Strade Bianche Bike Tour

Your guides will meet you at the Chiusi train station for a transfer to our villa in the Tuscan countryside, a stylishly renovated farmhouse and our home for the rest of the week. Enjoy a light lunch on the terrace before getting fitted to your bike. We won’t waste any time hitting the famous white roads of Tuscany—the strade bianche—beginning right out the door of our villa. It feels like a return to the 13th century as we course along these ancient paths, passing through Petroio’s cobbled streets and greeting locals as they tend their olive groves. Explore routes known only to resident cyclists before returning to the villa, where refreshment takes the form of a cold drink or a dip in the pool. Tonight we dine at our favorite truffle restaurant and learn the true meaning of buon appetito.

Meals: Lunch / Dinner
Destinations: Petroio, Montisi
Accomplished: 31 miles / 50 km, elevation gain: 3,250 feet / 991 meters (21 km of which are on gravel roads)
Accommodations: Podere Ferranesi

L’Eroica—meaning “The Heroic”—is a celebration of the golden age of cycling. The event takes place every October when thousands of hardened cyclists travel back in time to ride these gravel roads on primitive machines of the past. The heavy lugged-steel bikes with down-tube shifters and impossible gear ratios are no match for the red wine in the participant’s water bottles and the hardman (and hardwoman) mentality. Today, we’ll have our own taste of cycling’s heroic origins as we join one of the toughest gravel sections of L’Eroica: a 16-kilometer climb where the maximum gradient is a challenging 12 percent. Ride through the heart of Brunello di Montalcino, Tuscany’s most celebrated wine region, and stop for lunch at a winery owned by a passionate local cyclist. We’ll continue on through the town of Montalcino before following the gravel roads back to our villa. Tonight the villa’s chef will prepare a delectable meal.

Meals: Breakfast / Lunch / Dinner
Destinations: Buonconvento, Castelnuovo, Montalcino
Accomplished: 63 miles / 102 km, elevation gain: 6,639 feet / 2,024 meters (47 km of which are on gravel roads)
Accommodations: Podere Ferranesi

Spring brings red poppy blossoms to the vibrant green wheat fields of Tuscany, and nowhere is the bloom more brilliant than the hills of the Val d’Orcia, a UNESCO World Heritage Site. As we pedal through these corridors of proud cypress trees, the scenery may look familiar from such films as Gladiator and The English Patient. Follow the gravel tracks off the beaten path through a timeless slice of Tuscany and enjoy an espresso in Monticchiello, overlooking the roads we just conquered. Lunch is waiting for us back at our villa. Tonight, hit the town of Montefollonico, a hidden gastronomical hub and home to our favorite little restaurant—but first, stop at our friend Vittorio’s 13th-century home and wine cellar for a tasting.

Meals:  Breakfast / Lunch / Dinner
Destinations: Monticchiello, Pienza
Accomplished: 67 miles / 108 km, elevation gain: 7,262 feet / 2,214 meters (59 km of which are on gravel roads)
Accommodations: Podere Ferranesi

After an early stretch and breakfast, head out into magical Chianti. We’ll traverse the Crete Senesi region on a 10-kilometer gravel climb, making our way through wheat fields before we hit the vineyards of this celebrated wine region. Counting castles and old hilltop hamlets, we’ll work up our appetite for lunch at our friend Serena’s house. In true Italian fashion, she’s spent days in front of the stove in anticipation of our arrival. This afternoon, witness the speed and fury of the Strade Bianche race, in which professionals like Peter Sagan and Greg Van Avermaet battle over the same gravel roads we’ve been riding. We’ll practically touch the action as it speeds past Serena’s house—don’t be rattled if the pros take one of the steepest gravel sections a bit faster than we did. After the race breezes by, pedal back to our villa or take a luxurious lift in the van. Tonight’s dinner at the villa will fuel us for the challenge that awaits us tomorrow.

Meals:  Breakfast / Lunch / Dinner
Destinations: Asciano, Castelnuovo Berardenga
Accomplished: 42 miles / 69 km, elevation gain: 3,795 feet / 1,157 meters (24 km of which are on gravel roads)
Longer Option: 68 miles / 110 km, elevation gain: 6,347 feet / 1,935 meters
Accommodations: Podere Ferranesi

Now that we’ve feasted on fine food and wine, tested our legs on some of the region’s precipitous climbs, and refined our technical skills on gravel roads, it all culminates in the Gran Fondo Strade Bianche. The annual big ride includes some of the most challenging sections of gravel in Bella Toscana! Depart early this morning for the medieval walled city of Siena where this legendary route begins and ends hours later, after the brutal climb up Via Santa Caterina and the finish in Piazza del Campo. After the race, we’ll regroup in the city center and have lunch before returning to our villa. Tonight, reflect on a fabulous week of riding as we enjoy a final sunset over the Tuscan hills and indulge in a celebratory meal prepared at the villa.

Meals: Breakfast / Lunch / Dinner
Destinations: Siena
Accomplished: 86 miles / 139 km, elevation gain: 6,668 feet / 2,033 meters (31 km of which are on gravel roads)
Accommodations: Podere Ferranesi

Our last morning in Tuscany presents plenty of options: sleep in, savor a slow breakfast, or take a final ride through the hills around our villa. Your guides will return you to the Chiusi train station, bidding you farewell before you depart for your next destination. 

Meals: Breakfast
Destinations: San Giovanni d’Asso, Chiusi
Accomplished: Optional morning ride