Italy is a dream destination for cyclists, offering a tapestry of landscapes and rich culture. From the sun-drenched hills of Tuscany to the dramatic cliffs of the Amalfi Coast, Italy’s varied terrain caters to all types of cyclists. Whether you’re a seasoned road cyclist seeking the thrill of alpine ascents in the Dolomites or a leisure rider looking to savour the scenic countryside dotted with vineyards and olive groves, Italy has something for everyone.
Cycling in Italy immerses you in the local culture, cuisine, and natural beauty of the landscape you ride through. Each region offers its charm and challenges, ensuring every itinerary and holiday is unique. It’s not just the scenery and cycling that changes by region, experience different foods, wines and traditions in every area you visit. To explore some of the best cycling holidays in Italy, visit Skedaddle for expert-planned itineraries that will make your Italian cycling dream a reality. Join us as we delve into the best cycling routes and breathtaking places to pedal.
Puglia to Cilento – Coast to Coast
Highlights
- Explore less travelled regions
- Sections of flat riding and gentle hills
- Unique heritage
The Puglia to Cilento Coast to Coast is a captivating cycling journey through southern Italy’s lesser travelled yet most engaging regions. This popular route takes you from the sun-drenched olive groves of Puglia to the enigmatic panoramas of Basilicata and Calabria, showcasing the authentic ‘Mezzogiorno.’ Cyclists will be charmed by the Mediterranean culture, delicious local cuisine, and the warmth of the people. Starting in Puglia’s Monopoli, riders traverse flat terrains amidst vast olive groves and vibrant orchards. From here, they venture into Basilicata. Cycling through this magical region provides a glimpse into Italy’s deep history. As the route continues, the journey takes you through vast fields, unique rock formations, and the enchanting towns of Alberobello and Matera, a UNESCO World Heritage site known for its ancient stone dwellings. The ride culminates in the pristine surroundings of Cilento National Park, offering quiet roads, stunning coastal views, and a delicious taste of southern Italian life.
Our cycling holidays in Puglia
L’Adriatico al Tirreno – Italy’s Coast to Coast
Highlights:
- Two very different coastlines
- Picturesque rolling hills
- Stunning Renaissance architecture
Designed to combine some of Italy’s most stunning and interesting locations, every village and town this route visits showcases Renaissance architecture that has nothing to envy in Rome. Be amazed by the Duomo of Orvieto, Palazzo dei Consoli in Gubbio and the Basilica of San Francis in Assisi as you pedal from San Marino on the Adriatic coast to the Tyrrhenian Sea. Enjoy traversing varied landscapes, rolling hills, and medieval hilltop towns on this incredible route.
Starting in Riccione, a cycling haven in Emilia Romagna, explore its coastal roads before heading inland through the hills of Marche’s and the scenic Apennine Mountain passes. In Umbria, the “Green Heart of Italy” relish three days of riding amidst its forested countryside and medieval towns, savouring local cuisine. This stunning journey concludes in southwestern Tuscany, when the Tyrrhenian coast is reached, and the route crosses the Tombolo di Feniglia, the narrow stretch of land connecting mainland Italy to the Argentario peninsula.
Our cycling holidays – L’Adriatico al Tirreno
Strade Bianche
Highlights:
- Ride in the wheel tracks of pro-racers
- Adventure and challenge
- Classic Tuscan scenery
Uniquely found in Tuscany, the Strade Bianche translates to ‘White Roads’, these sinuous ribbons of white gravel and chalky limestone provide a unique texture and challenge for cyclists and give their name to the professional UCI World Tour race, Strade Bianche. The Strade Bianche pro-race is a great favourite amongst riders and fans, its challenging parcours rivalling the classic cobbled races of France and Belgium but with the beauty of the Tuscan landscape adding to the drama of the race. Appreciated by road racing fans, gravel riders and leisure cyclists, these iconic white roads are nature’s gift to cyclists, attracting riders from all around the world to experience Tuscany’s captivating views and famed cycling heritage.
Our cycling holidays on the Strade Bianche
- Strade Bianche Explorer – Guided Gravel Holiday
- Strade Bianche Explorer – Self-Guided Gravel Holiday
La Via Claudia
Highlights:
- Follow ancient Roman roads
- Savour relaxed riding
- Discover more history, food and culture
The Via Claudia Augusta, a 2,000-year-old Roman-built road, historically served as the main commercial route across the Alps, facilitating the transport of goods like wine from Spain, Mediterranean oysters, and even Asian spices. Today, it offers an unparalleled cycling experience through picturesque countryside and historical sites, stretching from the Po River lowlands and the Adriatic Sea to Bavaria and the Danube. This ancient path has undergone a renaissance, symbolising the union of cultures and the harmony of Europe with its varied terrains and traditions. The route spans three nations, each offering unique artistic treasures and culinary delights. As a cyclist, you’re invited to explore this path from a fresh perspective, immersing yourself in the colours, fragrances, and flavours that define the route’s history. Find out more about the highlights of the route from cyclist David Cartmell.
