Tuscany Bike Tour

Essential Italy: What Locals Love Beyond Siena and Florence

6 days / 5 nights Level: 3Price from: $4,995Collection: ClassicNon-Rider Options

Tour Highlights

  • Learn the family recipes that have been handed down over generations as you cook with our friend Lina at her 15th-century home
  • Ride a loop to Pienza, a place of architectural heritage named for the Pope who made it his mission to transform the town into an ideal Renaissance city
  • Pedal through UNESCO-recognized landscapes of wheat fields where scenes from Gladiator were famously filmed
  • 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, chestnuts, porcini mushrooms, Chianina beef, and cinghiale (wild boar)


Famous local wines, including Brunello, Chianti Classico, and Vino Nobile

Print Itinerary
  • Day 1

    La Dolce Vita

    Meet our guides at the Chiusi train station for a transfer to La Chiusa, a former olive oil mill that is now a charming country inn. The welcome begins with a light lunch and glass of Prosecco, followed by a bike fitting and our first ride into the Tuscan countryside. You’ll feel as though you’ve traveled back to the 13th century while pedaling on the cobbled streets of tiny Petroio and passing generations-old farmers tending their olive groves. Choose your own adventure with longer or shorter ride options. This evening, stroll into the village of Montefollonico for a winetasting with our friend Vittorio and an incredible Tuscan dinner.

    Meals: Lunch / Dinner
    Destinations: Montefollonico, Petroio
    Accomplished: 20 miles / 32 km, elevation gain: 450 meters
    Shorter Option: 15 miles / 24 km, elevation gain: 238 meters
    Accommodations: La Chiusa

  • Day 2

    Montalcino: Castles, Brunello, and Home-Cooking

    Set off riding through pastures and forests to join the locals for a coffee in sleepy Montisi. Take in panoramic views of the bare ridgelines of the Crete Senesi and pedal down the Asso Valley into the Brunello wine-growing region. It’s a big climb up to Montalcino, the medieval hilltown at the heart of the Brunello zone, but the effort is well-rewarded with a tasting lunch at our favorite winery. Spend the afternoon relaxing by the pool or getting pampered at the spa of our five-star castle hotel. This evening we’ll head back into Montalcino for a cooking class and dinner in the 15th-century home of our friend Lina.

    Meals: Breakfast / Lunch / Dinner
    Destinations: Montefollonico, Montisi, Torrenieri, Montalcino
    Accomplished: 33 miles / 53 km, elevation gain: 583 meters
    Accommodations: Castello di Velona

  • Day 3

    Pienza Loop: The Renaissance Ride

    Embark on a loop ride to the town of Pienza, then climb up to Castiglione with its medieval fortress for a well-earned break. Descend into the Val d’Orcia, an area so beautiful that UNESCO designated it a World Heritage Site and the movie Gladiator’s famous wheat field scene was filmed here. Take in sprawling views during lunch on a private terrace in Pienza, then wander the carefully laid-out Renaissance streets. After a taste of some local Pecorino cheese, it’s time to complete the loop home to our hotel for another luxurious evening.

    Meals: Breakfast / Lunch / Dinner
    Destinations: Castiglione d’Orcia, Pienza, San Quirico d’Orcia
    Accomplished: 26 miles / 42 km, elevation gain: 650 meters
    Longer Option: 43 miles / 69 km, elevation gain: 699 meters
    Accommodations: Castello di Velona

  • Day 4

    Across the Crete Senesi: Monks and Masterpieces

    Say goodbye to the Castello di Velona as we ride through the mystical morning light that bathes the Romanesque Abbey of Sant’Antimo. Pedal across the Brunello region before we stop for a visit of the Renaissance frescoes at the Abbey of Monte Oliveto. After a picnic lunch, continue riding along the open ridges of this scenic landscape. Opt for an earlier van transfer or continue cycling all the way to our final hotel, the Relais & Chateaux Borgo San Felice. Tonight, head into the medieval city of Siena to explore and dine there, or opt to dine at the hotel.

    Meals: Breakfast / Lunch
    Destinations: Buonconvento, Monte Oliveto, Asciano, Siena
    Accomplished: 27 miles / 44 km, elevation gain: 923 meters
    Longer Option: 47 miles / 76 km, elevation gain: 641 meters
    Accommodations: Borgo San Felice or Le Fontanelle

  • Day 5

    Chianti Classico: The Tuscan Heartland

    Olive and cypress trees surround us as we ride deep into the hills of Chianti. We’ll see plenty of fortified hamlets and castles—relics of Florence and Siena’s 300-year struggle for regional dominance and ownership over the origin of Chianti Classico wines found in ancient cellars around the area. Pedal past countless estates as we weave our way through forests and vineyards to lunch with our friend Max at his innovative bistro. After lunch, opt for a longer ride or a straight shot back to the hotel. We’ll regroup in the evening for a tasting of San Felice’s famous wines and a festive final dinner.

    Meals: Breakfast / Lunch / Dinner
    Destinations: Castelnuovo, Brolio, Castagnoli
    Accomplished: 31 miles / 50 km, elevation gain: 568 meters
    Longer Option: 37 miles / 60 km, elevation gain: 562 meters
    Accommodations: Borgo San Felice or Le Fontanelle

  • Day 6

    Ride to Florence

    On our last day, choose between a late morning at the hotel or ride all the way across Chianti for a triumphant finish in Florence’s Piazzale Michelangelo. Whether you rode here or took a transfer, we say our goodbyes with the stunning Florentine skyline as our backdrop as guides see you off to your next adventure.

    Meals: Breakfast
    Destinations: Panzano, Greve, Florence
    Optional Ride: 30 miles / 48 km, elevation gain: 658 meters
    Longer Option: 42 miles / 68 km, elevation gain: 543 meters

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

Airport Information


Airport City: Rome or Florence, Italy
Pick-Up Location: 11:00am at the Chiusi Train Station


Airport City: Rome or Florence, Italy
Drop-Off Location: 1:30pm at Florence Piazzele Michelangelo

Any scheduled tour can be made private. Your group, your dates.     Go Private

2018Single Supplement From: $950

See our cancellation policy


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


  • Daily breakfasts, all lunches, nutritious snacks, and après velo cocktails
  • 4 gourmet dinners at our favorite local restaurants and renowned culinary establishments
  • Carefully selected local wines with every meal


  • Top-of-the-line bicycle selection and 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


  • 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

Not Included

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Quick SPEED 1

Manufacturer: Cannondale

Type: Hybrid

Synapse Carbon Ultegra Di2

Manufacturer: Cannondale

Type: Road


Type: E-wheel


Type: E-Bike