Italy | Tuscany | Iconic rolling hills, Medieval towns, Vineyards, Olive Groves & Cheese | ebike cycling Tour

After arrival at Florence Airport our team will transfer you to a beautiful country estate which will be our Tuscan hideout for the whole week. After welcome drinks, a tour overview and briefing await, where your tour leaders will fill you in on all the details of the Tuscany Cycling Tour. It’s best to get to know each other over a welcome dinner of local cuisine and wine produced locally. Your taste buds will be on high alert for the following week!

Meals: dinner
Accommodation: Il Casale Del Cotone or similar
Distance: 0 km (0 mi)

Start of your Tuscany Cycling Tour!

The biggest small city of Tuscany and a synonym for Tuscan architecture is today’s destination, the graceful Siena. Siena was one of the most important cities in medieval Europe and its historic center is a UNESCO World Heritage Site. It is also famous for its cuisine, art, museum, medieval cityscape, and the Palio, a horse race held twice a year in Piazza del Campo square. The route will take us over typical Tuscan rolling hills countryside, dotted with green vineyards and with views of colorful medieval towns like Monteriggioni.

Meals: breakfast, lunch, dinner
Accommodation: Il Casale Del Cotone or similar
Distance: 40 km (25 mi) / elevation 600 m (2000 ft) – return by shuttle

After getting accustomed to your bikes the day before, we have a long but marvelous riding day ahead of us. Riding the Strade Bianche (white gravel roads) we will be a part of the picture postcard scenery, riding between the vineyards and olive orchards. Don’t let the many hills ahead of us give you a fright, since e-bikes can make them flat or challenging, depending on your assistance setting.
Today’s highlight is the small town of Volterra, one of the most popular and visited medieval towns of Tuscany. A place of long history, since its being continuously inhabited for almost 3000 years.

Meals: breakfast, tastings / lunch, dinner
Accommodation: Il Casale Del Cotone or similar
Distance: 65 km (40 mi) / elevation 1600 m (5200 ft) – loop

Tuscany is more than just medieval history and dazzling countryside. For some, its main allure is its cuisine, and more importantly wine. The wine center of Tuscany is situated in the hilly region of Chianti which is the home of the red wine of the same name. Our visit to the Chianti region won’t be complete without tasting its exquisite top-quality wine
Today’s route winds between numerous vineyards and wine-tasting rooms, where we’ll try to whisk and sip a few authentic wines and other delicacies.

Meals: breakfast, lunch, dinner
Accommodation: Il Casale Del Cotone or similar
Distance: 40 km (25 mi) / elevation 900 m (3000 ft) – return by shuttle

To reach the southern part of Tuscany, we’ll employ our shuttle and get straight to the point. Less visited, but still authentic and tranquil villages of Montepulciano and Cortona will delight you with their charm. Montepulciano, the route start, is a Renaissance hilltop town, the center of the wine-producing region of the wine of the same name. The route will also take us along the shores of the largest lake in Tuscany and the fourth largest in Italy, Lake Trasimeno.

Meals: breakfast, lunch, dinner
Accommodation: Il Casale Del Cotone or similar
Distance: 60 km (37 mi) / elevation 600 m (1900 ft) – there and back by shuttle

Experience the Mediterranean Elba Island on two wheels. The island of Elba is the largest in the Tuscan Archipelago and a popular holiday destination for cyclists. It was a famous banquet place for Napoleon Bonaparte and it’s also home to one of the UNESCO World Heritage Sites, Portoferraio Fortress.
The shuttle will bring us to the port in Piombino, where we will embark on an hour-long ferry crossing. What awaits us on Elba is the spectacularly charismatic Portoferraio town, views of turquoise Mediterranean beaches, and a relaxing route over the ridge of the island with 360 degrees stunning views.

Meals: breakfast, lunch, dinner
Accommodation: Il Casale Del Cotone or similar
Distance: 40 km (25 mi) / elevation 1100 m (3600 ft)

A seemingly easy day will be full of cultural delights, photo stops, and fine architecture as we’re heading to the Renaissance world capital, Florence. To give you a head start, the shuttle will take us to the Chianti region from where we’ll descend slowly to the city of Florence and cross probably the most famous bridge in Italy, Ponte Vecchio (The Old Bridge).
Florence was the center of medieval European trade and finance and one of the wealthiest cities of that era, putting Florence in a position of enormous influence in Italy, Europe, and beyond. Florence City Centre is a UNESCO World Heritage Site full of spectacular basilicas, churches, monuments, and art galleries, such as the iconic basilica of Santa Maria Novella, Uffizi and Accademia museums, and the peculiar Fontana del Porcellino.
Our final group dinner will take place in the crown jewel of the Tuscan towns, our neighboring town of San Gimignano, a town of medieval towers, authentic ambiance, finger-licking meats, and artisanal gelato. Last day of cycling on your Tuscany Cycling Tour.

Meals: breakfast, lunch, dinner
Accommodation: Il Casale Del Cotone or similar
Distance: 30 km (19 mi) / elevation 500 m (1600 ft)

Departure day from Florence Airport. We suggest extending your visit for a few days to give yourself a few days of well-earned rest and to explore southern parts of Tuscany, or if you’re longing for more culture and gastronomic pleasures, dive into cities of Bologna, Modena, and Pisa at your own pace.

Meals: breakfast
Distance: 0 km (0 mi)