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Eroica Dirt Roads Bike Tour

Tuscany's white gravel roads, called the strade bianche, zig zag through the rural countryside. These unpaved roads are attracting more and more cyclists thanks in large part to a one-day cycling event called the Eroica. This self-guided bike tour follows the Eroica itinerary, meandering 143 miles (230 km) through the Tuscan countryside. Sixty percent of the tour is on dirt roads. The riding is challenging, but it is not the Alps or Pyrenees. Steep climbs lead to breathtaking vistas, while testing downhills get your adrenaline flowing. These are farmer's roads connecting farmhouses and fields. The dirt roads are virtually car free and the scenery is classic Tuscan. 


  • Explore the Brolio Castle

  • Brunello winery tour

  • Climb the walls of the Montalcino Castle

  • The Tuscan hill towns of Siena, Montalcino, Pienza, and Radda

  • Beautiful vistas of vineyards and olive groves

  • Peaceful country back roads

US$ 1,700 per person, double occupancy


Any date, Mar 1 to Dec 1

Single Supplement
+ US$ 400 for single room occupancy


8 Days, 7 Nights

Meet / Finish
Florence / Radda in Chianti

Route Rating
Challenging: 10-33 miles (15-53 km) per day over hilly terrain. Extra miles available.


Bikes and Gear >

Terms and Conditions >

Day 5:  Pienza

Cycle to Pienza, a Renaissance jewel in the middle of the Tuscan countryside. In 1459 Pope Pius II began transforming the town into Italy's first model city; an ideal Renaissance creation of palaces, churches, and piazzas. Today Pienza is a perfectly preserved idyllic hill town. 

Day 6:  Asciano

Gently winding farm roads take you to Asciano, a typical medieval borough surrounded by 14th Century walls. The town's main pedestrian thoroughfare is lined with small shops selling local olive oil, wine, and cheese.

Day 7 and 8:  Radda in Chianti

Chianti vineyards line the road to Radda, a beautiful medieval town enclosed in large defensive walls. Narrow medieval streets lead to the town's main square. Your four-star hotel is located in an ancient palatial residence. Your cycling holiday ends in Radda. On day eight depart by bus or taxi. We will be happy to assist you with your post-tour travel planning. 

Day 1:  Gaiole in Chianti

We meet in Florence and shuttle to Gaiole. You have lunch in Gaiole with your tour coordinator who reviews the tour and provides route notes and maps. Warm up ride to the Badia a Coltibuono winery. 

Day 2:  Siena

On your way to Siena stop at the Ricasoli castle and winery. Tour the castle and try their award winning wines. The road to Siena takes you off the beaten path through sleepy villages and an outdoor sculpture garden. Your Siena hotel is in the historic center within easy walking distance of the main sights.

Day 3:  Buonconvento

A winding dirt road lead you through a changing landscape called the Le Crete. Bright green wheat fields in spring make way for brilliant yellow sunflowers in summer. This particularly scenic area of Tuscany is known for pecorino cheese, artichokes, and white truffle mushrooms.

Day 4:  Montalcino

Ride to Montalcino, a fairytale hilltop town immersed in the breathtaking Val d'Orcia National Park. Climb the ramparts of the Montalcino castle for spectacular 360-degree views. Italy's best red wine, called Brunello, is produced here. An optional winery tour is available. 

Daily Itinerary

Daily Itinerary

Daily Distance

Daily Distance


Castello di Spaltenna
Gaiole in Chianti (1 night)

The Castello di Spaltenna is an ancient "castle" turned luxury hotel. The hotel has a Michelin-rated restaurant serving traditional Tuscan fare.

hotel website >

Hotel Athena
Siena (1 night)

A modern four-star hotel with all of the comforts. The Athena is located in the historic center and offers a beautiful terrace with views of Siena.

hotel website >

Hotel Ghibellino
Buonconvento (1 night)

The Ghibellino is a small modern hotel located on the edge of the historic center of Buonconvento. Rooms are modern, quiet, and air-conditioned.

hotel website >

Hotel Dei Capitani
Montalcino (1 night)

Situated in the historical center of Montalcino, this 18th Century building has a panoramic pool. Rooms are air-conditioned and offer breathtaking views.

hotel website >


Hotel Corsignano
Pienza (1 night)

The Corsignano has breathtaking views of the Orcia Valley and offers a terrace with a hot tub. Rooms are spacious and modern.


hotel website >


Hotel La Pace Asciano (1 night)
Hotel La Pace is located just outside the historic center of Asciano. The hotel has comfortable rooms, a lovely garden, and a swimming pool.

hotel website >

Hotel San Niccolo'
Radda in Chianti (1 night)

This four-star hotel is located in a 15th Century palace. The rooms feature wooden ceiling beams, terracotta floors, and marble bathrooms.

hotel website >

What's Included

What's Included

  • All lodging (three and four star hotels)

  • All breakfasts

  • One lunch

  • Winery visit and wine tasting

  • Luggage transfer from hotel to hotel

  • Private van transfer from Florence on Day 1

  • Six beautiful rides (extra miles available)

  • Use of a high-end bicycle (hybrid, road bike or e-bike)

  • Use of a helmet

  • Souvenir water bottle to keep

Departure from Radda, End of Tour

The bike tour will end in the town of Radda in Chianti. There is no train station in Radda so you will have to take a public bus or taxi. The bus ride to Florence takes 2.5 hours. It is a 1-hour bus ride to Siena. Taxis can also be arranged. We will be happy to help you with your travel planning.

Use our Bike Bags (Panniers) and Save

Save US$ 50 per person.  Pack what you need in our bike bags (panniers) and leave the rest of your luggage with us. We will deliver your remaining luggage to the last hotel.

Siena Hotel Supplement During Palio

During the Palio (Siena's horse race) hotel prices triple. A surcharge of US$ 100 per person will apply for if you stay in Siena Jun 29-30, Jul 1-2, or Aug 13-16.

What If It Rains?

On self-guided tours there is no van support. But, we do move your luggage. If it rains you can catch a ride with us when we move your bags, just call to make arrangements.

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