There’s something almost poetic about exploring Italy by bicycle. Perhaps it’s the way the morning mist clings to Tuscan cypress trees as you climb yet another hill, or how the Ligurian Sea sparkles beyond each hairpin bend of the Cinque Terre.
In a country where life moves at a speed that entirely depends on when you had your last espresso, cycling offers a rhythm that feels just right – fast enough to cover ground, slow enough to absorb every detail.
And you can only, truly absorb every detail if your mind isn’t fixated on plotting your next move the whole damn time. We’re here to lighten the load, metaphorically speaking, and help you get ahead with the planning side of things, so you can luxuriate in that feeling of the open road properly, fully and without tedious distraction.
With that in mind, here are some suggested itineraries that piece together sections of Italy’s most beautiful roads, many immortalised in the country’s great cycling races. You’re in for one hell of a ride…
The Chianti Classic
Route: Florence to Siena loop (suggested itinerary)
Distance: Approximately 200 km
Duration: 3-5 days
IDEAL for: Intermediate cyclists who appreciate combining cultural visits with their riding. The route offers plenty of opportunities to stop at historic towns, vineyards, and local restaurants, making it perfect for those who view cycling as part of a broader Italian experience rather than purely about covering distance.
This suggested route through Tuscany’s undulating landscape incorporates sections of the famous Strade Bianche race, known as “Italy’s most beautiful race”. The white gravel roads that give the race its name create one of cycling’s most spectacular one-day events each March, when professional riders battle over the steep hills of Siena province. Our leisure-paced itinerary follows some of these iconic gravel sections while also taking in the classic Tuscan landscape between Florence and Siena.
The route can be customised to your preferences, but we suggest including the stretch through Gaiole in Chianti, where the famous L’Eroica vintage cycling event starts each October. This non-competitive celebration of cycling heritage attracts thousands of enthusiasts riding pre-1987 bikes along the historic white roads. It’s also massively popular with motorcyclists.
Insider Tip: The majority of cycling tours in Italy are timed for May or September, to avoid both the summer heat and crowds. The morning light in these months is particularly magical for cycling through the Tuscan countryside, and you’ll find many agriturismi (farm stays) more readily available for overnight stops.
The Dolomites Challenge
Route: Cortina d’Ampezzo Circuit (suggested itinerary incorporating famous Giro d’Italia climbs)
Distance: 85 km
Duration: 1-2 days
IDEAL for: Experienced cyclists and climbing enthusiasts who relish steep ascents and technical descents. This route is best suited to those with good fitness levels and experience in mountain riding.
This challenging circuit incorporates some of the most famous climbs in professional cycling. The Passo Giau (2236m), regularly featured in the Giro d’Italia, was the scene of Egan Bernal’s epic solo victory in the 2021 edition through the snow. The Passo Falzarego (2105m), another Giro favourite, has been crossed more than 40 times in the race’s history.
You can adapt this route to your abilities by choosing which passes to tackle – the classic combination of Giau and Falzarego makes for an unforgettable day, while adding the Passo Pordoi (2239m), known as the ‘Queen of the Dolomites’, creates an even more epic challenge. This pass has been crossed more times than any other in Giro history and hosts the Cima Coppi (highest point) of the race when included in the route.
Insider Tip: Start your ride no later than 7am to avoid afternoon thunderstorms, which are common in the Dolomites during summer months. Always carry a lightweight waterproof jacket and arm warmers, as temperatures can vary dramatically between valleys and mountain passes.
Sicily’s Coastal Circuit
Route: to Cefalù (suggested itinerary incorporating Giro di Sicilia routes)
Distance: 250 km
Duration: 4-6 days
IDEAL for: Cyclists who enjoy mixing terrain and cultural experiences. The route offers a perfect blend of coastal cruising and mountain challenges, with plenty of opportunities to explore Sicily’s rich archaeological heritage and distinctive cuisine.
This suggested itinerary pieces together sections of the Giro di Sicilia race route, including parts of the dramatic coastal road that regularly features in this spring stage race. The route through the Madonie Mountains follows roads used in the 2023 edition, where Damiano Caruso thrilled local fans with a decisive attack on the final climb.
The beauty of this route is its flexibility – you can follow the flatter coastal sections for easier riding, or challenge yourself on the inland climbs that have tested professional riders in both the Giro di Sicilia and the Giro d’Italia’s Sicilian stages.
Insider Tip: The coastal roads can get busy with traffic, particularly in summer. Plan to tackle these sections early in the morning and save the quieter inland routes for later in the day. Local cyclists recommend carrying extra water during the summer months, as drinking fountains are less common than in northern Italy.
Read: Where to eat in Catania
The Prosecco Road
Route: Conegliano to Valdobbiadene (following sections of the Giro d’Italia time trial route)
Distance: 60 km
Duration: 1 day
IDEAL for: Wine enthusiasts and photographers who enjoy a challenging day ride. This route suits cyclists who appreciate a good climb followed by a rewarding glass of Italy’s finest sparkling wine.
This route follows parts of the spectacular 2020 Giro d’Italia time trial course, where Filippo Ganna powered to victory through the UNESCO-listed Prosecco vineyards. Known locally as the ‘Strada del Prosecco’, these roads have also featured in the Giro Rosa (now the Women’s Giro d’Italia), offering challenging climbing among some of Italy’s most prestigious wine estates.
Insider Tip: Book your vineyard visits in advance, as many require reservations. The best time to cycle this route is during the harvest season (late August to early October) when the vines are heavy with grapes and the whole region buzzes with activity.
The Great Lakes Tour
Route: Lake Como to Lake Garda (suggested itinerary incorporating Il Lombardia routes)
Distance: 180 km
Duration: 2-3 days
IDEAL for: Confident cyclists who enjoy varied terrain and dramatic scenery. Perfect for those who want to combine challenging riding with opportunities to explore historic lakeside villages and elegant villas.
This suggested route connects two of Italy’s most famous lakes via roads that have witnessed some of cycling’s greatest moments. The section around Lake Como incorporates parts of Il Lombardia’s finale, including the famous Madonna del Ghisallo climb – a chapel at its summit serves as cycling’s spiritual home and houses a fascinating museum of cycling history. The route to Lake Garda can be customised to include varying degrees of challenge, from the gentle lakeside roads to more testing climbs in the pre-Alpine foothills.
Insider Tip: The roads around Lake Como can get extremely busy, especially on weekends. Plan your departure from Como for early Sunday morning when traffic is at its lightest, and consider taking the ferry across some sections of the lakes to avoid the busiest stretches of road.
The Bottom Line
While these suggested routes piece together some of Italy’s most beautiful cycling roads, they should be viewed as starting points for planning your own adventure. The joy of cycling in Italy lies in the flexibility to adapt your route based on your interests and ability – whether that means tackling the same legendary climbs as your cycling heroes or meandering through quiet backroads in search of the perfect gelato stop.
The key is to allow enough time to appreciate not just the cycling, but the rich tapestry of Italian experiences that make riding in the country so special.