Private only

Tuscany Villa Bike Tour

A Countryside Ride Retreat

6 days / 5 nights Level: 3Price From: $5,495Collection: ClassicNon-Rider Options

Tour Highlights

  • Unpack once and enjoy an incredible week of riding from the same luxurious home base
  • Tailor your itinerary to your unique interests—including hiking, cooking classes, wine tastings, private yoga classes, and more—perfect for groups with mixed riding levels
  • Discover Tuscany’s cultural facets by bicycle, from Renaissance art and architecture to wine tastings and one-on-one time with locals
  • Dine on a thoughtful blend of cyclist-friendly fare prepared by the villa’s private chef and essential dishes in classic Tuscan restaurants


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

As featured in:
Print Itinerary
  • Day 1


    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.  First order of business: a home-cooked lunch prepared by our hosts, Johny and Rita, designed to power us through our first ride. After a bike fitting and safety talk, we’ll set off on a warmup loop along the ridges of the Crete Senesi followed by a long, gradual climb to the heights of Collalto, returning home via Trequanda. Back at the villa, take a dip in the pool while the villa’s chef works some magic on our first Tuscan dinner.

    Non-riders can relax at the villa or head to a local olive mill for an organic olive oil tasting.

    Meals: Lunch / Dinner
    Destinations: Asciano, Collalto, Trequanda
    Accomplished: 27 miles / 43 km, elevation gain: 2,043 feet / 623 meters
    Shorter Option: 17 miles / 27 km, elevation gain: 1,325 feet / 404 meters
    Accommodations: Podere Ferranesi

  • Day 2

    The Crete Senesi: White Roads and Renaissance Masterpieces

    Today we tackle a classic loop over the low, cypress-punctuated hills of the Crete Senesi. This area is historically known as the breadbasket of Siena, an identity that comes to life as we pedal up and down the ridges of open grassland. You may also recognize the region as host of the Strade Bianche—a daylong race on these “white roads,” taking place each March—particularly when we cross the race route multiple times. Return to the villa in time for lunch by the pool or admire Renaissance frescoes at the nearby Abbey of Monte Oliveto. Tonight, the chef will wow us once again us with a meal designed to fuel the rides that lie ahead.

    Non-riders can spend the day at the villa, visit the Monte Oliveto frescoes, and join the group for lunch in Buonconvento.

    Meals: Breakfast / Lunch / Dinner
    Destinations: Asciano, Monteroni, Buonconvento
    Accomplished: 37 miles / 59 km, elevation gain: 3,182 feet / 970 meters
    Shorter Option: 21 miles / 34 km, elevation gain: 1,322 feet / 403 meters
    Longer Option: 49 miles / 79 km, elevation gain: 4,697 feet / 1,432 meters
    Accommodations: Podere Ferranesi

  • Day 3

    The Val d’Orcia, Pienza, and Truffle Hunting

    Another day, another beautiful ride through the backdrops of Tuscany beloved by Hollywood. First up is Montepulciano, recently featured in Twilight and Masters of Florence, then out into the Val d’Orcia, where Gladiator’s iconic wheat field scenes were filmed. Our last stop is for lunch in Pienza, the setting for The English Patient. Dine on the terrace of a former cloister before completing the loop back to our villa. This evening, our friend Paolo and his faithful truffle dog help us hunt for the perfect morsel, which we’ll taste at our friend Donatella’s cozy osteria—just one feature of this truffle-themed feast.

    Non-riders can visit a farm outside of Pienza where they’ll learn to bake rustic Tuscan bread or make cheese, then explore shops and cafés in the hill towns of Montepulciano and Pienza before meeting the riders for lunch.

