A classic ride through the Tuscan hills...

Category 1 Riding Level (Least Difficult)

Price: $2,249 6 days/5 nights

$2,549 at 7 days/6 nights

(guided with vehicle support)

Average daily ride: 50km/30 miles

*extended routes available

Terrain: rolling hills with some extended climbing     

Click here for departure dates!

*available from April through October


  • Welcome lunch of Tuscan delights 
  • See the historic centers of Montalcino, Montepulciano, Pienza, & Cortona
  • Private visit and guided tasting of Vino Nobile at a small family operated winery in Montepulciano with the wine-maker/owner
  • Private visit and guided tasting of Brunello at an organic family operated winery in Montalcino with the wine-maker/owner
  • Private visit and tasting at a family operated organic farm and cheese maker with the owner
  • Cooking class and multi-course Tuscan dinner


Day One 


We meet in Cortona where you will be greeted by your group leader. After a light welcome lunch the leader will outline your map and give you detailed information regarding our daily rides and what we have planned for the week. Gear up for a warm-up ride now and get a little taste of what to expect before we really begin tomorrow. Tonight we will have a four-course dinner in the historical center of Cortona at a small and intimate Osteria


Day Two

Cortona – Montepulciano

Leaving Cortona behind we ride through the early morning mist in one of the largest valleys of Tuscany saving our legs for the ascent into Montepulciano. In the right season we will pass through fields of tobacco, sunflowers, durum wheat, and apples. Welcome to the bella Toscana! As we approach the hill town of Montepulciano, the landscape changes drastically. The valleys grow into hills covered in vineyards that create the delicious and highly sought afterVino Nobile, or wine of the Nobles. We visit a very special local winery followed by a guided tasting today, We will end the day with a robust dinner in the historic center of Montepulciano.


Day Three 

Montepulciano – Pienza – Montepulciano

Today we enjoy timeless landscapes of the Val d’Orcia, an area seemingly untouched by the modern world. We pass fields of grazing sheep riding to a local farm that produces Pecorino di Pienza, or sheep's milk cheese. After a visit of the farm, we enjoy a tasting of this delightful sheep’s milk cheese accompanied by fresh pears, fig preserves, and local honey. From here we ride to Pienza just in time for a light lunch and a stroll through town. Considered to be one of the most beautiful villages in Tuscany, Pienza is a perfectly preserved example of Renaissance architecture. From here we return to Montepulciano where we relax before your free night to enjoy dinner on your own. Your group leader will make arrangements for you.


Day Four

Montepulciano - San Quirico d’ Orcia

Today we really get off the beaten path when we discover some lonesome roads that take us through lush farmlands. The ancient cypress lined roads and views are breathtaking as we approach Radicofani and later on Bagno Vignoni, the famous medicinal hot springs. Used by the ancient Romans and as a retreat from Florence for the powerful Medici family, the springs are still functioning and are a perfect way to end a day of riding. Massage anyone? Let us know and we can make a booking for you. Post-ride we will dine in the agriturismo tonight with a typical multi-course dinner and wines sourced locally from the Val d’Orcia. 


Day Five 

San Quirico d’Orcia - Montalcino - San Quirico d’Orcia 

We have our most challenging hill of the week today. We will ride the lovely rolling hills with our destination looming ahead in the distance. On the ascent you will see Montalcino in the distance, a nearly impregnable defensive stronghold during the Middle Ages. Vino Brunello, an elegant and long lived wine that many consider to be one of the best in the world is locally grown and produced here. We will visit a local winemaker followed by a tasting to see just what these mighty grapes can achieve after a lengthy aging. The rolling road moves us back through the vineyards presenting stunning views of classic Tuscan countryside the entire way. We have a very special farewell dinner tonight featuring dishes prepared by you during our hands-on Tuscan cooking course.


Day Six 

San Quirico - Siena

Ride by the Abbey of Monte Oliveto Maggiore today, founded in 1445 by Olivetan monks, who transformed the hills into terraced farmland over the centuries. With luck we will arrive in time to catch part of the vespers service and chanting of the monks. Later on arrive in Asciano, a walled village located in this area known as Le Crete. It's a unique and almost lunar like landscape created by years of erosion on the clay based soil and just one of the many unique faces of the Tuscan landscape. Post ride, your group leader will guide you safely to the train station or your selected accommodation in the area.