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?
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Destinations (9)
Types of Cycling / Grades (1)
Departure Month
Level of Support
Destinations (9)
Types of Cycling / Grades (1)
Departure Month
Level of Support
Road Cycling in Italy Destination Guide
We’ve been delivering incredible cycling tours 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.
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Guided
Prague to Venice
Guided Road Bike Tour
| Start Date | End Date | Price p.p. |
|---|---|---|
| 06/06/2026 Fully Booked | 26/06/2026 | $8,250.00 |
| 04/07/2026 Fully Booked | 24/07/2026 | $8,250.00 |
| 01/08/2026 Fully Booked | 21/08/2026 | $8,250.00 |
| 05/06/2027 Guaranteed | 25/06/2027 | $8,850.00 |
| 03/07/2027 | 23/07/2027 | $8,850.00 |
- 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
Guided
Italy
NEW! - Piedmont - La Strada del Vino
Guided Road Bike Tour
Duration
8 daysPrices from
$2,850 P.P.
Grade 3: Moderate
NEW! - Piedmont - La Strada del Vino
Guided Road Bike Tour
| Start Date | End Date | Price p.p. |
|---|---|---|
| 06/06/2026 | 13/06/2026 | $2,850.00 |
| 12/09/2026 | 19/09/2026 | $2,850.00 |
- Cycling through rolling hills terraced with vineyards and quaint medieval villages
- Capturing beautiful views that stretch as far as the Alps
- Admiring castle topped villages which lend a historic romantic feel to the area
- Tasting some of the best wines in Italy in the regions they are produced; Barolo, Barbaresco and Asti
- Feasting on some of the best regional food in Italy, including truffles, cheeses and hazelnut Gianduia chocolates!
Self-Guided
Self-Guided
Italy
NEW! - Piedmont - La Strada del Vino
Self-Guided Road Bike Tour
Duration
8 daysPrices from
$2,280 P.P.
Grade 3: Moderate
NEW! - Piedmont - La Strada del Vino
Self-Guided Road Bike Tour
Daily departures available between April and October. The season prices below are per person and are applicable for all start dates between and inclusive of the stated dates.
2026 18 Apr – 26 Oct (no departures in July and August)
Season 1 – $2280 18 Apr – 14 Jun / 09 Sep – 26 Oct
Season 2 – $2565 15 Jun – 30 Jun / 01 Sep – 08 Sep
To ensure you have the best experience possible, we’d recommend travelling in the Spring or in the Autumn. We don’t as standard offer this tour in the hotter, more humid, busier summer months of July and August. If however your dates are set in July or August, please call us for a chat and we’ll do what we can to accommodate you.
- Cycling through rolling hills terraced with vineyards and quaint medieval villages
- Capturing beautiful views that stretch as far as the Alps
- Admiring castle topped villages which lend a historic romantic feel to the area
- Tasting some of the best wines in Italy in the regions they are produced; Barolo, Barbaresco and Asti
- Feasting on some of the best regional food in Italy, including truffles, cheeses and hazelnut Gianduia chocolates!
Self-Guided
Sardinia - Coast to Coast
Self-Guided Road Bike Tour
Daily departures available. The season prices below are per person and are applicable for all start dates between and inclusive of the stated dates.
2026 29 Mar – 26 Oct (excluding dates from 08 Jun – 31 Aug)
Season 1 – $2280 29 Mar – 07 Jun / 09 Sep – 26 Oct
Season 2 – $2525 01 Sept – 08 Sept
Alternatively for a great value holiday select one of our scheduled departures below.
- Riding the roller-coaster road below Mount Arcuentu to the west coast
- Exploring the UNESCO heritage site of Su Nuraxi at Barumini
- Taking a dip in the emerald waters of Sardinia
- Cycling through the Sardinian “Blue Zone”
- Dining on delicious home cooked food, washed down with tasty local wine!
- The stunning descent to Bari Sardo on the East Coast
Guided
Sardinia - Coastal Explorer
Guided Road Bike Tour
| Start Date | End Date | Price p.p. |
|---|---|---|
| 09/05/2026 | 16/05/2026 | $2,850.00 |
| 23/05/2026 | 30/05/2026 | $2,850.00 |
| 19/09/2026 Guaranteed | 26/09/2026 | $2,850.00 |
| 10/10/2026 | 17/10/2026 | $2,850.00 |
- Riding the stunning coastal road from Alghero to Bosa
- The ride to Montiferru through its oak forest
- Sampling delightful Sardinian foods with a vast variety of local wines
- Enjoying the view of Pan di Zucchero on the Nebida coastal ride
- Sweeping down the long descent to Fluminimaggiore and Masua
- Glimpsing the white beaches which hug the south west coast road
Guided
Dolomiti Discoverer
Guided Road Bike Tour
| Start Date | End Date | Price p.p. |
|---|---|---|
| 04/07/2026 | 11/07/2026 | $3,750.00 |
| 18/07/2026 | 25/07/2026 | $3,750.00 |
- Admiring from various angles the classic grey and orange jagged peaks of the Dolomites
- Riding the Sella Ronda, part of the Maratona delle Dolomiti, one of Italy’s biggest Gran Fondo events
- Riding the dazzling descents and climbs you yearned to ride whilst watching the Giro d‘Italia
- The sense of achievement at the end of the tour having conquered many climbs at your own pace.
- Superb, mouth-watering and filling Italian food after a day on the bike – plenty of carbs!
Not sure which trip's right for you? Just ask!
Get in touch and we'll help you find your perfect trip.
Road Cycling Vacations & Tours In Italy
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Why choose Italy for your road cycling vacation?
The varying landscapes of Italy offer something for every kind of road cyclist, 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 Italy cycle vacations and bike tours.
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.
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