2025 classic TUSCANY fall tour

Itinerary

Day One: Welcome to Tuscany and Cortona / Welcome Dinner
Following your arrival at the Cortona Train Station, we will transfer you to this iconic medieval town that was featured in the two films “Under the Tuscan Sun” and “Life is Beautiful.” Following check-in for the next two nights in our four-star hotel, build up your bike or finalize the adjustments on your rental bike before enjoying a short spin to loosen up or explore the cobblestoned streets that feature stunning views over the Tuscan landscape. This evening, we’ll have our “Welcome Meeting / Dinner” at the hotel.

Day Two: Castiglion del Lago Loop / Wine Tasting
Begin your day with breakfast overlooking the Tuscan hills before riding to the village of Castiglion del Lago, nestled above Trasimeno Lake. Explore the village's castle and historic center before sampling the "tagliere con formaggi e salumi" or the traditional "pici" pasta for lunch. Afterwards, cycle through the rolling countryside to the Baldetti Winery for a reserved tasting of wines, bruschetta, olive oil, and pecorino cheese. Conclude your day by riding back to Cortona or take the sag van. This evening. explore the local restaurants of Cortona for dinner on your own.

Day Three: Cortona to Pienza
After a full Tuscan breakfast, start your day with a thrilling descent from Cortona as you embark on a memorable day in the saddle that will take you to two of Tuscany’s most celebrated villages, Montepulciano and Pienza, while riding through some of its most iconic landscapes. Following your arrival into Pienza, check-in to our four-star hotel for two nights before savoring a glass of the famous Vino Nobile. Afterwards, explore the local “trattorias” in town for dinner before walking along the town’s balcony with it’s incredible views of the Val d’Orcia!

Day Four: Bagno Vignoni and Montalcino
Our route for today will feature two of Tuscany’s most iconic destinations, Bagno Vignoni and the hilltop village of Montalcino. Our first stop will be the Roman spa town of Bagno Vignoni with its healing waters that have soothed generations of people seeking relief from their aches and pains. Afterwards, we’ll continue to the stunning hilltop town of Montalcino where you will be rewarded with spectacular views that go on forever! Following your return to Pienza, sample some of the Brunello wine from Montalcino before enjoying dinner on your own.

Day Five: Pienza to Murlo / Group Dinner
Fuel up for a memorable day in the saddle as you discover the “Terra di Sienna” on gentling rolling hills as you make your way to the quaint village of Murlo. Following your arrival, check-in to “cycling heaven” at our three-star hotel that encompasses a small village. Relax with a dip in the pool before celebrating your day’s ride with a festive group dinner!


Day Six: Murlo to Siena / Farewell Dinner
We’ve saved the best for last! Following breakfast, you will ride on rolling hills lined with cypress trees, vineyards and stunning Tuscan villas before entering beautiful Siena and finishing in the famous Piazza del Campo! After celebrating the conclusion of your ride, check-in to our three-star hotel with it’s amazing views of the Tuscan hills before exploring town to your heart’s content. This evening, we’ll conclude your Tuscany adventure with our “Farewell Dinner” in town.

Day Seven: Transfers
Following breakfast, we will transfer you to the Siena Train Station. From here, you can get a train to Florence or Rome for your departure home. (Please note: If you like a private cab to the airport in either Florence or Rome, please let us know and we will organize it for you. The cost will be your expense).