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Assaggio Toscana

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Our six-day “taste” of Tuscany bike tour is the perfect introduction to Italy’s much-loved region of sublime landscapes, divine cuisine, and even finer wines! Welcome to Ciclismo Classico’s long-standing casa in Italy. Starting just above the “argine” or  banks of the Arno in Malva, our tasty Tuscany cycling route follows delightful, twisting roads, past stone-built hamlets, up and over medieval bridges and whizzing through fertile landscapes warmed by the sun. We pedal under the dramatic backdrop of the Pratomagno massif–famed for myriad microclimates–passing tiny, undiscovered 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 with a big splash in dazzling Cortona: a hill-top town gifted with spectacular views brought to life in the acclaimed motion picture, “Under the Tuscan Sun!” A myriad of treasures and surprises 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, known as “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 wine-ing, dining, and relaxing in specially selected luxury accommodations

Tour Essence

  • 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

What to Expect


Flat to Rolling






Average Daily: 26 milesTotal: 130.5 miles


Average Daily: 1,432-2,069 ft Total: 7,159-10,347 ft

DEPARTURE/RETURN LOCATION Italy, Basilicata and Calabria, Puglia
Accommodations & Meals
Professional guide
  • Airfare
  • Gratuity for Ciclismo guides
  • Wine and alcoholic beverages
  • Most lunches
  • Transfers to the starting point; we can assist you in planning and arranging any necessary shuttles
  • Helmets (required)
  • Transport of bike case for guests who bring their own bike (shipping in the destination available for additional fee)
  • Personal expenses such as laundry, supplies, phone calls, etc.



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