A bike tour with a little bit of everything.



Category 2 Riding Level (Medium Difficulty) 

Price: $2,249 usd 6 days/5 nights

(guided with vehicle support)

*this route can be extended by one day  

Average daily ride: 60+km/37+miles

Terrain: rolling hills with some extended climbing

Click here for departure dates!

best time to ride it?                                                   May, June, September, early October

*Available from April through October


  • Private tour of Volterra historic city center a UNESCO World Heritage site
  • Full multi-course Tuscan cooking class and dinner 
  • Private aperitivo and wine tasting at Moris Farms  
  • Private visit of an Organic Pecorino cheese farm
  • Epic daily rides plus the best food of the interior and seaside of Tuscany

Day One

Siena - Volterra

We meet you in Siena to begin this amazing tour of land and sea. Ride from the medieval walls to one of the highest and most ancient of the Tuscan hill towns. Beautiful Volterra awaits you, a magic and mysterious city with roots in three thousand years of history. Set upon a hill at 550 meters above sea-level, it has a striking view over the mountains and even to the distant sea on a clear day. The landscape of this zone is dramatic and rugged and makes for an unforgettable cycling experience. Post-ride we meet up again for a personal walking tour of the historic center of Volterra. Dinner tonight is in a local eatery in Volterra. 


Day Two

Volterra Loop via San Gimignano  

Ride deeper into breathtaking scenery around San Gimignano today while soaking in some sun and stopping for photos in the countless rows of vineyards. Take a break for an espresso or even lunch in San Gimignano followed by a stroll through the cobblestone alleyways. Post-ride have a dip in the pool before you cook your own dinner during our unique Tuscan cooking course featuring fresh handmade pasta, and other local specialties from the surrounding forest. 


Day Three

Volterra - Massa Marittima

Start the day with an informative visit of the cheese making facilities and find out what makes a good wheel of Pecorino. Gear up for a fun descent from the barren walled chasms of Volterra and into the Era Valley. Eventually the route leads us into the dense wilderness of Southern coastal Tuscany otherwise known as the Maremma. This inspiring, evocative landscape reveals a wealth of natural beauty, history, art, and architecture. The medieval fortresses, villages, and castles along the way endow the landscape with a timeless atmosphere. 


Day Four

Massa Marittima - Isola d’Elba

Ride the rest of the way to the port through the scenic forests and coastal plains where we will embark on an easy and scenic one hour ferry to Portoferraio on Elba Island. Take in the views while enjoying the mediterranean climate and clear blue water from the upper deck of the boat or have a snack during the crossing in the ships cafe. Back on land and back on the bikes, our base for the remaining nights is just a short ride away. We welcome you to Elba with a dinner al fresco under the pergola at our boutique hotel.  


Day Five

Isola d’ Elba Western Loop

Today you can bike or enjoy a day of absolutely nothing but complete relaxation on the beach, or maybe even both. The ride is an epic loop today where we will discover the almost untouched and pristine waters of the western coast and of Elba. Cliffside roads take us above the rocky and imposing coastline where the most adventerous will find some of the best and most natural beaches.  Tonight ends with a special farewell dinner.


Day Six

Isola d’Elba Eastern Loop - Piombino

Today we will enjoy one last outing with a vigorous early morning loop ride featuring bird’s eye views from the eastern side of the island. With this route completed you will have pedaled over most everything that Elba has to offer. We then get you back to the mainland via ferry by early afternoon, rested and relaxed. From the train station of Piombino you will easily find services to Pisa, Lucca, Florence and beyond.