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Self-Guided Eroica Dirt Roads Bike Tour

Self-Guided Eroica Dirt Roads Bike Tour
Tuscany's white gravel roads, called the strade bianche, wind 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.

Day 1 Gaiole  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 sheep's cheese (called pecorino), 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.

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 7-8 Radda  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.

Note:  There are no busses from Radda on Sundays. If you schedule your tour to end on a Sunday you will have to pay for a taxi. Email us for taxi rates.

Reserve This Tour Detailed Itinerary

US$ 1,700 per person
(Single Supplement)

Traveling alone?
Join a self-guided tour that has already been scheduled. We can't run self-guided trips for one person, but we may have already booked a self-guided tour that works for you. More info

Group of three?
Tour prices are based on double room occupancy. Groups of three on self-guided trips have two options:
Option 1: Request a triple room. With a triple there is no single supplement. Option 2: Pay a single supplement (US$ 50/night) for the single room.

(Eroica Blackout Dates)

This tour is unavailable the first weekend of October (Friday, Saturday and Sunday). During that weekend thousands converge on Gaiole for the one-day cycling event called the Eroica. Hotels in the area are already full.

Save US$ 400 per person
Use our bike bags (panniers) instead of the luggage transfer
more info


Any date from March 1 to October 31
8 Days, 7 Nights
Route Rating
Challenging: 60% of this tour is on dirt roads. 15-30 miles (25-50 km) per day cycling over hilly terrain.

Meet / Finish
Florence / Radda in Chianti
  • 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

What's Included
  • All lodging (3 and 4 star hotels)
  • All breakfasts
  • Lunch on Day 1
  • Winery visit and wine tasting
  • Luggage transfer from hotel to hotel
  • Private van transfer from Florence on day one
  • 6 beautiful rides. Extra miles available.
  • Use of a mountain bike

Cancellations: Terms and Conditions

Tour Summary
Map and Distances

Wineries and Castles
Mountain Bikes Only
This tour has 88 miles (142 km) of dirt roads with some steep uphills and downhills. For safety reasons we provide only mountain bikes for this trip.
What if it rains?

On self-guided bike tours there is no van support. However, we do move your luggage from hotel to hotel. In the event of rain you can catch a ride with us when we move your bags, just call and make arrangements for a lift.

Why a Self-Guided Bike Tour?
Explore Tuscany at your own pace. We provide detailed route notes, luggage transfers, great accommodations, restaurant suggestions, and sightseeing notes. You choose the dates. We take care of the details.