Tuscany Challenge Bike Tour

  • Region: Italy
  • Destination: Tuscany
  • Duration: 7 Days / 6 Nights
  • Level: Four
  • Price From: $4595
  • Single Supplement: $550


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Explore the iconic Italian countryside as you cruise through its cypress lined byways and climb into its ancient Etruscan villages perched atop vine-covered hills on the Tuscany Pro Bike Tour. Challenge yourself on the training grounds of cycling legends; The Mont Amiata, the ridges of the Crete Senesi and the valleys surrounded by the rolling hills of Montalcino and Montepulciano. Achieve peak performance atop tour-tested Cannondale bikes and with professional road support that never leaves your side. Reenergize with local treats like fresh pici pasta, pecorino cheese, and garden fresh bruschetta with local olive oil. Top off all this spectacular riding with unforgettable visits to Vittorio Innocenti’s private cantina and the Piazza del Campo in Siena, as well as the chance to sample the finest Brunello, Super Tuscan, Vino Nobile, and Chianti Classico wines.


Tour by Day

Day One: Welcome to Tuscany!
Your guides will greet you at the train station in Chiusi and drive you up into the hills. After toasting our arrival with a welcome Prosecco, we’ll get fitted on our top-of-the-line Cannondale road bikes. Our route takes us along a rolling ridge past the hill town of Montepulciano before starting the first of many thrilling descents. This particular one follows the famous s-curves of the cypress-lined road above Montichiello before dropping into the scenic Orcia Valley. The climb back to the hotel will be the first test of our legs and will be rewarded with an intimate Tuscan evening at our favorite local restaurant, La Botte Piena.

Meals: Light Lunch / Dinner
Destinations: Montepulciano, Montichiello, Orcia Valley, Montefollonico
Accomplished: 26 miles / 42 km, elevation gain: 514 meters
Accommodations: La Chiusa

Day Two: Monte Amiata
Set off today for Tuscany’s pre-eminent climb: Monte Amiata. Cycling through the historic town of Pienza and across the Orcia Valley on a 19-kilometer approach, we’ll arrive at the base of the mountain. The next 27 kilometers up the dormant volcano are almost all uphill. Professional roadside support will be with us the whole way to ensure we have everything we need to achieve peak performance. Enjoy a well-earned, scenic lunch in the restaurant at the top before the descent and the final climb back to Montefollonico. Tonight we’ll enjoy a private tour of our friend and local winemaker Vittorio Innocenti’s cantina. Taste his traditional Vino Nobile and Vin Santo, then enjoy an exceptional dinner with our friends Dania and Umberto, the owners of La Chiusa.

Meals: Breakfast / Lunch / Dinner
Destinations: Pienza, Orcia Valley, Monte Amiata, Montefollonico
Accomplished: 70 miles / 113 km, elevation gain: 1,784 meters
Accommodations: La Chiusa

Day Three: Siena and the Crete Senesi
Today is a chance to recover from Amiata. Spin through forests and pastures on the way to the sleepy town of Trequanda before the landscape opens up as we enter the scenic countryside of the Crete Senesi. As we cycle past the area’s expansive, golden wheat fields, we will immediately understand why the area is one of the most heavily photographed routes in the world. Along the way we’ll stop for a picnic lunch before continuing onto the famous Strade Bianche. Arriving in Siena we’ll discover a gem of a medieval city with beautifully preserved Gothic architecture. Shop in the beautiful Piazza del Campo, regarded by many as the most beautiful in all of Italy, before dinner at one of our favorite local restaurants.

Meals: Breakfast / Picnic Lunch / Dinner
Destinations: Trequanda, Asciano, Arbia, Siena
Accomplished: 32 miles / 51 km, elevation gain: 569 meters climbing (Longer option: 62 miles / 99.5 km)
Accommodations: Borgo Grondaie 

Day Four: San Galgano Loop
From Siena, we will take the back route into the countryside following a quiet lane lined with stone walls, vineyards, and olive trees. Arriving in San Casciano, begin a wild descent to the valley below before a wooded climb into one of Tuscany’s largest forests. After cresting the hill, we’ll cycle to the medieval Abbey of San Galgano. The roofless main church is one of the most evocative sites in Italy. We’ll have a picnic lunch and explore the grounds before looping back to Siena. Tonight is yours to explore the town of Siena and our guides will be happy to point you to a favorite local trattoria for dinner.

Meals: Breakfast / Picnic Lunch
Destinations: San Casciano, San Galgano, Siena
Accomplished: 50 miles / 80.5 km, elevation gain: 1,020 meters climbing
Accommodations: Borgo Grondaie

Day Five: Crossing Chianti
Cycle north today into the famous Chianti hills. Passing rows of olive and cypress trees, we’ll climb a ridge ride through the gorgeous Chianti Classico estates of Bossi and San Felice. Start the day’s first big climb over the main Chianti ridgeline with grades reaching over 15%. An exhilarating descent will bring us to lunch at a great local restaurant in Montevarchi before the second big climb back into the Chianti hills. The rest of the ride follows the ridge, passing through the wine village of Radda before ending at our final lovely hotel. Enjoy a dinner nearby as we celebrate a perfect day of cycling.

Meals: Breakfast / Lunch / Dinner
Destinations: Pianella, Bossi, San Felice, San Gusme, Montevarchi, Radda in Chianti
Accomplished: 50 miles / 90 km, elevation gain: 1,250 meters climbing
Accommodations: Borgo di Vescine

Day Six: San Gimignano Loop
Ride out into the Chianti morning toward Castellina, perched above the Elsa Valley. Thrill at the 19-kilometer descent from here to Poggibonsi. Then climb back to the hilltop town of San Gimignano, enjoying a stunning approach as the town’s famous towers come into view. We’ll park our bikes in town then stroll through the medieval streets, enjoy lunch in town, and indulge at the world champion gelateria in the main square. Back on the road, we’ll head south by way of San Donato and Castel San Gimignano before turning for home and climbing back to our hotel through some of Chianti’s largest vineyards. Tonight we’ll celebrate our final dinner at the hotel.

Meals: Breakfast / Lunch / Dinner
Destinations: Castellina, Poggibonsi, San Gimigano, Colle Val d’Elsa
Accomplished: 54 miles / 87 km, elevation gain: 1,116 meters
Accommodations: Borgo di Vescine

Day Seven: Florence
Saddle up for our final ride. Florence is much lower than our hotel, so we will finally get to cash in on all the climbing with a huge net downhill into the Tuscan capital. Along the way, we’ll ride through the heart of Chianti, passing quaint towns such as Panzano and Greve. Outside of Florence we’ll take a series of quiet country lanes as we wind our way up to the city gates. Once inside the walls, most cars are prohibited, and we will pedal through the historic center to finish the trip. Your guides will see you off at the Florence train station.

Meals: Breakfast
Destinations: Panzano, Greve, Florence
Accomplished: 30 miles / 48.5 km, elevation gain: 390 meters