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Benvenuto! with true Italian panache, someone in dark sunglasses driving a Mercedes will whisk you out of the airport into the chaos of highway driving. When you open your eyes you will be in the oasis of calm known as Villa Armena. We’ll have some local specialities provided by Edoardo and Elena the owners before our afternoon spin to get loose. The aromas from Nicola Saporito’s kitchen will keep the most jet lagged awake for dinner tonight!

Ride distance: 25 miles Overnight: Buonconvento/Villa Armena

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The glorious Crete Senesi brings a magical sunrise followed by a kaleidoscope of fall colors on our ride up, over, through and down the vineyards that comprise the Brunello growing region. We’ll stop at a few of our favorite local artisans as we journey through the villages of Monteroni, Asciano, Montalcino and San’Antonio. We’ll have a private tasting as a preferred vineyard before exploring Montalcino for dinner on our own.

Ride distance: 45-65 miles Overnight: Buonconvento/Villa Armena

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The roads of Siena are known for the strade bianche, the white gravel roads that are legendary in the world of cycling. Today we’ll tackle them with gusto, channeling visions and strength of the great Tuscan cyclists- Bartali, Magni, Cipollini, Bettini, Tafi and Ballerini. Vintage bike is optional, but fortitude is mandatory as we journey into the history books of Italian cycling and culture. Tonight we embrace the past with dinner in the medieval center of Siena.

Ride distance: 45 or 75 miles Overnight: Buonconvento/Villa Armena

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Our point to point day links two distinct neighboring regions of Pisa and Siena. Along with the scenery, the food changes as do the wines. We’ll enjoy it all as we embrace our Pisano hosts at Relais Sant’elena, a reclusive hideaway in the hills above the Mediterranean. Dinner with Chef Deborah Corsa will show you a side of Tuscan food you never dreamed of!

Ride distance: 80 miles Overnight: Bibbona/Relais Sant’Elena

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Two time World Champion Paolo Bettini was raised in the village of Riparbella, just north of Bibbona and trained in the hills surrounding the medieval town of Volterra, our destination and known for its exquisite alabaster crafts. We’ll finish the day with a tasting of some Super Tuscans from a small winery before dinner with Chef Luciano Zazzeri.

Ride distance: 60 miles. Overnight: Bibbona/Relais Sant’Elena

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The Coppa degli Etruschi was an early season weekend series of professional races as riders prepared for the Spring Classics.  The Gran Fondo Etruschi honors these races annually and we’ll ride the course, which offers two different distances.

Ride distance: 55 or 85 miles Overnight: Bibbona/Relais Sant’Elena

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Our final day traverses the mountains and plains as we head inland to the southern tip of Florence, finishing at the Gino Bartali Museum to pay homage to Tuscany’s most famous cycling son.  We’ll venture into the city tonight and the San Frediano neighborhood for dinner with our good friend Matteo Fantini, who’s restaurant is reinventing locally sourced Tuscan cuisine.

Ride distance: 75 miles. Overnight: Bagno a Ripoli/Hotel Il Mulino di Firenze

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Grazie e Arrivederci! From the wines and roads of Siena, the strade bianche and l’Eroica to the coast, “la cucina del mare”, the medieval villages of Volterra, Castagneto and Suvereto, and the Super Tuscans of Bolgheri, it is our hope we’ve shown you a side of Tuscany you didn’t know existed. There’s plenty more of Italy to discover! We’ll get you where you need to be to begin your journey home today.