza
- Cycle through Val d'Orcia landscape
- Visit Montalcino wine shops and sample Brunello wine
Landmarks Montechiello Pienza Val d'Orcia Montalcino - Day 5
Montalcino to Siena
You'll cycle about 55km following the famous Eroica routes through golden wheat fields and hilly landscape. Cypress avenues and stately homes line parts of the route as you head toward Siena. The final stretch takes you across the Campo square, the spot where the annual Palio horse race happens. The views of Palazzo del Publicco are nice from this vantage point.
- Meals
- Breakfast
Included Activities
- Cycle Eroica routes through wheat fields
- Cycle past cypress avenues and stately homes
- Cycle to Siena and across Campo square
Landmarks Palazzo del Pubblico Piazza del Campo - Day 6
Siena to Radda
This shorter 30km ride starts with views over vineyards on a mountain road. You'll take a break in the stone village of Vagliali to grab an Italian cappuccino. Then it's more cycling on white roads through vineyards and forests to reach Radda. Lunch here features typical pasta, giving you energy for the route. There's an optional tour through Castellina in the heart of Chianti if you want to add 40km to your day.
- Meals
- Breakfast
Included Activities
- Cycle over mountain roads with vineyard views
- Cycle through white roads and vineyards to Radda
- Explore Radda village
Optional Activities
- Break at Vagliali stone village for Italian cappuccino
- Typical pasta plate lunch
- Optional tour via Castellina through Chianti (+40km)
Landmarks Vagliali Radda in Chianti Castellina in Chianti - Day 7
Radda to Florence
The hilly route continues toward Florence over about 55km. You'll pass through vineyards, olive groves and medieval villages, including Greve in Chianti. Typical stone houses and cypress avenues dot the landscape with good views throughout. After a long descent you'll reach Ponte Vecchio and finish your Tuscan cycling week in Florence.
- Meals
- Breakfast
Included Activities
- Cycle through vineyards and olive groves to Greve in Chianti
- Cycle through medieval villages
- Long descent to Ponte Vecchio in Florence
Landmarks Greve in Chianti Ponte Vecchio - Day 8
Florence
Today you'll depart individually from Florence, heading home after your week cycling through Tuscany.
- Meals
- Breakfast
