Assaggio Toscana Bike Tour

Savor a “taste” of Tuscany as we bike through the glorious heart of Italy.

Our six-day “taste” of Tuscany bike tour is the perfect introduction to Italy’s much-loved region of sublime landscapes, fine cuisine, and even finer wines! Starting on the banks of the Arno in Malva, our Tuscany cycling routes follow delightful, twisting roads, past stone-built hamlets, and through fertile landscapes warmed by the sun. We pedal through the dramatic Pratomagno mountains, famed for their myriad microclimates, passing tiny historic towns as we cruise down byways lined with cypress trees and flanked by ripening vineyards.

On the Sette Ponti (Seven Bridges) road, we’ll cross the Ponte a Buriano, renowned as the rustic backdrop to the Mona Lisa’s enigmatic smile. Along the way, you’ll get to savor the best of the region’s cuisine, attend authentic Tuscan wine tastings, and visit ancient Etruscan ruins. Our magical Tuscany cycling adventure ends in Cortona, a hill-top town gifted with spectacular views, which was brought to life in the acclaimed motion picture, “Under the Tuscan Sun!”

A myriad of treasures await you on this unforgettable Tuscany cycling tour.

You’ll be immersed in the history, heritage, and mystique of this alluring land, as our Tuscany bike tour winds through the region’s exquisite landscapes. Our biking route takes in medieval Loro Ciuffenna, with its elegant gorge-spanning bridge, the fortified village of Lucignano, and the Renaissance gem that is Arezzo. Known for its many artistic treasures, Arrezzo was the beautiful backdrop for the Oscar Winning Film “La Vita e’ Bella” (Life is Beautiful).

Crossing the border into Umbria, the “Green Heart of Italy,” our cycling adventures take us to the deep-blue waters of Lago Trasimeno, where we’ll see the site of the epic clash of Hannibal and his elephants with the Roman legions. Along the way, we’ll learn how Tuscan vintners create world-class wines and explore Roman ruins, Etruscan tombs, and Renaissance palaces. Each day’s biking in Tuscany will end with wining, dining, and relaxing in specially selected luxury accommodations.


  • Tuscany cycling routes that pass through numerous vineyards in one of the world’s finest wine regions
  • Cruise through charming rural landscapes flanking the historic Sette Ponti Road
  • Discover the delights of Tuscan olive oil with a special tasting tour
  • Delve into ancient history in the land of the Etruscans
  • Enjoy an authentic Tuscan wine tasting

Trip Details

Single Supplement
6 days / 5 nights
Athletic Beginner
Total Mileage
130.5 miles
Daily Average
26 miles
Rolling with some flatland
Start/End Locations
Trip Dates
05/13/19 - 05/18/19
06/03/19 - 06/08/19
06/10/19 - 06/15/19
06/24/19 - 06/29/19
07/15/19 - 07/20/19
07/29/19 - 08/03/19
09/02/19 - 09/07/19
09/16/19 - 09/21/19
09/23/19 - 09/28/19
10/07/19 - 10/12/19

Make this tour Private or for more information, call:



Malva to Loro Ciuffenna

Welcome to Italy! Your Tuscan adventure will begin at the San Giovanni Valdarno train station, where our guide will meet you at 12 pm and provide a shuttle to our first hotel. A light lunch will be waiting for you in the hotel restaurant after you get settled in. In the afternoon after our bike fitting and safety talk, we’ll warm up with a ride to Loro Ciuffenna and visit one of the oldest operational water mills in Tuscany. The extra loopers will pedal to le Balze di Piantravigne.

Loop to Reggello

After breakfast we’ll pedal through the dramatic sun-drenched Pratomagno range where micro-climates flourish. We will stop and visit castello dei Bonsi for an olive oil tour and tasting. Lunch will be in Reggello, in a vegan/vegetarian bistrot. The extra loopers will pedal to le Balze di Piantravigne, a unique landscape formed by rivers flowing from the Apennines, and the Parco Carabè for an artisan gelato. The normal loopers will have a delightful, easy ride on “Via dei Sette Ponti,” an old Roman road connecting Firenze and Arezzo. Tonight before dinner, we’ll have an Italian lesson.

Malva to Arezzo

Today will be a feast for all the sense as we make our way to the Renaissance gem of Arezzo. Ride to the Ponte Buriano, made famous by Leonardo da Vinci‘s background on the Monna Lisa. In the afternoon we’ll have a guided walking tour of the town of Arezzo, the backdrop for the Oscar-winning film “La Vita e’ Bella” (Life is Beautiful). Tonight will be a free night to explore the restaurants and cafes of lively Arezzo on your own.

Arezzo to Cortona

Cycle the flatlands of La Val di Chiana through Italy’s famous sunflower fields and beautiful wheat fields. Our destination is Cortona, an exquisite hill town filled with Etruscan treasures. We’ll stop for a delicious picnic lunch and wine tasting at the Santa Vittoria vineyard estate. A late afternoon guided walking tour of Cortona will lead us to Roman arches, Etruscan tombs, and Renaissance palaces. Tonight is pizza night at our favorite local pizzeria!

Loop to Castiglione del Lago

Cross the border to the Green Heart of Italy—Umbria—where the terrain rolls through several small villages. We’ll take a short ride along a very charming lake and we’ll walk along the Palazzo della Corgna, a 16th-century ducal palace housing frescoes by Giovanni Antonio Pandolfi and Salvio Savini. Before lunch, we’ll stop to visit a local bike shop where you can purchase Italian-made cycling gear and souvenirs. After lunch, you can either shuttle back to Cortona or get a few more miles under your belt and bike back to Cortona. We’ll have lunch at our friends Gabriele and Maria Grazia’s private home, where they’ll teach you how to make pici, a thick Italian spaghetti that’s very famous in Tuscany.


Why not extend your Tuscan journey for a few extra days to see Florence’s Renaissance treasures, or experience a typical agriturismo where to plan your next tour in another part of Tuscany?
Today after breakfast around 9 am, we'll 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.

Ciclismo Assaggio Trip Map

What's Included

Trip Planning

  • Use of carbon road bike, fully-equipped with a Garmin Edge Touring GPS
  • Informative tour leaders on-hand throughout the Ciclismo Classico tour
  • Ciclismo jersey and water bottle
  • Shuttles at both the beginning and the end of the tour

On The Tour

  • Van support
  • 1 wine tasting
  • 1 olive oil tasting
  • 1 cooking demonstration
  • Guided walking tours of Arezzo and Cortona

Accomodations & Meals

  • All accommodations
  • All breakfasts
  • 2 lunches + 1 picnic
  • 4 dinners

Meet the Guides