Italy is home to some incredible road cycling and our Skedaddle Italia team have spent decades perfecting our tours here. Head into the mighty Dolomites and you can follow in the wheel tracks of cycling legends as you take on some of the most famous Alpine climbs like Stelvio, Motirolo and Sella Ronda. Those in search of a moderately challenging ride through scenic landscapes will love our road cycling holidays in Tuscany, Puglia and Lombardy. Meanwhile, Sardinia is a dream riding destination, with its quiet roads snaking past rugged coastlines and beautiful white sandy beaches. For the ultimate ‘grand tour’ why not ride the entire backbone of Italy on our Grand Traverse over two or three weeks?
.png)
Destinations (8)
Types of Cycling / Grades (1)
Departure Month
Level of Support
Destinations (8)
Types of Cycling / Grades (1)
Departure Month
Level of Support
Road Cycling in Italy Destination Guide
We’ve been delivering incredible cycling holidays in Italy for over 20 years! Our passionate local teams are second to none and can’t wait to welcome you.
Tuscany: The iconic Tuscan landscapes cannot fail to captivate the soul! We’re taking cypress trees, endless fields of rippling corn and world-class cultural wonders galore...
The Dolomites: Are you seeking challenging mountain hill climbs and thrilling descents? Don’t miss our challenging cycling holidays in the Dolomites then!
Sardinia: This wild, rugged island is one of our absolute favourites and the home of Skedaddle Italia. Our cycling holidays here offer something for everyone!
Prosecco Region: This destination offers great road cycling with its quiet roads, rolling vineyard-lined hills, and also treats you to some of the best food and wine in Italy.
Page 2 of 2
Select Order
Order By
Guided
NEW! Coast to Coast - Puglia to Cilento
Guided Road Cycling Holiday
| Start Date | End Date | Price p.p. |
|---|---|---|
| 28/09/2025 Guaranteed | 05/10/2025 | £1,995.00 |
| 06/10/2025 Guaranteed | 13/10/2025 | £1,995.00 |
- An epic coast to coast journey through southern Italy riding from the Adriatic coast to the Tyrrhenian Sea
- Exploring the UNESCO World Heritage sites of Alberobello, Matera, Padula and Paestum
- Losing ourselves in the labyrinthic white washed alleyways of Noci and Tricarico
- Climbing the hills of little-known Basilicata, to the hill-top villages of Castelmezzano, Calvello and Marsico Vetere
- Cycling through the Dolomiti Lucane, southern Italy’s lesser-known Dolomites
- Enjoying the roller-coaster ride along the Cilento Coast from Palinuro to Paestum
- Sampling southern Italy’s best food and wine
Guided
Guided
Czech Republic, Austria, Slovenia & Italy
NEW! Prague to Venice
Guided Road Cycling Holiday
Duration
21 daysPrices from
£5,495 P.P.
Grade 3 : Moderate
NEW! Prague to Venice
Guided Road Cycling Holiday
| Start Date | End Date | Price p.p. |
|---|---|---|
| 05/07/2025 Last Spaces | 25/07/2025 | £5,495.00 |
| 06/06/2026 Last Spaces | 26/06/2026 | £5,775.00 |
| 04/07/2026 Fully Booked | 24/07/2026 | £5,775.00 |
| 01/08/2026 Fully Booked | 21/08/2026 | £5,775.00 |
- A journey from Central Europe to the Mediterranean through four European countries
- Visit the vibrant capitals of Prague, Vienna and Ljubljana
- Learn about the historical Central European regions of Bohemia and Styria
- Explore the UNESCO World Heritage sites of Prague, Cesky Krumlov, Vienna, Graz, and Venice
- Have a well deserved end-of-ride pilsner seated in the village square of a little Bohemian village
- Enjoy quiet countryside roads with sweeping views all the way from Prague to Vienna
- Staying in quality accommodation, with warm traditional hospitality
- Feast on the traditional dishes, desserts and drinks of the Czech, Austrian and Slovenian cuisine.
Guided
Grand Traverse Explorer - South to North
Guided Road Cycling Holiday
| Start Date | End Date | Price p.p. |
|---|---|---|
| * 23/08/2025 Guaranteed | 13/09/2025 | £5,595.00 |
| 25/04/2026 | 16/05/2026 | £5,875.00 |
| 29/08/2026 | 19/09/2026 | £5,875.00 |
- Riding up the backbone of Italy on a stunning route which takes in some of the best road cycling that Italy has to offer
- Cycling through 10 UNESCO World Heritage sites and 5 National Parks
- Visiting some of the most important historical and artistic cities in Italy: Lecce, Assisi, Siena, Venice
- The camaraderie of your fellow cyclists who’ll be joining you on this incredible tour
- Immersing yourself in Italian culture – meeting the friendly locals, experiencing delicious culinary specialties and tasting the wines of each region
- Cycling from the most south-easterly point of the heel of Italy up to Venice, having ridden nearly 1,100 miles and climbed almost 22,000 metres!
Guided
Lakes of Lombardia
Guided Road Cycling Holiday
| Start Date | End Date | Price p.p. |
|---|---|---|
| * 12/07/2025 Guaranteed | 19/07/2025 | £2,395.00 |
| * 02/08/2025 Contact Us | 09/08/2025 | £2,395.00 |
- Riding into Switzerland from Lake Maggiore to Lake Lugano
- The ascent to Madonna del Ghisallo and the world famous cycling museum
- Strolling through Bellagio on Lake Como after a great lake-side ride
- Conquering Passo Maniva and the sweeping downhill to Lago di Idro
- Relaxing with a post-ride drink overlooking yet another beautiful lake
- Enjoying good food, fine wines and quality accommodation
Road Cycling Holidays & Tours In Italy
-italy-road-cycling-holiday.jpg)
Why choose Italy for your road cycling holiday?
The varying landscapes of Italy offer something for road cyclists of all abilities, with endless coastal views, mountain challenges, and rolling hills dotted with vineyards. Our Italia team has spent more than 20 years seeking out the best road cycling across Italy, ensuring an exceptional experience for your Italian cycle holiday and bike tour.
Top destinations for road bike tours in Italy
Discover the finest road cycling Italy has to offer in Tuscany, the Lakes of Lombardia, the Prosecco Region, and Puglia. For those seeking dramatic mountain passes and breathtaking scenery, the Dolomites and Italian Alps are unparalleled in Europe. Coastal road cycling enthusiasts will adore the routes in Sardinia. For a comprehensive exploration of Italy's diverse landscapes, consider embarking on our end-to-end journey, the Grand Traverse.
Decide how you ride
Our road cycling tour range in Italy is designed to suit different types of riders and preferences. Choose your riding grade based on your fitness level. You can also choose between joining a guided small group tour or embarking on a self-guided cycling Italy tour.
You Might Also Like...
News, Reviews & Stories
The Best Cycling Routes in Italy
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.
The Story Behind Sardinia Cape to Cape
Exploring Sardinia's incredible off road gravel trails on our unique Cape to Cape adventure.