Assaggio Toscana

Savor “A Taste of Tuscany” as we Tour the Heart of Italy by Bike!

Our six-day, entry-level assaggio, or “tasting,” of Tuscany cycling tour is the perfect introduction to Italy’s beloved central region! Commencing in the terraced foothills of upper Val d’Arno on the river Arno, our route follows delightful, twisting roads, cooled by breezes in stone villages, and through fertile landscapes warmed by the famous Tuscan sun. We pedal through the dramatic Pratomagno range with their myriad microclimates, and tiny towns along byways lined with fig trees, vegetable gardens and vineyards. On the Sette Ponti (Seven Bridges) Road, we’ll cross the Ponte a Buriano, centerpiece of the background of the Mona Lisa, painted by Leonardo da Vinci. Along the way savor the best of Tuscan cuisine and regional specialties, attend authentic Tuscan wine tastings, visit Etruscan ruins and much more before we conclude our bike trip in the storybook medieval village of Cortona, brought to life in the acclaimed motion picture, “Under the Tuscan Sun!”

Tuscany’s Treasures Await on this Unforgettable Cycling Tour

Immerse yourself in the history, the heritage and the mystique of Tuscany as our bike tour wends through the region’s enchanting landscapes. Our route includes the lovely town of Loro Ciuffenna, the fortified village of Lucignano, and the Renaissance gem of Arezzo with its many artistic treasures, backdrop for the Oscar Winning Film “La Vita e’ Bella” (Life is Beautiful). Crossing the border into the “Green Heart of Italy” – Umbria and the blue waters of Lago Trasimeno – we’ll see where Hannibal and his elephants met Romans legions in epic battle. Along the way we’ll learn how Tuscan vintners combine modern technology with traditional methods to create world-class wines, and explore Roman ruins, Etruscan tombs, and Renaissance palaces, while relaxing at the end of each day in luxury accommodations. This is European bicycle touring at its best!


  • Discover Tuscan olive oil
  • Vineyard views galore!
  • Spin along the delightful Sette Ponti Road
  • Visit the land of the Etruscans
  • Authentic Tuscan wine tasting

Trip Details:

Biking Classics

Price: $3,495
2016: $3,795

Single Supplement: $600

Length: 6 days / 5 nights

Level: Athletic Beginner

Total Mileage: 147 miles

Daily Average: 30 miles

Terrain: Rolling, some flatland

Start/End Locations: San Donato/Cortona

Trip Dates:

  • 09/14/15 - 09/19/15
  • 09/21/15 - 09/26/15
  • 10/05/15 - 10/10/15
  • 05/16/16 - 05/21/16
  • 06/06/16 - 06/11/16
  • 06/13/16 - 06/18/16
  • 06/20/16 - 06/25/16
  • 07/11/16 - 07/16/16
  • 09/05/16 - 09/10/16
  • 09/19/16 - 09/24/16
  • 10/03/16 - 10/08/16
  • 10/17/16 - 10/22/16

= Sold Out

Make this tour Private or for more information, call:


Day by Day

San Donato

Today take our group shuttle at 12pm in Figline Valdarno train station or meet us at the hotel around 1pm for a light lunch and introductions. In the afternoon we'll warm up on a ride with a few hills through olive groves and amidst stone villas, providing a great orientation to the sights and sounds of the area. Don’t let this hilly warm up ride discourage you - tomorrow you’ll easily manage your bike and gears on the sweet Tuscan hills!

Loro Ciuffenna

The zigzagging continues as we pedal through the dramatic sun-drenched Pratomagno range where microclimates flourish. Tiny towns are linked along this lovely road lined with fig trees, vegetable gardens, and vineyards. Today we’ll visit an olive oil press and we’ll taste the finest Olio d’Oliva. Don’t forget to take a walk in the lovely town of Loro Ciuffenna, where we'll stop for lunch.


Along the way to the Renaissance gem of Arezzo we’ll have the option of visiting Il Borro, a charming small village owned by the Ferragamo family, and we’ll ride to the Ponte a Buriano, that Leonardo da Vinci painted on the background of the Mona Lisa. In the afternoon we’ll have a walking tour of Arezzo’s many artistic treasures - Arezzo hosts the works of Piero della Francesca and is the heartwarming backdrop for the Oscar Winning Film “La Vita e’ Bella” (Life is Beautiful).


The flatlands of La Val di Chiana ease our velo voyage to Cortona, an exquisite hill town filled with Etruscan treasures. Don’t miss the stop in the enchanting fortified village of Lucignano, shortly before our picnic lunch and wine tasting at the Santa Vittoria estate - where they blend modern knowledge with the wisdom of tradition to obtain unique wines. A late afternoon walking tour of Cortona leads us to Roman arches, Etruscan tombs, and Renaissance palaces.

Lake Trasimeno

Cross the border into the Green Heart of Italy - Umbria and the blue waters of Lago Trasimeno, where Romans lost their lives to Hannibal’s attacks and his elephants. The flat terrain rolls through wheat and sunflower fields and it dips up and down through several small villages. As it’s a favorite route for local cyclists, be sure to say “SALVE” (greetings)!


Why not extend your Tuscan journey for a few extra days to see Florence’s Renaissance treasures? Today, after breakfast, around 9am we will shuttle you to Cortona’s train station and we are happy to assist you with any post tour travel needs, whether you are continuing on to a new city or returning to Florence.

What's Included

Trip Planning

  • Bike rental equipped with odometer, map case, handlebar and seat bags and bike pump.
  • Ciclismo jersey and water bottle
  • Shuttles at beginning and end of tour

On The Tour

  • 1 Tour of olive oil press and tasting
  • 1 Wine tasting and 1 cooking demonstration
  • Walking tours of Arezzo & Cortona
  • Daily cycling coaching

Accommodations & Meals

  • All accommodations
  • All breakfasts
  • 4 dinners
  • 1 light lunch
  • 1 picnic
Here’s a sampling of some of the amazing places you’ll stay on your journey.

For a full listing, request a detailed itinerary!

Fattoria degli Usignoli

Fattoria degli Usignoli means "Farm of the Nightingales" and was built in the 1400s by the friars of Vallombrosa. You can still see many traces of its history inside. At 400m above sea level, it’s as wonderful as the surrounding countryside. Amenities include a swimming pool, archery, tennis courts, horseback riding, and hiking trails. Their restaurant serves delicious, authentic Tuscan meals.
View their website

Vogue Hotel Arezzo

Located in the heart of the city, Vogue Hotel Arezzo is perfect for conducting business or enjoying the sights of the city. It is also the premier choice among hotels in town. The hotel’s high-impact design and dedication to service creates a one-of-a-kind hotel experience in Arezzo. The hotel offers 26 exceptional rooms, all with a different design and layout that make each experience unique.
View their website

Villa Marsili

Villa Marsili is situated inside the town walls. The villa dates back as far as late '700 and the present owners have restored all original style details and architectural characteristics lost through centuries of previous interventions.
View their website

Meet the Guides