Tuscany Road Biking Tour Itinerary

Day 1 Arrival in Siena

When you arrive in Siena, you’ll enjoy a welcome drink, get your bike fitted, and then have dinner with the group.
Overnight Location: Hotel in Siena
Distance: None
Meals: Dinner

Day 2 Siena and Chianti Loop Bike Ride

You first ride takes place in the Chianti Hills area. This area, famous all over the world, is the birthplace of Chianti wine. You’ll start your cycling day riding through rolling hills surrounded by vineyards.

Once you arrive in Radda in Chianti, you’ll stop for a cappuccino and cornetto in the magnificent old square. After your stop, keep on riding with views of vineyards and historic villages. At the hotel, wind down in the swimming pool and get ready for a delicious dinner.
Overnight Location: Hotel in Siena
Distance: 70km
Meals: Breakfast, dinner

Day 3 Bike to Montalcino

After breakfast, you’ll ride towards Monteroni D’Arbia on quieter secondary roads through the magnificent Val d’Arbia. You will then continue towards Asciano, with its splendid Monte Oliveto Maggiore abbey. Riding up and down between hills and cypress trees, you will arrive at Buonconvento in the Ombrone Valley.

The final stretch of the day’s ride takes you to your destination, Montalcino. This town is well-known for its production of the famous Brunello wine, which is never sold less than five years after the grape harvest.
Overnight Location: Hotel in Montalcino
Distance: 75km
Meals: Breakfast, dinner

Day 4 Montalcino Loop Bike Ride

Today is all about the unique Val D’Orcia as you ride on peaceful backroads. You’ll start your day with the descent from Montalcino to Torrenieri, then you will ride through ancient villages, where you’ll have breaks for cappuccino and espresso.

Stop to visit the splendid San Quirico d’Orcia, where you can have a lunch in a typical “trattoria” to recovery energy for taking on the demanding Montalcino ascent. An exclusive dinner in this fairytale village will end your day.
Overnight Location: Hotel in Montalcino
Distance: 68km
Meals: Breakfast, dinner

Day 5 Bike to Acquapendente

San Quirico d’Orcia is the first village you’ll encounter today, and the spa in its hamlet of Bagno Vignoni is famous. Radicofani, a wonderful village dominated by a castle, is waiting for you further along the way.

Finally, you’ll ride into the Lazio region at Acquapendente, where you will be justly rewarded for your efforts with a visit to the historical centre and an excellent dinner.
Overnight Location: Hotel in Cantiano
Distance: 72km
Meals: Breakfast, dinner

Day 6 Bike to Lake Bolsena

Ride back, briefly, into the Tuscany region and arrive in Pitigliano, with its characteristic historical center called “Little Jerusalem” because of the presence of an ancient Jewish community. After leaving Pitigliano, head for Lake Bolsena, where Civita di Bagnoregio is waiting for you. Here, a very different landscape will provide the ideal setting for an evening in good company with a delicious dinner.
Overnight Location: Hotel in Bolsena
Distance: 65km
Meals: Breakfast, dinner

Day 7 Departure

After a wonderful week, you’ll head back to Siena to depart. Safe travels!
Overnight Location: None
Distance: None
Meals: Breakfast