Super Tuscany Bike Tour

An Expression of Italian Life at Its Finest

6 days / 5 nights Level: 3Price From: $9,295Collection: Classic

Tour Highlights

  • Stay in one esteemed hotel after another, from a converted castle to an immaculate private estate with its own Brunello winery
  • Ride into the beloved Tuscan hilltowns of San Gimignano, Siena, and Montalcino
  • Learn the family recipes that have been handed down over generations as you cook with our friend Lina at her 15th-century home
  • Pedal through UNESCO-recognized landscapes of wheat fields where scenes from Gladiator were famously filmed
  • Savor true Tuscan hospitality during a home-cooked lunch at our friends’ olive oil mill


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 made from native Sangiovese grapes including Brunello, Chianti Classico, and Vino Nobile; international blends known as Super Tuscans; and—in classic Italian fashion—espresso and cappuccino

Print Itinerary
  • Day 1

    Welcome to Tuscany

    After a private transfer from Florence to your first hotel, your guides will greet you with a light lunch at this private castle. Then we’ll set out on our first ride through the surrounding countryside, with stunning vistas over fields of wheat, sunflowers, and dense oak forests. No ride here is complete without the customary coffee break at a local café, and we will honor this tradition with a stop in the medieval hill town of Casole. Back at the hotel we’ll sample the local wines before our first gourmet dinner prepared by the castle’s chef.

    Meals: Lunch / Dinner
    Destinations: Casole d’Elsa
    Accomplished: 21 miles / 34 km, elevation gain: 1,765 feet / 538 meters
    Accommodations: Castello di Casole

  • Day 2

    San Gimignano

    Wake up to a frothy cappuccino and delectable breakfast before setting out on a ride over the open ridges to San Gimignano. Explore the bustling streets of this famous hill town and climb the tallest remaining medieval tower for one of Tuscany’s most astonishing views. We’ll enjoy lunch at a charming local restaurant, and after you can opt to cycle home or take the van for some relaxation at the hotel. Dinner tonight is a true culinary experience featuring refined Tuscan cuisine at a Michelin-starred restaurant, Arnolfo, in nearby Colle Val d’Elsa.

    Meals: Breakfast / Lunch / Dinner
    Destinations: San Gimignano, Colle Val d’Elsa, San Donato
    Accomplished: 23 miles / 37 km, elevation gain: 2,211 feet / 674 meters
    Longer Option: 46 miles / 74 km, elevation gain: 4,474 feet / 1,364 meters
    Accommodations: Castello di Casole

  • Day 3

    From Casole to Siena

    Say goodbye to the wilds of Casole as we pedal through the forested hills and onto the refined city of Siena. This storied city is like an open-air museum of Gothic architecture, home to prosperous citizens fiercely proud of their traditions like the Palio, a thrilling bareback horse race held in the main piazza. Explore the city and enjoy lunch in the medieval environs of our favorite local restaurant. In the afternoon you can once again opt for an early transfer to our hotel or cycle there through the wheat-covered hills south of Siena. We will spend the next three nights at Massimo Ferragamo’s incredible Castiglion del Bosco hotel. Tonight you can choose to dine here or in the nearby village.

    Meals: Breakfast / Lunch
    Destinations: Siena, Ville di Corsano, Bibbiano
    Accomplished: 40 miles / 65 km, elevation gain: 3,795 feet / 1,157 meters
    Shorter Option: 20 miles / 32 km, elevation gain: 1,745 feet / 532 meters
    Accommodations: Castiglion del Bosco

  • Day 4

    The Crete Senesi

    Wake up to the absolute peace of your tranquil Tuscan villa. Pedal through walled Buonconvento on the way to the Abbey of Monte Oliveto to take in its unique Renaissance fresco. From here the landscape opens up as we ride along the bare ridges of the Crete Senesi, one of the most photographed roads in the world. Lunch is a family affair prepared by our friends Mariella and Paolo at their farmhouse and olive mill outside Castelmuzio. More panoramic views await us on the ride home as well as an optional challenging climb up to the wine-producing village of Montalcino. We’ll all return to Montalcino this evening for a special cooking class and dinner in the 15th-century home of our dear friend Lina.

    Meals: Breakfast / Lunch/ Dinner
    Destinations: Buonconvento, Trequanda, Montisi, Montalcino
    Accomplished: 33 miles / 54 km, elevation gain: 2,654 feet / 809 meters
    Longer Option: 48 miles / 77 km, elevation gain: 3,759 feet / 1,146 meters
    Accommodations: Castiglion del Bosco

  • Day 5

    Val d’Orcia

    Ride this morning from Montalcino and through Italy’s top Brunello vineyards. Stop for a coffee in the medieval heart of San Quirico before heading into the scenic Val d’Orcia, where the iconic wheat field scenes from Gladiator were filmed. Then we’ll ride along the shoulder of Mount Amiata, Tuscany’s towering dormant volcano to lunch and a tasting at our favorite Brunello winery. Stop to take a picture of the beautiful Romanesque Abbey of Sant’Antimo as we pedal back to Montalcino. Our final dinner tonight is at the hotel as we raise a toast to this paradise known as Tuscany.

    Meals: Breakfast / Lunch / Dinner
    Destinations: Montalcino, San Quirico, Sant’Antimo
    Accomplished: 31 miles / 50 km, elevation gain: 3,542 feet / 1,080 meters
    Shorter Option: 26 miles / 42 km, elevation gain: 2,713 feet / 827 meters
    Accommodations: Castiglion del Bosco

  • Day 6

    Ciao to Tuscany

    Say goodbye to Tuscany any way you see fit. Sleep in, stroll around the grounds, or opt for a final early morning ride. Later in the morning, your guides will see you off at the Chiusi Chianciano train station.

    Meals: Breakfast

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: Florence Westin Hotel Pick-Up Time: 10:30 am
Departure Details

Airport City: Rome or Florence, Italy Drop-Off Location: Chiusi Chianciano Train station Drop-Off Time: 10:30 am

Please note that Arrival + Departure Details for 2025 tours could be subject to change.

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

2024Single Supplement From: $5,900

See our cancellation policy

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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
  • 4 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 2 RLE

Manufacturer: Cannondale

Type: Road

Included in trip price

Roadmachine AMP TWO

Manufacturer: BMC

Type: Road E-Bike

$400 supplement, subject to availability

Turbo Vado SL 4.0

Manufacturer: Specialized

Type: Hybrid E-Bike

Included in trip price