Tuscany 4-Day Bike Tour

  • Region: Italy
  • Destination: Tuscany
  • Duration: 4 days / 3 nights
  • Level: One
  • Price From: $3295
  • Single Supplement: $500
Tour Dates
Apr 9 - Apr 12, 2017 $3295 Book Now
May 14 - May 17, 2017 $3295 Book Now
Jun 4 - Jun 7, 2017 $3295 Book Now
Jul 2 - Jul 5, 2017 $3295 Book Now
Aug 20 - Aug 23, 2017 $3295 Book Now

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Explore the iconic Tuscan countryside as you ride through its gentle green hills and cypress-lined byways on this 4-Day Tuscany Bicycle Trip. Travel through history in the Chiana Valley, the crossroads of Italy, traversed by countless armies, popes, emperors, and artists. Get intimately familiar with the local cuisine at a cooking class in our friend Barbara’s farmhouse. Stroll the ancient streets of Etruscan Cortona, pedal through fields of sunflowers, and discover your inner gourmet during a paired lunch and winetasting at an acclaimed local winery. Cap off every day in style with accommodations in the most luxurious Tuscan villas.


Tour by Day

Day One: 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: Light Lunch / Dinner
Destinations: Montefollonico, Trequanda, Sinalunga
Accomplished: 15 miles / 24 km, elevation gain: 234 meters (Longer option: 25 miles / 40 km)
Accommodations: Locanda dell’Amorosa

Day Two: 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 to taste fresh seasonal cuisine; our meal will come 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. Regroup later in the evening for dinner in the garden as we savor the flavors of Tuscany.

Meals: Breakfast/ Lunch/ Dinner
Destinations: Val di Chiana, Foiano, Cortona
Accomplished: 20 miles / 32 km with 287 meters (Longer option 32 miles / 51.5 km, elevation gain: 372 meters)
Accommodations: Villa di Piazzano

Day Three: Lake Trasimeno
Pedal from Cortona through the olive groves to the blue waters of Lake Trasimeno and stop for a visit to Villa Loggio, an estate dating back to 1676. Tour the cellar before settling down for a tasting lunch with some of Tuscany’s top wines. Ride back to the hotel to relax or opt for an extra bike ride. This evening we’ll head into Cortona, an ancient hilltown with Etruscan walls and a medieval core. Wander the streets, take in the gorgeous views to the valley below, and explore the bustling artisanal shops before dinner at our favorite local restaurant to celebrate the end of a fantastic tour.

Meals: Breakfast / Lunch / Dinner
Destinations: Lake Trasimeno, Villa Loggio, Barullo
Accomplished: 23 miles / 38 km, elevation gain: 288 meters (Longer option: 40 miles / 56 km, elevation gain: 384 meters)
Accommodations: Villa di Piazzano

Day Four: Arrivederci
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
Accomplished: Optional ride