Our cycling holidays on La Via Claudia
Stelvio Pass
Highlights:
- Tick off a bucket-list climb
- Conquer the infamous hairpin bends
- Immerse yourself in spectacular mountain scenery
The Passo Stelvio is a legendary road celebrated for its dramatic natural beauty and vertigo-inducing curves. Located at 2,757 meters, it stands as Italy’s highest mountain pass, connecting Bormio in Lombardy with Prato in South Tyrol. The pass was constructed over five years, completed in 1825 under Emperor Franz I, and originally served to link Lombardy, then part of the Austrian Empire, with the rest of the empire. This iconic road spans nearly 50 km with 48 hairpin bends, offering vertiginous views of alpine greens, volcanic rock formations, and nearby glaciers. The Stelvio is not the highest pass in Europe, but its unique blend of challenging climbs and stunning panoramas attracts cyclists worldwide.
The two sides of the Stelvio offer distinct challenges: the east side, with its awe-inspiring views, features a gentler ascent, while the west side is known for its more demanding climb, iconic switchbacks, and rewarding sense of accomplishment. Cyclists can embark on a remarkable route starting with an ascent on the east side, crossing the Umbrail Pass into Switzerland, and tackling the rigorous climb from Prato allo Stelvio on the west. This 60-mile journey, involving around 10,000 feet of elevation gain, punctuates Stelvio’s reputation as an unparalleled cycling achievement, firmly rooted in its epic scale and grandeur. Cycling in the wheel tracks of the pro racers is no easy task so steel yourself for the Stelvio, it will be one of the hardest but most rewarding days you will have on your bike.
Our cycling holidays riding Stelvio
Cycling Holidays in the Dolomites
Italy End to End
Highlights:
- Cross Italy using only your pedal power
- Intimately learn the differences between the regions
- Immerse yourself in Italian culture
Cycling the Italian End to End is a captivating journey that offers much more than just a scenic ride; it’s a cultural odyssey through one of Europe’s most diverse and fascinating countries. Italy’s varied scenery and regional differences make this end-to-end journey particularly fascinating.
Starting in the north, cyclists are greeted by the lush, dramatic coastlines of the Cinque Terre, where vibrant villages cling to steep cliffs. This region shows the blend of maritime charm and rugged beauty, setting the tone for what’s to come. As the route ventures southward, cyclists travel through Tuscany’s rolling hills, renowned for Chianti vineyards and artistic heritage. Tuscany’s landscape, with its golden fields and cypress-lined roads, embodies the quintessential image of Italian beauty.
Approaching central Italy, the journey threads through Umbria, a land characterised by its medieval hilltop towns and serene landscapes. It’s a place where tradition and history are palpable, offering a glimpse into Italy’s ancient past. Riding through the lesser-known regions of Abruzzo and Molise unveils untamed natural parks and authentic Italian character, less influenced by tourism.
As cyclists enter the southern regions, they encounter significant cultural shifts. The south is a blend of Baroque architecture, olive groves, and sun-baked terra cotta landscapes. Regions like Puglia, with its iconic trulli, the traditional limestone dwellings unique to the area, renowned cuisines and warm hospitality offer a different experience from one you can have anywhere else.
Throughout the journey, cyclists experience Italy’s remarkable geographic diversity—from the high Apennine peaks to the flat, fertile plains. The contrast between Italy’s industrial north, with its cosmopolitan cities, and the more relaxed, rural southern regions highlights the country’s varied traditions and lifestyles. This diversity, combined with world-class cuisine, historical sites, and the welcoming spirit of its people, makes cycling the Italian End to End an adventure of a lifetime.
Our Italy End-to-End cycling holidays
- Grand Traverse Classic – North to South – Guided Road Cycling Holiday
- Grand Traverse Explorer – South to North – Guided Road Cycling Holiday
Sardinia Coast to Coast
Highlights:
- Relax in the welcome of Sardinian hospitality
- Get off the beaten track
- Enjoy the variety of riding one island offers
Cycling the glorious coastline of the island of Sardinia offers an enchanting experience filled with natural beauty and cultural richness. Known for its crystal-clear turquoise waters and pristine beaches, Sardinia’s coastline provides a picturesque backdrop for any cycling adventure. The island’s diverse terrain features gentle hills, rugged cliffs, and lush greenery, creating a dynamic and enjoyable ride for cyclists of all levels and across all cycling types – road, leisure, mountain bike or gravel bike.
