2026 tuscany villa vacation

Itinerary

Day 1: Welcome to Tuscany
We will meet you at 12 noon at the Florence Airport and transfer you to our villa hotel in the Tuscan countryside near Castellina-in-Chianti. Following check-in for the next five nights, assemble your bike with the assistance of our professional mechanics or fine tune your rental bike before enjoying a short spin to loosen up. This evening, we’ll enjoy our “Welcome Meeting and Dinner” at the villa.
Ride Preview: 30 minutes easy

Day 2: Colle di Val d’Elsa and Monteriggioni
Following a hearty breakfast overlooking the Tuscan countryside, begin your day with a descent to Colle di Val d’Elsa before continuing to the walled medieval city of Monteriggioni. The town along with its numerous watchtowers was built by the Sienese between 1213 and 1219 for defensive purposes: its strategic location atop a hill overlooking the Cassia Road allowed the village to control the cities of the Val d’Elsa and be on the lookout for any armies approaching Siena. This afternoon following the return to the villa, relax in the pool overlooking the Chianti countryside or choose a relaxing massage. This evening, we’ll visit nearby Castellina-in-Chianti to explore the local trattorias for dinner.
Ride Preview: 53 km; 688 meters of climbing

Day 3: Radda in Chianti and Volpaia / Siena Visit
Today’s ride is a Tuscan treasure as we cycle to some of the most beautiful and authentic villages in the Chianti region, Radda in Chianti and charming Volpaia. With views that stretch on forever across the timeless hills, the tiny village of Volpaia is the perfect spot to enjoy a coffee or two. It is also home to the Castello di Volpaia wines that are made on-site in a remarkable setting underneath the village’s medieval churches. Later this afternoon, we’ll transfer to magical Siena for a walking tour and a relaxing dinner near the Piazza del Campo!
Ride Preview: 43 km; 819 meters of climbing

Day 4: The Chiantigiana
Enjoy breakfast and a cappuccino before heading out for a full day’s ride discovering the rolling hills and charming villages of the Chianti region such as Tavarnelle Val di Pesa, Greve-in-Chianti, Panzano, and others. It will be a day of climbing and descending with views on the “Chiantigiana” that will have you stopping to take plenty of photos. This evening, we’ll enjoy a delicious Tuscan dinner at the villa to refuel for tomorrow.
Ride Preview: 60 km; 870 meters of climbing

Day 5: Crete Senesi.
Today is like Disneyland on the bike! Following breakfast, we’ll transfer into the Crete Senesi and the hilltop town of Montalcino with its views that stretch on forever! Enjoy a coffee in town before getting to ride the rolling hills of the Crete Senesi with its hilltop villas and cypress-lined roads that are straight out of a postcard. This evening, we’ll conclude your trip to Tuscany with a festive “Farewell Dinner!”
Ride Preview: 82 km; 1037 meters of climbing

Day 6: Transfer Day.
After a leisurely breakfast, it’s time to leave our Tuscan villa and transfer you to the Florence Airport. Our estimated time of arrival is 12 noon. If you need to arrive sooner, please let us know and we can arrange a private taxi at your expense. Thanks!