Private only

Tuscany Challenge Bike Tour

Terrain and Terroir: Epic Cycling for Epicures

7 days / 6 nights Level: 4Price From: $4,595Collection: Challenge

Tour Highlights

  • Climb Monte Amiata, the 1,753-meter dormant volcano and highest peak in Tuscany
  • Cycle the picture-perfect Crete Senesi, a route lined the waves of golden wheat fields and solitary cypress trees
  • Ride into the beloved Tuscan hilltowns of San Gimignano and Siena
  • Fall in love with our larger-than-life friend, philosopher, and playwright Vittorio over homemade wine at his cantina


Hand-rolled pici pasta, pecorino cheese, olio nuovo (fresh-pressed olive oil), truffles, fava beans, artichokes, chestnuts, porcini mushrooms, Chianina beef, and cinghiale (wild boar)


World-famous wines from the local Sangiovese grape, including Brunello, Chianti Classico, and Vino Nobile; Sangiovese hybrids called Super Tuscans; and—in classic Italian fashion—espresso and cappuccino

Print Itinerary
  • Day 1

    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: Lunch / Dinner
    Destinations: Montepulciano, Montichiello, Orcia Valley, Montefollonico
    Accomplished: 27 miles / 43 km, elevation gain: 2,529 feet / 771 meters
    Accommodations: La Chiusa

  • Day 2

    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: 74 miles / 119 km, elevation gain: 8,331 feet / 2,540 meters
    Shorter Option: 38 miles / 61 km, elevation gain: 6,632 feet / 2,022 meters
    Accommodations: La Chiusa

  • Day 3

    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 / Lunch / Dinner
    Destinations: Trequanda, Asciano, Arbia, Siena
    Accomplished: 50 miles / 80 km, elevation gain: 4,533 feet / 1,382 meters
    Longer Option: 64 miles / 104 km, elevation gain: 4,946 feet / 1,508 meters
    Accommodations: Borgo Grondaie 

  • Day 4

    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 / Lunch
    Destinations: San Casciano, San Galgano, Siena
    Accomplished: 56 miles / 90 km, elevation gain: 5,205 feet / 1,587 meters
    Accommodations: Borgo Grondaie

  • Day 5

    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: 48 miles / 77 km, elevation gain: 5,589 feet / 1,704 meters
    Accommodations: Borgo di Vescine

  • Day 6

    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: 4,799 feet / 1,463 meters
    Accommodations: Borgo di Vescine

  • Day 7


    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. Your guides will see you off at the famous Piazzale Michelangelo.

    Meals: Breakfast
    Destinations: Panzano, Greve, Florence
    Accomplished: 32 miles / 52 km, elevation gain: 2,509 feet / 765 meters

DuVine itineraries may be subject to slight route changes, hotel substitutions, and other modifications.

Arrival Details

Airport City: Rome or Florence, Italy Pick-Up Location: Chiusi Train Station Pick-Up Time: 11:00 am
Departure Details

Airport City: Rome or Florence, Italy Drop-Off Location: Florence Piazzale Michelangelo Drop-Off Time: 1:30 pm
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  • Thoughtfully selected accommodations that reveal the true character of the region in ideal riding locations
  • Luggage transfers


  • Daily breakfasts, all lunches, and 5 cyclist-friendly dinners at our favorite local restaurants and renowned culinary establishments
  • Nutritious energy snacks, hydration, and shakes to support endurance and recovery
  • Local wines and beer with every meal


  • Wine tastings and activities as outlined in the tour itinerary
  • Entrance fees to historic sites, museums, parks, and all other exclusive events
  • Gratuities for baggage, porters, and hotel service


  • Top-of-the-line Cannondale carbon fiber road bike
  • Complimentary DuVine gear, including a custom cycling jersey, DuVine t-shirt, water bottle, and drawstring bag
  • GPS with pre-programmed route maps


  • Expert bilingual guide with extensive cycling experience and local knowledge
  • Support vehicle that follows the day’s route, distributes refreshments, and offers lifts
  • Pick-up and drop-off before and after your tour from predetermined meeting points
  • Laundry service provided mid-week
  • Daily bike maintenance to ensure optimal performance

See our FAQs page for answers to common questions.

See FAQs

Synapse Carbon Disc Ultegra Di2

Manufacturer: Cannondale

Type: Road