As you pedal along the coast, each turn offers new vistas, from hidden coves to sweeping ocean views that captivate the senses. The journey into the wild heart of the island is interspersed with charming villages and historic towns where riders can indulge in Sardinian hospitality and culinary delights, such as fresh seafood, local cheeses, and the island’s renowned Cannonau wine made with a grape variety (known as Grenache in France) that is at its best in hot, dry climates.
In addition to its scenic beauty, Sardinia boasts an extensive network of cycling routes that allow cyclists to explore off-the-beaten-path locations, uncovering ancient ruins and cultural landmarks. Cycling in Sardinia offers a perfect blend of nature, culture, and adventure, providing an unforgettable Mediterranean cycling experience. Our Skedaddle team have been based on the island of Sardinia for 20 years – find out all their favourite things about cycling in this Mediterranean paradise.
Our cycling holidays in Sardinia
- Sardinia Coast to Coast – Guided Mountain Bike Holiday
- Sardinia Coast to Coast – Self-Guided Mountain Bike Holiday
- Sardinia Coast to Coast – Self-Guided Road Cycling Holiday
- Sardinia Coastal Explorer – Guided Road Cycling Holiday
- Sardinia Coastal Explorer – Self-Guided Road Cycling Holiday
- Sardinia Island Flavours – Self-Guided Leisure Cycling Holiday
- Sardinia Island Flavours – Guided Leisure Cycling Holiday
- Sardinia Island Traverse – Guided Electric Mountain Bike Holiday
- Sardinia Cape to Cape – Guided Gravel Riding Holiday
Salento Circular (Puglia)
Highlights:
- Relaxed riding through ancient olive groves
- Visit the vineyards and enjoy their produce
- Stunning coastal riding
Salento, in Puglia, is the southern heel of Italy, cycling here offers a captivating journey through one of Italy’s most celebrated regions. Some even say it is one of Italy’s best-kept secrets and a place discerning travellers should not miss! The Salento Circular Route provides cyclists with an unforgettable experience, weaving through stunning coastal landscapes, charming villages, and historic towns. Known for its turquoise waters, white sandy beaches, and dramatic cliffs, the coastline offers a scenic backdrop for cyclists looking to explore the region’s natural beauty.
As you ride, you’ll encounter the quintessential elements of Salento’s charm: ancient olive groves, vibrant vineyards, and Baroque architecture. The route invites cyclists to immerse themselves in Salento’s unique cultural blend, evident in its local traditions and delicious cuisine, featuring fresh seafood, homemade pasta, and verdant olive oil.
The circular route is accessible to cyclists of all levels, offering well-paved paths and gently rolling terrain that provides both relaxation and adventure. As you journey through Salento, you’ll discover a land where history and tradition meet sublime landscapes, creating a cycling paradise that embodies the essence of southern Italy. Discover why Tom and Gillian were charmed by their time at the “heel” of Italy.
Our cycling holidays in Puglia
- Puglia – self-guided leisure cycling holiday
- Puglia – guided leisure cycling holiday
- Puglia, The Beautiful South – self-guided road cycling holiday
Giro della Toscana
Highlights:
- Classic Tuscan cycling in rolling hills
- Explore the hidden streets of medieval towns
- Pedal through the famous wine regions
Cycling in Tuscany is an enchanting journey through one of Italy’s most iconic landscapes, filled with timeless beauty and vibrant villages. The region’s rolling hills, lined with cypress trees and dotted with medieval hilltop towns, create an evocative backdrop to the smooth rolling roads. Beginning the adventure in the charming medieval spa town of Casciana Terme, riders are welcomed with superb dining options and delightful gelaterias.
The route winds south through verdant olive groves to San Gimignano, known as the ‘town of towers’ for its impressive medieval skyline and well-preserved architecture. As cyclists continue, the paths lead into the Parco della Val d’Orcia, a UNESCO World Heritage site celebrated for its unique conical hills and expansive chalk plains. This region is also a haven for wine lovers, with opportunities to savour Brunello in Montalcino and Chianti Classico in its namesake area.
The journey culminates in the historic hilltop town of Volterra, known for its twin castles and ancient allure. The final day offers a return to Casciana Terme, where cyclists can unwind in the soothing thermal waters, reflecting on a journey that has blended Tuscany’s natural beauty with cultural and culinary delights. Find out what cyclists think of what is surely one of Italy’s best cycling routes.
