Tuscany 4-Day Bike Tour

A Taste of Tuscany: Shorter and Just as Sweet

4 days / 3 nights Level: 1Price From: $3,595Collection: Classic

Tour Highlights

  • Ride surrounded by olive groves, cypress trees, sunflower fields, and bucolic cow pastures
  • Meet the locals as we learn to cook a Tuscan lunch with our friend Barbara and her mother at their beautiful Farmhouse
  • Taste exquisite vintages during a private wine-paired lunch at our favorite local winery
  • Pedal along the shores of Lake Trasimeno in the silent stillness of the Val di Chiana


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

    Meet your guides at the Chiusi train station for a transfer to the medieval village of Montefollonico where the adventure begins. We’ll toast our arrival with a light lunch at our favorite local restaurant. After a bike fitting and safety review, we’ll set off on our first ride through the Tuscan countryside past cows, sheep, olive groves, and vineyards. Enjoy views over the gorgeous Chiana and Orcia valleys as we gradually descend to our hotel, once a small village that has been beautifully converted. We’ll celebrate tonight with a dinner featuring homemade pastas, fresh seasonal vegetables, and, of course, a selection of local wines.

    Meals: Lunch / Dinner
    Destinations: Montefollonico, Trequanda, Sinalunga
    Accomplished: 17 miles / 28 km, elevation gain: 328 meters
    Longer Option: 30 miles / 47 km, elevation gain: 671 meters
    Accommodations: Locanda dell’Amorosa

  • Day 2

    Sinalunga to Cortona

    Cycling out of Sinalunga, we’ll make our way across the Val di Chiana, home of Tuscany’s famed white Chianina cows. Cypress trees, sunflowers, and wheat fields line our route as we pedal deep into the countryside. Learn how to make fresh pasta during a stop for lunch at our friend Barbara’s local farmhouse; our meal will feature fresh, seasonal ingredients straight from the farmhouse’s very own garden. We’ll leave feeling part of the family. Opt to ride or transfer to our next luxurious villa hotel. This evening we’ll head into Cortona, an ancient hill town with Etruscan walls and a medieval core. Wander the streets, take in the gorgeous views of the valley below, and explore the bustling artisanal shops before dinner at a local restaurant we love.

    Meals: Breakfast / Lunch / Dinner
    Destinations: Val di Chiana, Foiano, Cortona
    Accomplished: 26 miles / 42 km, elevation gain: 395 meters
    Shorter Option: 19 miles / 31 km, elevation gain: 253 meters
    Accommodations: Il Falconiere Relais

  • Day 3

    Lake Trasimeno

    Pedal from Cortona through the olive groves to the blue waters of Lake Trasimeno, site of one of Hannibal’s greatest victories over the Romans. We visit Villa Loggio winery, an estate dating back to 1676, for a private tasting lunch with some of Tuscany’s top wines. Afterwards, complete the bike loop back to the hotel or opt for a quick shuttle back to relax and enjoy the pool and spa. This evening we’ll end our journey in style with a final dinner at the hotel’s Michelin-starred restaurant.

    Meals: Breakfast / Lunch / Dinner
    Destinations: Lake Trasimeno, Villa Loggio, Barullo
    Accomplished: 32 miles / 51 km, elevation gain: 516 meters
    Shorter Option: 22 miles / 35 km, elevation gain: 385 meters
    Accommodations: Il Falconiere Relais

  • Day 4


    Say goodbye to Tuscany however you see fit. Sleep in, challenge yourself with an optional morning loop ride, or enjoy a leisurely breakfast on the terrace. Your guides will see you off from the train station in Cortona.

    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: Chiusi Train Station Pick-Up Time: 11:00 am
Departure Details

Airport City: Rome or Florence, Italy Drop-Off Location: Terontola Cortona Train Station Drop-Off Time: 12:00 pm

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

2020Single Supplement From: $650

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
  • 3 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.

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Quick 1 Disc

Manufacturer: Cannondale

Type: Hybrid

Quick Neo

Manufacturer: Cannondale

Type: E-Bike

Synapse Carbon Ultegra Di2

Manufacturer: Cannondale

Type: Road