Tuscany Bike Tour

  • Region: Italy
  • Destination: Tuscany
  • Duration: 6 Days / 5 Nights
  • Level: Active
  • Price From: $4695
  • Single Supplement: $ 700
Tour Dates

limited space
Apr 27 - May 2,  2014 $4695 Call to book
May 11 - May 16,  2014 $4695 Book Now
May 18 - May 23,  2014 $4695 Book Now
Jun 22 - Jun 27,  2014 $4695 Book Now
Jun 29 - Jul 4,  2014 $4695 Book Now

View All Dates   Go Private

More Videos

Explore the iconic Italian countryside as you ride through its gentle green hills and cypress lined byways on the Tuscany Bike Tour. Climb into ancient Etruscan villages perched atop vine-covered hills. Discover medieval fortresses and Renaissance masterpieces. You’ll never forget the scent in the air as you ride along the ridges of the Crete Senesi, your visit to Vittorio Innocenti’s private cantina or the sight of the Piazza del Campo at night. Savor local treats like fresh pici pasta, pecorino cheese, and garden fresh bruschetta with local olive oil, and sample the finest Brunello, Super Tuscan, Vino Nobile, and Chianti Classico wines.

Watch Trip Movie

Download Tour | Print |

Tour by Day

Day One: Welcome to Tuscany!
Your guides will meet you at the Chiusi train station, and we’re off to La Chiusa, our first hotel in the sleepy village of Montefollonico. At the hotel, we’ll toast your arrival with a light lunch and Prosecco, then review the essentials: bike fitting and safety talk. Our first ride takes us through the quiet countryside to visit a local olive oil producer. Taste some exceptional local oil before pedaling back to La Chiusa.  Enjoy an après velo cocktail on the patio, surrounded by breathtaking views. Tonight our chef Dania will delight you with gourmet specialties, and our host Umberto will welcome you as a friend and show you how to live like a local.

Meals: Light Lunch / Dinner
Destinations: Montefollonico, Petroio
Accomplished: 14.5 miles / 23.2 km (Longer option: 20 miles/ 32 km)

Day Two: Loop Ride to Pienza
Embark on a loop ride to the town of Pienza. Stop at the gorgeous Renaissance church of San Biagio on the outskirts of Montepulciano before literally pedaling into a postcard.  The cypress-lined curves of our route into Montichiello grace countless local postcards and you’ll see why as we ride by. In fact, this area, known as the Val d’Orcia, is so beautiful that UNESCO has designated it a World Heritage Site.  We’ll take in the views from lunch on a private terrace in Pienza.  Wander the carefully-planned Renaissance streets and sample some local pecorino cheese before looping home to our hotel. Back in Montefollonico, we’ll be treated to a private tour of our friend Vittorio Innocenti’s cantina. Taste his traditional Vino Nobile and Vin Santo in his garden overlooking the Chiana Valley before heading next door for a true feast at our favorite local restaurant.

Meals: Breakfast / Lunch / Dinner
Destinations: Montefollonico, Montepulciano, Montichiello, Pienza
Accomplished: 26 miles / 43 km (Longer option: 36 miles / 59 km)

Day Three: Montalcino: the Land of Brunello Wines
We’re off to discover the land of Brunello wines. Our route takes us through pastures and forests, passing through Trequanda before opening up onto the wheat fields of the Crete Senesi. Ride to the 14th century Abbey of Monte Oliveto Maggiore to visit its outstanding Renaissance frescoes. Enjoy a guided tour of the Abbey followed by a gourmet picnic on the beautiful grounds. From here it is a short ride to our next luxurious hotel. Spend the afternoon relaxing before heading into Montalcino for a cooking class and dinner in the 15th century home of our friends, Domenico and Lina.

Meals: Breakfast / Lunch / Dinner
Destinations: Montefollonico, Trequanda, Monte Oliveto Maggiore, Buonconvento, Montalcino
Accomplished: Shorter option: 25 miles / 40 km (Longer option: 35 miles / 57 km)

Day Four: Along the Crete Senesi
Start the day with a ride through the rolling wheat fields of this scenic landscape. You’ll feel like you’re pedaling through a painting as you pass through Murlo and Vescovado on your way to lunch in the walled town of Asciano. After lunch, opt for a van transfer into Siena or continue riding one of the week’s most stunning rides along the ridges of the Crete Senesi. Climb and descend through Vescona to Arbia, where you’ll again have the chance to stop or continue cycling all the way into the Piazza del Campo in Siena. Tonight you are free to explore the medieval city of Siena.

Meals: Breakfast / Lunch
Destinations: Murlo, Vescovado, Asciano, Vescona, Arbia, Siena
Accomplished: Shorter Option: 20 miles / 32 km; Standard Option: 30 miles / 49 km; Longer Option: 35 miles / 58 km

Day Five: The Hills of Chianti
Pass through rows of olive and cypress trees as we ride deep into the hills of Chianti. Climb above the tree line and ride along a ridge past the gorgeous estates of Bossi and San Felice. We’ll stop at the Castello di Brolio, a landmark for 1000 years, for a tasting of its famous wine. This imposing castle and surrounding vineyards were given a facelift in the nineteenth-century by one of Italy’s first prime ministers, Baron Ricasoli. Continue cycling through vast stretches of Chianti vineyards and winding roads to Radda for lunch. This evening we’ll enjoy an intimate wine tasting and delectable final dinner together.

Meals: Breakfast / Lunch / Dinner
Destinations: Bossi, San Felice, Brolio
Accomplished: 28 miles / 46 km (Longer option: 36 miles / 59 km)

Day Six: Florence
Enjoy your last breakfast in Tuscany and an optional final ride with your guides before shuttling to Florence where we’ll end the tour at the train station of Santa Maria Novella.

Meals: Breakfast 
Accomplished: Optional ride

Related Bike Tours

Super Tuscan Bike Tour         Tuscany 4-Day Bike Tour         Bordeaux Bike Tour