Our roady cycling holidays in Tuscany
- Giro della Toscana – Guided Road Cycling Holiday
- Giro della Toscana – Self-Guided Road Cycling Holiday
Tour of Lombardy
Highlights:
- Best of lakes and mountain riding
- A region steeped in pro-racing history
- Awe-inspiring scenery
Cycling in Lombardy offers an unforgettable journey, capturing the thrill of diverse terrains alongside the stunning beauty of its famed lakes and taking inspiration from the prestigious Tour of Lombardy. Known as “The Race of the Falling Leaves,” this annual cycling monument marks the end of the European season every autumn, with routes alternating between the charming cities of Bergamo and Como. First raced in 1905, the Tour of Lombardy embodies the region’s cycling spirit and appeals to enthusiasts of all levels.
Lombardy’s lakes—Como, Maggiore, Garda, and Lugano—are mesmerising highlights of this cycling region. Each offers unique landscapes, from the magnificent vistas of Lake Como to the serene waters of Lake Maggiore. Lake Garda, with its diverse landscapes, and Lake Lugano, offering a blend of Italian-Swiss culture, complete the experience. Cycling in this region is a rewarding exploration of nature and history, as we discovered when we were stretching our legs in Lombardy.
Our cycling holidays in Lombardy
- Lakes of Lombardia – Guided Road Cycling Holiday
- Lake Garda to Venice – Self-Guided Leisure Cycling Holiday
- Lake Garda Explorer – Self-Guided Family Cycling Holiday
- Lake Garda to Venice – Self-Guided Family Cycling Holiday
Via Francigena – Tuscany to Rome
Highlights:
- Ride the ancient pilgrimage routes
- Explore deep into the countryside
- See the changing landscapes as you ride
The Via Francigena is an ancient pilgrimage route stretching from Canterbury to Rome, the Tuscan section, beginning in Siena and finishing in Rome, offers a captivating journey that allows cyclists to immerse themselves in the region’s beauty and historical intrigue. Starting in Tuscany, riders traverse rolling hills, verdant vineyards, and medieval towns such as San Gimignano and Monteriggioni, whose ancient architecture and narrow, cobblestone streets transport you back in time. This route draws travellers to keep coming back, and it is easy to see why here are ten reasons to cycle Italy’s most beautiful route.
The Tuscan section of the route is renowned for its picturesque beauty, characterized by cypress-lined roads, olive groves, and quaint villages perched atop hills. Cyclists can enjoy the serene roads that unfold with every turn, making each leg of the journey a visual delight. As the route progresses, the landscape gradually shifts from the lush Chianti region to the Lazio countryside, dotted with historical landmarks and ancient ruins that echo the footsteps of past pilgrims. Approaching Rome, the Eternal City, the Via Francigena, weaves through rural landscapes that offer a sense of tranquillity before reaching Italy’s bustling capital. The Via Francigena is a route that allows cyclists to be modern-day pilgrims and connect with the generations of travellers who have followed this path to Rome.
Our cycling holidays on the Via Francigena
- Tuscany to Rome – Guided Electric Bike Holidays
- Tuscany – Sacred Routes – Self-Guided Mountain Bike Holiday
- Tuscany – Sacred Routes – Guided Mountain Bike Holiday
Lake Garda to Venice
Highlights:
- Two contrasting destinations
- Gentle lakeside cycling
- Discover the unique charm of Venice
Set off on a gentle cycling journey from the southern shores of Lake Garda to the enchanting city of Venice. This route takes you through northern Italy’s stunning natural scenery and hidden Renaissance gems. Begin by exploring the picturesque countryside and charming lake-side towns around Lake Garda, such as the historic Sirmione. As you depart from the lake, you’ll pedal through rural lanes and peaceful back roads on your way to the vibrant city of Verona, following the Adige River, with its scenic canals, lush fields, and vineyards unfolding along the route.
This serene and easy-going path invites you to pause and savour the sights, immersing yourself in the local culture and natural beauty. As you approach your journey’s end, venture toward the Venetian lagoon, finishing with a memorable ride to the delightful town of Chioggia. This cycling adventure not only offers a connection with Italy’s captivating vistas but also a journey that will enhance your understanding and connection with Italian culture. Extend your exploration by beginning in Riva del Garda or enjoying additional time in Venice to deepen your Italian experience.
Our cycling holidays around Lake Garda
- Lake Garda to Venice – Self-Guided Leisure Cycling Holiday
- Lake Garda Explorer – Self-Guided Family Cycling Holiday
- Lake Garda to Venice – Self-Guided Family Cycling Holiday
Find your perfect Italian cycling holiday
Whatever you are looking for from an Italian cycling holiday, you are sure to find it with Skedaddle. From gentle riverside rides to epic mountains, riding in the wheel tracks of professional riders, to sipping prosecco in the shade, a cycling holiday with Skedaddle will make your Italian cycling dreams come true.
Check out our full selection of holidays and choose from our wide range of guided and self-guided trips, select the departure dates, trip grade and level of difficulty that is right for you, and start your journey to discovering the best cycling in Bella Italia!