🇮🇹8days/7nights | 🍷🍺 Wine/Beer | 🚵🏽‍♀️ ~60km per day | ⇵ Advanced | €3500 pp - Dbl Occupancy

Tour description

There is something deeply satisfying about crossing a country by bicycle. Watching the landscape change one pedal stroke at a time. Climbing into the mountains under your own power. Rolling into medieval towns as church bells echo through ancient streets. Ending each day around a table filled with regional food, local wine, and stories from the road.

Our Tuscany to the Adriatic tour is designed for cyclists who value unforgettable riding as much as authentic travel.

Beginning in the coastal town of Piombino, the route leaves the Mediterranean behind and winds through the quiet backroads of Tuscany, where vineyards, cypress-lined lanes and hilltop villages create some of Italy's most iconic scenery. Your first destination is the medieval village of Castelnuovo di Val di Cecina, a hidden corner of Tuscany that rewards riders with peaceful roads and spectacular views.

From there, the journey continues to Siena, one of Italy's most beautiful medieval cities. Rather than rushing through, we've built in a full rest day so you can experience the city at its own pace. Wander the Piazza del Campo, admire the magnificent Duomo, sip an espresso in a quiet piazza, or simply enjoy the luxury of an afternoon with nowhere to be but Italy.

The second half of the adventure reveals a different side of the country. Leaving Tuscany, the roads become wilder as we ride towards San Giustino Valdarno and into the foothills of the Apennines. Long climbs are balanced by exhilarating descents, quiet mountain roads and the kind of scenery that reminds you why Italy remains one of the world's great cycling destinations.

The ride to Pieve Santo Stefano offers some of the week's most rewarding kilometres before the route climbs once more towards the remarkable Republic of San Marino. Rising dramatically above the surrounding countryside, its stone towers and panoramic views provide a fitting final mountain destination before the descent to the Adriatic.

Our journey concludes in Rimini, where the sea welcomes you after eight unforgettable days in the saddle. Celebrate your achievement with a swim, an aperitivo on the waterfront, and one final evening with new friends who have shared every climb, descent and unforgettable moment along the way.

This is more than a bike tour. It is a carefully curated cycling holiday built around exceptional routes, locally owned accommodation, outstanding regional cuisine and the simple pleasure of discovering Italy at the perfect pace. We take care of the logistics, luggage and support so you can focus on what matters most—the ride.

Every great cycling holiday tells a story. This one begins on the Tyrrhenian Sea, crosses the hills and mountains of central Italy, and finishes with your front wheel touching the Adriatic—a journey measured not just in kilometers, but in unforgettable experiences.

Tour Highlights

• 8 days / 7 nights across the heart of Italy

• Ride from the Tuscan coast to the Adriatic Sea

• Explore the medieval cities of Siena and San Marino

• Rest day in Siena to experience one of Italy's great cultural treasures

• Quiet roads through Tuscany, the Val d'Orcia and the Apennines

• Boutique accommodation selected for comfort, character and hospitality

• Authentic regional food, local wines and unforgettable Italian hospitality

• Daily luggage transfers

• Carefully designed routes that balance challenge, scenery and enjoyment

• Small group, experienced guides and a relaxed, welcoming atmosphere