Italy – Tuscany Etruscan Treasures Bike Tour

Your bike tour starts from your hotel in charming Cortona, an iconic Tuscan medieval town. You will know of Cortona from the very famous book and film “Under the Tuscan Sun” and “The life is Beautiful” (La Vita è Bella), directed by and starring Roberto Benigni. Cortona embraces you with its charm and warmth, as you explore the cobblestone streets lined with cute cafés and boutiques. Take a moment to look over the city walls and enjoy the stunning views below. At 5:00 PM, our local representative will meet you at your hotel for your welcome briefing and bike set up! This time is fixed and travel must be planned accordingly.

Meals: on own
Highlights: Cortona exploration
Overnight: Cortona

Today’s ride will take you to Castiglion del Lago, a lovely ancient village overlooking the sparkling Trasimeno Lake. You will ride a route that takes you to the town. Once there, we suggest visiting the castle and the historical center, where you can browse small boutiques and shops. This is also the perfect place for your lunch! Consider having a “tagliere con formaggi e salumi.” This is essentially a charcuterie board. Delicious! Many delicatessen shops serve this, along with a salad. Or, you may decide to try the famous “pici,” a thick, squiggly-shaped, homemade pasta that is well-known in this area. On the return, consider stopping at Baldetti Winery to visit the wine cellar. Here, it is possible to taste their various products: wine, bruschetta with olive oil, and pecorino cheese. (Must be booked in advance.) Cycling 12 km more, your ride takes you back to Cortona. When you get back to hotel, enjoy a glass of wine and reflect on a lovely day full of adventure and discovery!

Meals: breakfast
Distance: 62 km / 39 mi, +568m
Highlights: Trasimeno Lake, Castiglion del Lago castle visit
Overnight: Cortona

Today is a nice ride through Siena’s province; it starts with the downhill from Cortona and terminates with the climb to Pienza.
There are two ride options today. If you pick the shorter ride you’ll have less elevation gain, but you’ll miss the well-known medieval hilltop village of Montepulciano. For both rides, you’ll meet uphill in Torrita di Siena, a small village located 15km from Pienza. Pienza became a UNESCO World Heritage Site in 1996 due to its cultural significance in urban planning: an impressive central square with surrounding cathedrals and clock towers. One of the most distinctive products of Pienza is the Pecorino Toscano. Enjoy this savory and salty sheep’s cheese that can be eaten aged or fresh. The regions of Tuscany, Sardinia, and Lazio (Pecorino Romano) claim to have the best Pecorino globally, so you won’t want to miss having a taste!

Meals: breakfast
Short: 49 km / 31 mi, +533m
Long: 63 km / 40 mi, +933m
Highlights: scenic Montepulciano, Pienza exploration
Overnight: Pienza

Today you have a choice of loop rides with return to Pienza. The long route takes you to Montalcino, one of the most famous towns of Tuscany. Once here, you can see why this place is special and not only for the Brunello wine! You will cycle through charming villages and wonderful landscapes, along forests and some of the typical countrysides that make Tuscany so famous. Some sections of this route travel on some busier roads as this is the only way to connect small country roads without going to gravel strada bianca. Have a delicious lunch in Montalcino and spend some time exploring this small town. On the way back, the ride stops at Bagno Vignoni, a small medieval village famous since the Roman times for its thermal waters. You may like to take the time for a relaxing soak here. (See supplement spa package in Rates section.) There is also an option to visit is the Sant’Antimo Abbey, the former Benedictine abbey with history dating back to the 8th century. The shorter ride option includes Montepulciano and Monticchiello before returning to Pienza (hilly).

Another option is a cooking class near Pienza: Traditional Italian Farm to Table Cooking class. You will tour the local farm with our chef/guide and learn how produce and dairy are produced in the region. Using farm raised produce and ingredients, you will learn how to make traditional wood-fired pizza and breads. Be sure to come hungry! Once your creation is complete, you will be able to eat the delicious food you have prepared. Please inquire for rates and reservations (must be booked in advance.)

Meals: breakfast
Short – Bagno Vignoni: 30 km / 19 mi, +421m
Long – Montalcino: 82 km / 51 mi, +1500m
Highlights: Montalcino, Bagno Vignoni, Sant’Antimo Abbey, Montichiello
Overnight: Pienza

Along the way to Siena you’ll ride through the UNESCO-awarded hills of the province, a beautiful environment made up of soft hills in a rich gold and brown color, referred to as “sienna.” In Italian “Terra di Siena” means earth. This particular color is made by earth pigments containing iron and manganese oxide, and it takes its name from the area of of Siena where it was produced during the Renaissance. Your ride stops for the night at the tiny village of Murlo. Here, the lovely Mrs. Brigida will welcome you at her comfortable accommodation where cyclists are alway welcome. Dinner is included at your accommodation tonight!

Meals: breakfast & dinner
Distance: 64 km / 38 mi, +813m
Highlights: scenic Siena cycling, charming Murlo
Overnight: Murlo area

After a delicious breakfast, continue to Siena. This is your last day of cycling and there is much to explore in Siena, so be sure to take your time! Make your way to the famous Piazza del Campo, adorned with the beautiful Mangia Tower. This piazza is the gathering place for Siena, and it is also the site for the well-known Palio horse race that takes place twice a year: once in July and once in August. Siena has several beautiful churches to visit, including the Siena Cathedral, a Romanesque-Gothic Duomo built in the 12th and 13th Century. As you explore this beautiful town, there are plenty of small boutiques and cafes to visit and enjoy.

Meals: breakfast
Distance: 29 km / 17 mi, +556km
Highlights: Piazza del Campo, Mangia Tower, Siena exploration
Overnight: Siena

Departure Day – unfortunately, your amazing Tuscan cycling adventure has to end but your time in Italy can continue! If you have time, we can help arrange a stop in Florence, Rome or other onward travels. Trains from Siena to Florence are possible. Take your time and enjoy your last morning in Siena before checking out.

Meals: breakfast