Strade Bianche Bike Tour

Your guides will meet you at the Chiusi train station for a transfer to our first hotel in the Tuscan hilltop hamlet of San Quirico D’Orcia. Enjoy a light lunch in town before getting fitted to your bike. We won’t waste any time hitting the famous white roads of Tuscany—the strade bianche—starting just three miles into our first ride. It feels like a return to the 13th century as we course along ancient paths, passing through the Orcia Valley and Pienza. Here, do as the Italians do and stop for a coffee in the town’s oldest bar, then return to our hotel on routes known only to local cyclists. Tonight we dine at our hotel and learn the true meaning of buon appetito.

Meals: Lunch / Dinner
Destinations: San Quirico D’Orcia, Pienza
Accomplished: 26 miles / 42 km (16 km of which are on gravel roads), elevation gain: 2,253 feet / 687 meters
Accommodations: Palazzo del Capitano and Villa del Capitano

L’Eroica—meaning “The Heroic”—is an event that celebrates the golden age of cycling. It 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 participants’ water bottles and the hardman (and hardwoman) mentality. Today, we’ll get our own taste of cycling’s heroic origins as we join one of the toughest gravel sections of L’Eroica Montalcino: a 14-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 and former pro cyclist whose business honors the region’s rich cycling history. We’ll continue through the town of Castiglione d’Orcia before returning to our hotel, where our soigneurs are waiting to reward us with well-deserved massages. Tonight, we’re invited to a very special farm-to-table dinner, prepared with ingredients that are crafted completely by local hands.

Meals: Breakfast / Lunch / Dinner
Destinations: Buonconvento, Castiglion del Bosco, Castiglione d’Orcia
Accomplished: 56 miles / 90 km (33 km of which are on gravel roads), elevation gain: 6,400 feet / 1,951 meters
Accommodations: Palazzo del Capitano and Villa del Capitano

All the professional teams have arrived in Siena, ready to test their legs on tomorrow’s race course. We will do the same, previewing the final 54 kilometers of the men’s pro course which also appears on Sunday’s Gran Fondo route. Team cars and pro riders will cross paths with our peloton as we pass through the mythical Monte Sante Marie gravel section dedicated to Fabian Cancellara—the only rider to win the race three times. We arrive in Siena via the infamous Santa Caterina climb, emerging into the iconic Piazza del Campo where lunch is waiting. In the afternoon, our pro soigneurs will prepare our legs for the big cycling weekend ahead. Tonight, explore Siena on your own for dinner—your guides can share their favorite trattorias or where to find the best truffle dishes in town.

Meals: Breakfast / Lunch
Destinations: Asciano, Castelnuovo Berardenga, Siena
Accomplished: 55 miles / 88 km (28 km of which are on gravel roads), elevation gain: 5,206 feet / 1,587 meters
Accommodations: Grand Hotel Continental Siena

The excitement of race day is in the air! Wake up at the center of the cycling world and walk to see the women’s race depart, then mingle at the buzzing team buses before we take a spin of our own. It’s a short ride to lunch at our friend Serena’s house and in true Italian fashion, she’s spent days at the stove in anticipation of our arrival. This afternoon, witness firsthand the speed and fury of the Strade Bianche race, in which professionals like Tadej Pogačar, Wout van Aert, and Julian Alaphilippe 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, take a lift in the van to our hotel in the heart of Siena. Tonight’s dinner at the best pizzeria in town will fuel us for the challenge that awaits us tomorrow.

Meals:  Breakfast / Lunch / Dinner
Destinations: Pieveasciata, Pianella
Accomplished: 24 miles / 39 km, elevation gain: 2,007 feet / 612 meters
Accommodations: Grand Hotel Continental Siena

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! Wake up in the medieval walled city of Siena—our hotel is mere meters from where the 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 recovering at the hotel with another treatment from our soigneur. Tonight, reflect on a fabulous week of riding as we indulge in a celebratory dinner at one of Siena’s best restaurants.

Meals: Breakfast / Lunch / Dinner
Destinations: Siena
Accomplished (Medio Fondo): 54 miles / 87 km (22 km of which are on gravel roads), elevation gain: 4,176 feet / 1,273 meters (545 meters on gravel)
Longer Option (Gran Fondo): 86 miles / 139 km (55 km of which are on gravel roads), elevation gain: 6,668 feet / 2,033 meters (1,285 meters on gravel)
Accommodations: Grand Hotel Continental Siena

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

Meals: Breakfast
Destinations: Siena, Chiusi