Assaggio Toscana

*$400 offer good on new reservations only while spaces last and not combinable with any other offers.

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.

Day 1 – San Donato
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 Ponte (Roman Road of Seven Bridges). You’ll be rewarded with a sample of homemade gelato in Regello.

Day 2 – Loro Ciuffenna
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 – Cortona
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 – Umbria
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. We'll provide a shuttle to Cortona's train station after breakfast. Why not extend your journey with a few extra days to see Florence's Renaissance treasures? We are happy to assist you with all your travel plans.