Bicycling The Boot is a must-make trip at least once in a lifetime, but we offer tours in two diverse regions of Italy, because we’ve learned that one trip isn’t enough. Experience La Dolce Vita as you cycle past vineyards, through charming towns and along the sea, soaking in centuries of history and culture.

Our week-long tours — in storied Tuscany and Puglia, a favourite vacation spot for Italians and an emerging destination for foreigners — provide cyclists of all abilities with challenges and rewards in the form of stunning views, and yes, incredible food and drink.

Italy is a country bursting with heritage, be it cultural, culinary or architectural, which is why variety is a priority on our cycle tours in this remarkable destination.

Daily rides range from 20 to 70 kilometres as you cycle through olive groves and vineyards, along coastal roads and past walled villages. You’ll stop at cheese factories and hilltop monasteries, indulge in wine tastings and tour seaside caves, all the while meeting locals who are keen to share their stories with us. And we promise there will also be plenty of time for relaxing in the courtyard or poolside at the villas and B&Bs that you’ll call home.

Whether this is your first time to Italy, or one visit of many, we promise you’ll end the week with a new perspective on this beautiful country.

Italy bicycle tour map

Tuscany by bicycle


The town of Pienza, known as the “touchstone of Renaissance urbanism,” is our base for the couple of days of this trip, during which you'll enjoy bicycling on countryside routes to towns like Radicofani, home to one of the region’s most impressive medieval fortresses. You'll make your way northwest during the rest of the week, visiting abbeys, castles, and more vineyards before ending the trip in near San Gimignano. This tour is has some challenging hills, so it is recommended that cyclists have a moderate fitness level. Rides range from 10 to 70 kilometres, and have van support. Electric bicycles are available on this tour. Read more about this eight-day itinerary here including 2019 scheduled departures and prices.

Puglia by bicycle


An up-and-coming region in Italy, Puglia — the heel of Italy’s boot — will take your breath away, and at times, you’ll feel that you have the entire place to yourself. We start the week with a visit to Alberobello, a UNESCO World Heritage site famous for limestone huts with cone-shaped roofs that are unique to this region. After visiting Alberobello, our coastal rides throughout the week will take you through Ostuni, a town with prehistoric foundations, the buzzing port town of Otranto, and Lecce, dubbed the Florence of southern Italy, where you’ll have a guided tour. This tour has van support. Rides, which range from 30 to 65 kilometres, are suitable for all levels, though there are a couple challenging climbs. Electric bicycles are available. Read more about this seven-day itinerary here including 2019 scheduled departures and prices.

Our bikes in Italy


Kalkhoff e-bike

E-Bike - Kalkhoff

- Model: Agattu Impulse 8R HS

- Top notch drive

- 2.0 motor with sift-sensor

205 km range

- Tire size: 700 X 35 




Trek road bike

Road Bike - Trek

- Model: Emonda S 6

- Ultralight carbon frame

- Shimano / Ultegra components

- 22 speed (compact drivetrain) 

- Tire size: 700 X 23 or 25





Trek hybrid bike

Hybrid Bike - Trek

- Model: 7.3 fx

- Aluminum frame

- Shimano components

-27 speed

- Tire size: 700 X 32


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Also See:  Croatia | Ireland | Nova Scotia | Prince Edward Island | Newfoundland 

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