A tasting of Italy's most beautiful regions by bicycle.


Category 2 riding level (medium Difficulty)

Price: $2,249 6 days/5 nights                                       $2,549 7 days/6 nights                                       (GUIDED WITH VEHICLE SUPPORT)     

Average daily ride: 60km/37 miles

Terrain: rolling hills with some extended climbing and long descents

Click here for departure dates!

*available from April through October


  • Private visit and wine tasting of Sovana DOC and Super Tuscan wines with the winemaker at an organic winery in Maremma
  • Exploring the one-of-a kind and mysterious villages Cività di Bagnoregio, Pitigliano and Sorano
  • Bathing in the style of ancient Romans at the natural hot springs of Saturnia
  • Cycling up and over the extinct volcano of Monte Amiata into the beautiful Orcia river valley, a UNESCO world heritage site 
  • Private visit and unique tasting of Brunello at a highly rated family-run winery in Montalcino
  • Epic daily rides plus amazing food in a lesser known parts of Umbria, Lazio, and Tuscany
  • Organic farm accommodations, wineries, and meals


Day One

Orvieto - Civita di Bagnoregio - orvieto

We meet in Orvieto, an ancient Umbrian city found along the road between Rome and Florence and some even say halfway between heaven and earth. Built upon a high cliff of exposed compressed volcanic rock Orvieto is a sight to behold. Not to be missed however is the other “city” that lies beneath the silent darkness of the cliff which consists of a labyrinth of caves and tunnels carved over a three thousand year history. We suggest you arrive early to have more time to explore the city. We are guests this night at a nearby family-run organic agriturismo. Take a swim in the pool if the season is right and enjoy the superior view of Orvieto from the extensive gardens. There will be more stunning views of Orvieto on a loop ride in the hills around the city and in the neighboring region of Lazio to visit the one-of-a-kind village of Cività di Bagnoregio. Tonight we eat a multi-course dinner of locally sourced Umbrian specialties prepared with love by our hosts under a pergola of grape vines at our agriturismo.  


Day Two

Orvieto - Sorano

This morning we climb our way over the vineyard rich border of Umbria and into the lesser known but equally beautiful northern area of the neighboring region of Lazio. Marvel at the beautiful views of the valley below as we ride into the surrounding hills passing by castles and inviting villages along the way. Stop for a gelato or to have a closer look at the castle in tiny Torre Alfina and maybe grab a bite and admire the architecture in the small town of Acquapendente before we officially cross into Tuscany on our way to the ancient Etruscan stronghold of Sorano. Post-ride we will visit the medieval fortress of Sorano and the passageways below it. These next two nights we are guests at a small family-run eco-friendly agriturismo housed in a historic stone building. We dine here tonight on products sourced exclusively in the vicinity.   


Day Three

Sorano - Pitigliano - Sorano

Today we follow in the footsteps of the ancient Etruscans as we ride a fun yet challenging loop through Southern Tuscany or the area known as the Maremma. We pass through the striking villages of Sovana and then onto Pitigliano around lunch time. One of the three “Tufo cities”, Pitigliano was founded by the Etruscans and the area features many tombs and mysterious roadways built by this ancient and once powerful civilization. Take some time to stroll through it’s winding cobblestone streets and window shop the many local artisan’s wares. This evening, post ride, we will visit a small family-run organic winery, where will enjoy a private tour of the ancient Etruscan carved wine cellar followed by an ample wine and cheese tasting led by the owner and wine-maker of the estate. Tonight we dine in a local eatery nearby.


Day Four

Sorano - Saturnia

Today is a another scenic ride through rolling hills en-route to the thermally active area of Saturnia. We will have the opportunity to visit Sovana along the way and then we will rendevoux for lunch in the picturesque village of Montemerano located high above the surrounding area in the Tuscan Appenine mountains. Our lodging tonight is another family operated organic agriturismo. Tonight is a free night to enjoy dinner on your own. Being a free night, our group leader will make arrangements for you to dine in the village piazza. After dinner we make time to visit “Le Cascate”, the natural sulphuric hot spring baths known to soothe and even cure certain ailments. The waterfall and shallow pools are best enjoyed at night under a clear sky full of stars.


Day Five

Saturnia - Montalcino

Today begins with a challenging but scenic ascent of extinct volcano Monte Amiata. Upon reaching the summit, coast through the lengthy ride down passing through quant villages and the Montecucco wine production zone as the Orcia river valley slowly opens up before you and changes the landscape drastically. From here you will ride through the lovely hamlet of Castelnuovo del Abate and by the ancient Sant Antimo Abbey. Time it right and stop to hear the Gregorian chanting by the monks. Our final destination is Montalcino a nearly impregnable defensive stronghold during the Middle Ages. Brunello, an elegant and long lived wine that many consider to be one of the best in Italy if not the world, is locally grown and produced here. We will visit an organic winery, enjoy a full tasting, and follow it up with a special farewell dinner.


Day Six

Montalcino - Siena

After a long ride through the scenic rolling hills of Tuscan wine country our route takes us through the unique landscape around the Abbey of Monte Oliveto di Maggiore. The serpentine and rolling road offers stunning views of breathtaking Tuscan countryside the entire way. We will pass through the village of Asciano en route located in the geologically unique zone of Le Crete. It's an almost lunar like landscape created by years of erosion on the soft clay based soil of the provincial Sienese countryside. Once considered the badlands, today it’s a cyclist dream. This is a ride definitely not to be missed! Post ride, your group leader will guide you to the train station in Siena or your selected accommodation in the area.


*Day 7 (if doing extended tour option)

Orvieto Classico Loop

If you choose to do the weeklong version of this tour, this day's route will actually take place on the second day of the tour. The rest of the tour will then follow the above mentioned schedule in order. This route is one of the most challenging of the week as it traverses four long climbs that will weave you and your bike through medieval hamlets and quiet backroads found in the vicinity of Orvieto. Hugging the border of Umbria and Lazio we will climb into the hills through the Nature Reserve of Rufeno before descending back into the superb wine producing vineyards of the Orvieto Classico denomination. A great route that is at it's best in September as the grapes are ripe and ready to harvest!