Taste of Tuscany
with a dash of Umbria
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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
Terrain
Flat to RollingStart Location
San Giustino ValdarnoEnd Location
CortonaMileage
Average Daily: 26/33 miles Total: 130/168 milesElevation
Average Daily: 1,391/2,094 ft Total: 6,955/10,474 ftOnce you have a trip confirmed, we will feed you a steady diet of additional pre-departure information that includes: How to train, prepare, pack and all the wonderful, inspirational and practical things you want and need to know before you go! Our Travel Advisors will be available to help plan your pre- and post-tour travel.
- Van support
- Expert, bilingual guides
- 1 wine tasting
- 1 olive oil tasting
- 1 cooking demonstration
- Guided walking tours of Arezzo and Cortona
- Shuttles at both the beginning and the end of the tour
What’s Included
- Use of our exclusive carbon road bike, La Classica Ribelle (or Equivalent Carbon Road Bike)
- Garmin Edge Explore GPS loaded with the GPX tracks of your rides
- Two water bottles
- Saddle bag with repair kit
- Optional: Map holder on handlebar
Pedal Options
- Flat pedals
- Half-toe pedals (without straps)
What’s Not Included
- Helmet
- Optional: clipless/SPD pedals with shoes
- Optional: your own saddle
- All accommodations
- All breakfasts
- 3 lunches
- 4 dinners
- Vineyard views galore!
- Unreal scenery: spin along the Sette Ponti Road
- Visit the land of the Etruscans
- Authentic Tuscan wine and olive oil tasting
- Visit quaint, non-touristy towns
- Ride to the Ponte Buriano, made famous by Leonardo da Vinci‘s Mona Lisa
2025
Start Location
San Giustino ValdarnoFly Into
Florence Airpoirt (FLR)End Location
CortonaFly Out Of
Florence Airpoirt (FLR)San Giustino Valdarno Warm-up ride
Meals Provided
Lunch, DinnerAverage Mileage
7 / 15 milesElevation Gain
455 / 1,491 ftRiding Terrain
Flat and gently rolling with a climb in the extra loopMeals Provided
Lunch, DinnerAccommodations
Villa Cassia di Baccano
Villa Cassia di Baccano is a Tuscany Resort in Italy, near Florence, Arezzo, and Siena, with a fascinating history. Built in the XVII century as a nun’s convent, a Roman noble family, the Cornacchia Palmieri, bought it and made it their Tuscany Villa after WWI. The property has a beautiful garden and swimming pool.
Loop to Reggello
Meals Provided
Breakfast, Lunch, DinnerAverage Mileage
38 / 42 milesElevation Gain
2,571 / 2,910 ftRiding Terrain
Easy rolling hillsMeals Provided
Breakfast, Lunch, DinnerAccommodations
Villa Cassia di Baccano
Villa Cassia di Baccano is a Tuscany Resort in Italy, near Florence, Arezzo, and Siena, with a fascinating history. Built in the XVII century as a nun’s convent, a Roman noble family, the Cornacchia Palmieri, bought it and made it their Tuscany Villa after WWI. The property has a beautiful garden and swimming pool.
San Giustino Valdarno To Arezzo
Meals Provided
BreakfastAverage Mileage
20 / 23 milesElevation Gain
925 / 1,174 ftRiding Terrain
Easy rolling hills, mostly gently descendingMeals Provided
BreakfastAccommodations
Vogue Hotel Arezzo
Located in the city’s heart, 4-star Hotel Vogue’s high-impact design and service dedication create a unique experience. The hotel offers exceptional rooms, each with a unique style and layout.
Arezzo to Cortona
Meals Provided
Breakfast, Lunch, DinnerAverage Mileage
40 / 46 milesElevation Gain
1,881 / 2,644 ftRiding Terrain
Flat and easy, rolling with three climbs; extra loop to Eremo delle CelleMeals Provided
Breakfast, Lunch, DinnerAccommodations
Villa Marsili
Villa Marsili in beautiful Cortona dates back to the late 700s, and the present owners have restored all original details and architectural characteristics lost in past centuries. The bedrooms, aimed to combine comfort and elegance, are spacious, bright, furnished with taste, and overlook the valley.
Loop to Castiglione del Lago
Meals Provided
Breakfast, DinnerAverage Mileage
25 / 42 milesElevation Gain
1,123 / 2,255 ftRiding Terrain
Rolling and flat, one climb to Cortona (extra loop)Meals Provided
Breakfast, DinnerAccommodations
Villa Marsili
Villa Marsili in beautiful Cortona dates back to the late 700s, and the present owners have restored all original details and architectural characteristics lost in past centuries. The bedrooms, aimed to combine comfort and elegance, are spacious, bright, furnished with taste, and overlook the valley.