Ride the famous ‘strade bianche’ white gravel roads of Tuscany, explore the medieval towns and enjoy world-famous Tuscan food and wine on this dream trip in September 2022.
Highlights:
- The famous gravel roads of the ‘L’Eroica’ and ‘Strade Bianche’ races
- The gorgeous Val d’Orcia UNESCO World Heritage area
- The historic towns and villages, including stays in Pienza and Castellina in Chianti
- Rest day in Siena with its countless monuments to take you back in time
- The wine regions of Chianti, Brunello and Vino Nobile
Below is a summary of our itinerary. Full details including altitude profiles are in our brochure.
Friday September 2nd: Overnight flight to Rome, Italy.
Saturday September 3rd: Arrival in Rome, group transfer to Pienza (3 hrs) We’ll be there to greet you at Rome airport. Our private bus will take you to our hotel in Pienza where we’ll be staying for the first two nights. Assembly of bikes or pick-up of rental bike. We’ll have time to explore the historic town center in the afternoon.
Sunday September 4th: Val d’Orcia (distance: 51 mi, vertical: 5,000 ft, 17 miles gravel) After only three miles we’ll hit the first gravel stretch on our first ride. Mid morning we can stop for a quick cappuccino in Montepulciano, one of the most famous Tuscan hill top towns. We continue our ride through Val d’Orcia, a place of exceptional beauty and UNESCO World Heritage site. We’ll loop back to Pienza via some of the shooting locations of the movie ‘Gladiator’.
Monday September 5th: Pienza to Siena (55 mi, 5,000 ft, 28 miles gravel) A tough stage that includes long gravel stretches of the famous L’Eroica and Strade Bianche races. We’ll be mostly in remote rural areas where we can enjoy the Tuscan countryside at its best. The pool at our hotel on the outskirts of Siena will be well appreciated after this epic day!
Tuesday September 6th: L’Eroica Chianti Section (50 mi, 4,800 ft, 16 miles gravel) More classic gravel roads today when we ride the section of L’Eroica through the hills of the Chianti region. We’ll pass by famous vineyards around the towns of Radda and Gaiole. The last gravel stretch of the day is at the Castello di Brolio castle with spectacular views.
Wednesday September 7th: Rest Day Time to recover! We have arranged for a guided walk in Siena in the morning. You can spend the rest of the day at the hotel’s pool or enjoy this incredible medieval city.
Thursday September 8th: Siena to Vescine (53 mi, 5,400 ft, 23 miles gravel) After three nights it is time to say goobye to Siena. Hopefully the rest day has brought your climbing legs back in shape because you’ll need them today. There are some steep gravel roads on the menu! After our first gravel sector of the day, we’ll pass by the 13th century Monteriggioni castle which we can enter and explore. Shortly after we’ll ride through Colle di Val d’Elsa, a great place for a coffee stop. Later we’ll see the famous towers of San Gimignano from a distance. We can have lunch in the town of Poggibonsi before some more steep climbing on our way to hotel Borgo di Vescine, an entire medieval hamlet which has been restored and now is an upscale resort with an award-winning restaurant. It is in a peaceful setting with a great pool and its own winery.
Friday September 9th: Chianti Loop (50 mi, 6,500 ft, 9 mi gravel) Mostly paved roads today but that doesn’t mean that it will be an easy ride. The longest gravel section comes early in the ride after the climb to Volpaia, renowned for its excellent wines. After a brief coffee stop at the main square of Greve, we have a steep climb on the way to the impressive Badia di Passignano Abbey. A short but steep gravel climb is just before our lunch in Tavarnelle. Then one more steep climb and some longer easier grades on our way back to Borgo di Vescine.
Saturday September 10th: Early ride and afternoon transfer (24 mi, 2,400 ft, 5 mi gravel) We’ll go for a beautiful short ride in the morning with two more gravel stretches. The second is a rough and steep four miles uphill section. Back at the hotel we’ll shower, pack the bikes (if you brought your own) and have lunch. A private bus will take us to our hotel near Rome airport in the afternoon. We’ll have a celebratory dinner tonight to mark the end of our trip.
Sunday September 11th: Flight home The hotel shuttle will take you to the airport for your flight home.
This trip includes:
- Private group airport transfers to/from Rome airport
- Eight nights of hotels, including all breakfasts and dinners
- Fully supported rides, with guides on bikes and support vehicle
- Water, snacks and fruit on the rides
This trip is designed for gravel bikes. You can bring your own or rent one for $400 for the trip.
Price: $3,495 per person in a shared double/twin room. Single room supplement: $895
See our brochure for more details or contact us for more information.
Ready to book? Use our online sign-up form.