    Meals: Breakfast / Lunch / Dinner
    Destinations: Montepulciano, Montichiello, Pienza
    Accomplished: 35 miles / 56 km, elevation gain: 3,057 feet / 932 meters
    Shorter Option: 18 miles / 29 km, elevation gain: 1,496 feet / 456 meters
    Longer Option: 49 miles / 79 km, elevation gain: 4,848 feet / 1,478 meters
    Accommodations: Podere Ferranesi

  • Day 4

    Local All the Way (Featuring Brunello di Montalcino)

    This morning will find us pedaling past the Abbey of Monte Oliveto, onto the ancient Roman road, the Via Cassia, and up to the perched town of Montalcino. Nearly abandoned during the post-war economic boom, Montalcino has enjoyed a renaissance due to the popularity of Brunello wines that, by law, can only be produced here. We’ll ride the entire length of this now-famous wine region and pause for a tasting lunch. After lunch, choose to shuttle back to the villa or keep climbing up to Castiglione d’Orcia before looping back home via San Quirico. Tonight, we return to Montalcino for a truly Tuscan affair: an evening of cooking, drinking, and learning to live like a local with our friend Lina in her 15th-century home.

    Non-riders can go for a horseback ride in the hills near the villa, spend the day at the natural thermal hot springs of Bagno Vignoni, visit a local Brunello producer for a tasting, or do all three!

    Meals: Breakfast / Lunch / Dinner
    Destinations: Montalcino, Castiglione d’Orcia, San Quirico
    Accomplished: 52 miles / 84 km, elevation gain: 5,146 feet / 1,569 meters
    Shorter Option: 24 miles / 38 km, elevation gain: 2,211 feet / 674 meters
    Accommodations: Podere Ferranesi

  • Day 5

    Battlefields, Castles, and Chianti Classico

    No trip to Tuscany is complete without a visit to Chianti. To get there, we’ll ride one of the most-photographed roads in the world, once again crossing into Strade Bianche territory. You’ll know you’re in Chianti when the wheat fields give way to vineyards and deep, cool forests. It was here in Montaperti that a desperate Sienese army shocked the medieval world with its victory over Florence in 1260, paving the way for Siena’s golden age. The 300 years of intermittent warfare that followed resulted in the fortified towns and countless castles that pepper the entire region. We’ll stop for coffee in Castelnuovo (appropriately meaning “New Castle”) before finishing the ride home through Rapolano. Tonight, our final dinner celebrates a successful week—did someone say pizza oven?

    Non-rider options can head to the city of Siena to soak up medieval architecture, shop, museum-hop, or take a fascinating guided tour that focuses on the Palio, Siena’s famous bareback horse race. Or, visit a historic castle and wine producer in Chianti for an incredible tasting lunch.

    Meals: Breakfast / Lunch / Dinner
    Destinations: Montaperti, Castelnuovo Berardenga, Rapolano
    Accomplished: 47 miles / 75 km, elevation gain: 3,601 feet / 1,098 meters
    Shorter Option: 25 miles / 41 km, elevation gain: 2,181 feet / 665 meters
    Accommodations: Podere Ferranesi

  • Day 6


    It’s your last day in Tuscany, so how to spend it is up to you: sleep in, or elect to take a final ride through the surrounding hills. Your guides will return you to the Chiusi train station, bidding you farewell as you head on to your next destination.

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

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

Arrival Details

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

Airport City: Rome or Florence Drop-Off Location: Chiusi Train Station Drop-Off Time: 10:30 am

This itinerary lends itself beautifully to customization and can be tailored to any riding level—including families or mixed groups with non-riders. Choose from activities that interest your group, whether they’re foodies seeking to hit all the best osterias or serious cyclists who want a massage therapist on call for daily massages.

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  • Thoughtfully selected accommodations that reveal the true character of the region
  • Luggage transfers


  • Daily breakfasts, all lunches, nutritious snacks, and après velo cocktails
  • 5 gourmet dinners at our favorite local restaurants and renowned culinary establishments
  • Carefully selected local wine, beer, or spirits 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 bicycle selection
  • Bike helmet
  • Complimentary DuVine gear, including a custom cycling jersey, DuVine t-shirt, water bottle, and drawstring bag
  • GPS in most destinations


  • Expert bilingual guides with extensive 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
  • 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

Quick 1 Disc

Manufacturer: Cannondale

Type: Hybrid

Quick Neo

Manufacturer: Cannondale

Type: E-Bike