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A taste of the best of Tuscany (and a slice of Umbria)
- Discover Tuscan olive oil
- Vineyard views galore!
- Spin along the delightful Sette Ponti Road
- Visit the land of the Etruscans
- Authentic Tuscan wine tasting
Our six-day Assaggio tour of Tuscany is a delicious, entry-level sampling of the world’s most beloved region! Begin pedaling in the upper Val d’Arno, a series of terraced foothills that hug the river Arno. These graceful hills are a curious blend of microclimates and a fertile ground for vineyards, olive groves, and nut trees. Stream and rivers cut into the hillsides to form delightful, twisting roads. We’re cooled by breezes in stone villages and warmed by the famous Tuscan sun. We conclude our tour in the storybook medieval village of Cortona brought to life in the recent motion picture “Under the Tuscan Sun” starring Diane Lane.
$3,395 - $3,595
Rolling, some flatland, heavenly
Total Mileage: 147 Daily Average: 30
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Day 1–2: San Donato and Loro Ciuffenna
Day 1: Admire the stunning panorama and warm sunlight of Tuscany as you zigzag through the olive groves and past the stone villas that line the beautiful Sette Ponti (Roman Road of Seven Bridges).
Day 2: Winding through the sun-drenched Pratomagno range, pass through tiny towns on a picturesque road lined with fig trees, vegetable gardens and vineyards. We'll then stop to visit an olive oil press.
Day 3: Arezzo
Zip through olive groves on your way to the Renaissance gem Arezzo, home of the works of Piero della Francesca and heartwarming backdrop for the Oscar-winning film “La Vita e Bella” (Life Is Beautiful).
Day 4–5: Cortona and Lake Trasimeno, Umbria
Day 4: The flatlands of La Val Di Chiana ease our velo voyage to Cortona, an exquisite hilltown filled with Etruscan treasures. A late-afternoon walking tour of this architectural gem leads to Roman arches, Etruscan tombs and Renaissance palaces.
Day 5: Cross the border to the Green Heart of Italy—Umbria—and the blue waters of Lago Trasimeno, where Romans and elephants once roamed. This is a favorite route for local cyclists, so make sure to say "SALVE" (greetings)!
Day 6: Arrivederci!
Enjoy one final stroll around this medieval wonder before you wish a final arrivederci. Why not extend your journey with a few extra days to see Florence's Renaissance treasures?
Jeannette F. from New Haven, CT had this to say about Assaggio Toscana:Assaggio Toscana is poetry in motion for its beauty that can barely be expressed in words.
Scott R. from Grafton, MA had this to say about Assaggio Toscana:The van seemed to magically appear whenever it was needed.
Liz W. from Brookline, MA had this to say about Assaggio Toscana:The best vacation of my life!
Scott S., Hickory, NC had this to say about Assaggio Toscana:I would highly recommend Ciclismo Classico. The guides were excellent. We definitely felt that we got a taste of the real Italy.
Sarah F., Lookout Mountain, TN had this to say about Tuscan Fantasy:Meals and day trips were great and the pool was fantastico!
Bill M., San Jose, CA had this to say about Assaggio Toscana:As with a first taste of any fine wine, your Assaggio Toscana has whetted my appetite for much more of your beautiful country. I'll cherish the memories of our dinners at the Fattoria, our climbs up those beautiful hills and most of all the small personal details along the way." Never has the word 'Classico' been more appropriate!
Lilly G., Northampton, MA had this to say about Assaggio Toscana:The complete sensory experience of cycling through Tuscany offered great insight into the passionate Italian temperament!
Bill M., San Jose, CA had this to say about Assaggio Toscana:Our meals were one of the highlights of the entire week.