Tuscany 4-Day Bike Tour

  • Region: Italy
  • Destination: Tuscany
  • Duration: 4 days / 3 nights
  • Level: Occasional
  • Price From: $3295
  • Single Supplement: $500
Tour Dates
Apr 10 - Apr 13, 2016 $3295 Book Now
May 15 - May 18, 2016 $3295 Book Now
Jun 26 - Jun 29, 2016 $3295 Book Now
Jul 31 - Aug 3, 2016 $3295 Book Now
Aug 21 - Aug 24, 2016 $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, a crossroads of Italy traversed by countless armies, popes, emperors, and artists. Get intimately familiar with the local cuisine at a cooking class  in Cortona. On this four-day bike tour in Tuscany, you’ll get the perfect taste of one of Italy’s most storied regions. Discover your inner gourmet at a paired lunch and winetasting at one of Italy’s most highly-acclaimed wineries and relax completely in the most luxurious villas.


Tour by Day

Day One: Welcome to Tuscany
Your guides will greet you at the Chiusi train station and transfer you 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: 334 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. Stop for lunch at a local farmhouse to taste fresh seasonal cuisine; our meal will come straight from the farmhouse’s very own garden. You will leave our friend Barbara’s house feeling part of the family before continuing to our hotel at the foot of Cortona. This evening we’ll head into Cortona, a perfectly kept medieval town perched on a hilltop with gorgeous views to the valley below. We will leave you to explore the bustling artisan shops and piazzas before dinner at our favorite local restaurant.

Meals: Breakfast/ Lunch/ Dinner
Destinations: Val di Chiana, Foiano, Cortona
Accomplished: 23 miles / 37 km, elevation gain: 383 meters (Longer option: 34 miles / 55 km)
Accommodations: Relais Il Falconiere

Day Three: Lake Trasimeno

Pedal from Cortona through the olive groves to the blue waters of Lake Trasimeno, where Hannibal famously ambushed the Roman army in 217 BC. Fortunately the locals now make wine, not war. We will take full advantage of this with a visit to Villa Loggio, the 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, learn the art of Italian hospitality during a cooking class with a local chef featuring the best local ingredients and recipes.

Meals: Breakfast / Lunch / Dinner
Destinations: Lake Trasimeno, Villa Loggio, Barullo
Accomplished: 27 miles / 44 km, elevation gain: 491 meters (Longer option: 40 miles / 66 km)
Accommodations: Relais Il Falconiere

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