Italy: Tuscany & Umbria Biking & E-Biking

Day 1

We meet in the heart of Tuscany in the town of Siena. In the 12th century, it was one of Italy’s most powerful city-states, but now the city inspires awe with its medieval architecture, huge central square (el Campo), and protective walls. After introductions among the group and to our bicycles, we begin our ride through rolling hills, forests, and farmlands – much of it along a ridgeline – on our way to the town of Buonconvento. Just outside the town you will face your toughest hill of the day but the reward is worth it: our amazing agriturismo, a real working farm and vineyard where we stay for the night. We arrive at our inn in time to relax in the pool or take pleasure in our 360-degree view of the surrounding hillsides before walking across the fields to the dining room, where they serve us a delightful meal made with ingredients grown and raised on the property.
Biking Distance: 26 or 41 KM

Day 2

Today we ride to Pienza, an amazing hilltop town with a view over the entire Val d’Orcia below, one of the most famed valleys of Tuscany. We cycle along back roads with views of quintessential Tuscan valleys and stop at an abbey, several small towns and a centuries-old monastery: the perfectly preserved red brick Sant’Anna in Camprena, where some of the beautiful scenes for the movie The English Patient were shot. Once settled in at our hotel, we enjoy a tasting of Tuscan wines and cheeses (although it is in the center of wine country, Pienza is more well-known for its fine Pecorino cheeses!) on the hotel patio before sitting down to an al fresco dinner looking out over the valley floor. Afterwards, you might choose to take an evening stroll on the fantastic rampart overlooking the valley.
Biking Distance: 27, 43, or 67 KM

Day 3

Our ride today will bring us to Montepulciano, a wine town famous for its Vino Nobile, a luscious red wine that you will try during this afternoon’s included wine tasting! As we wander through the town’s historic streets, our Italian guide will offer his knowledge about the role Montepulciano played in Tuscan history. Those wishing to cycle in the afternoon can choose one of two loops back through the countryside to Pienza. One option includes a stop at Bagno Vignoni, a natural hot springs/bath, before returning to our hotel. Both routes allow you to stop for a gelato at a shop in Monticchiello that offers the best view of any we’ve ever visited! This evening, we enjoy a guided nighttime walking tour of town before our dinner at a local trattoria and an optional Limoncello (the classic Italian after-dinner drink) at a local taverna.
Biking Distance: 27, 41, or 55 KM

DAY 4: This morning we’ll transfer by private bus from Tuscany to another part of Italy – Umbria. In the quaint town of Torgiano, one of the centers of the Umbrian wine industry, we’ll reconvene with our bicycles and pedal our way blissfully to our next destination. En route, we’ll find a few small towns to visit and in which to enjoy lunch. Wandering through the flat Umbrian Valley will feel like a cakewalk after riding the Tuscan hills. The biggest challenge of the day will come on our short uphill ride to the town of Spello, a typical Umbrian town located on the edge of Mount Subasio and looking over the Umbria Valley. This will try your legs but please your soul when you see the fantastic views you have earned. Our four-star hotel is “home” for two nights and a multi-course dinner is just a short walk down the beautiful cobblestoned streets of town. We recommend a bedtime gelato on the return stroll to the hotel.
Biking Distance: 29, 45, or 51 KM

Day 5

Today you’ll find out why we love to bike in Umbria! From our front steps, we’ll have an incredible, mostly-flat ride across a hillside through olive groves, to a family run olive oil mill where we’ll have a tasting and learn how different grades of olive oil are made. Bruschetta with fresh olive oil is amazing! From there, we cycle to the famous town of Assisi, known mostly for its famous son, Saint Francis of Assisi. Even with its masses of tourists, Assisi boasts much more than its storied history and is a perfect stop for lunch and a little exploring through its winding streets. After lunch, our route takes us to the charming walled town of Bevagna and then on to the Arnoldo Caprai Winery, where we have a chance to savor the Umbrian wines and compare them to their Tuscan counterparts. We shuttle (or ride) back to our hotel, where you can choose to relax or explore town.  Tonight’s dinner is on your own in the lovely town of Spello.
Biking Distance: 22, 34, or 56 KM

DAY 6

We depart Spello this morning and all ride, on one route or another, to our final destination of Spoleto, perhaps the most “real” town of any we visit on this trip. Those looking for a challenge can choose to take side trips to Montefalco (center of the famous Sagrantino wine) or Trevi. Whether you choose to take part in the optional afternoon hike to the colossal and original Roman aqueduct, unwind at the hotel, or shop for souvenirs, you will find Spoleto alive with energy! Tonight we celebrate our last night together by taking part in a private Italian cooking class in our hotel and then feasting on what we have prepared together. Nobody will go hungry tonight!
Biking Distance: 38, 47, or 64 KM

Day 7

After breakfast, several possible loop rides will take you out of town and into the rolling rural countryside. These are actually some of our favorite rides for the empty roads and beautiful scenery. Upon your return, there will be time for a shower and then a walk to the train station, where your luggage will be transferred and we will bid one another farewell.
Biking Distance: 17, 32, or 38 KM