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 (10)
Types of Cycling / Grades (1)
Departure Month
Level of Support
Destinations (10)
Types of Cycling / Grades (1)
Departure Month
Level of Support
Types of Cycling in Italy
Leisure Cycling in Italy
A range of grades on scenic routes, perfect for soaking up Italy’s landscapes, culture and cuisine at a relaxed pace.
Road Cycling in Italy
Tackle legendary climbs, quiet backroads and iconic routes in the heartland of Italian cycling culture.
Mountain Biking in Italy
Ride adrenaline-filled off-road trails through mountains, forests and rugged terrain made for adventure.
Gravel Riding in Italy
Explore Italy’s historic white roads and remote countryside on unforgettable mixed-surface routes.
Road Cycling in Italy Destination Guide
Italy is a dream for road cyclists. Whether you’re planning a self-guided bicycle tour in Italy, guided bike touring, or an immersive road cycling holiday , the country offers routes that combine challenging climbs, flowing descents, and unforgettable scenery.
Tuscany – Rolling hills, quiet lanes, and iconic landscapes make Tuscany ideal for road bike tours in Italy. Routes through Chianti and Val d’Orcia deliver rhythmical climbs and scenic descents perfect for long days in the saddle.
Dolomites – Legendary alpine climbs of the Giro d’Italia and dramatic switchbacks make the Dolomites a must for serious road cycling holidays in Italy. Passes like the Sella Ronda and Giau are bucket-list climbs for every road cyclist.
Sardinia – Smooth roads, low traffic, and scenic coastal stretches make Sardinia perfect for bike touring in Italy.
Piedmont – Vineyard climbs, cycling heritage, and quiet tarmac create an authentic bicycle tour in Italy.
Veneto – From rolling hills to flatter plains, Veneto offers variety for every road bike Italy rider.
Puglia – Gently undulating roads and sun-soaked coastal routes make Puglia perfect for early- and late-season road cycling holidays in Italy.
Cilento - The Coast adds dramatic roller-coaster ride and breath-taking views, ideal for riders seeking a truly unforgettable road cycling holiday in Italy.
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Self-Guided
Self-Guided
Italy
NEW! - Piedmont - La Strada del Vino
Self-Guided Road Cycling Holiday
Duration
8 daysPrices from
£1,595 P.P.
Grade 3 : Moderate
NEW! - Piedmont - La Strada del Vino
Self-Guided Road Cycling Holiday
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 (no departures in July and August)
Season 1 – £1595 18 Apr – 14 Jun / 09 Sep – 26 Oct
Season 2 – £1795 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!
Guided
Guided
Italy
NEW! - Piedmont - La Strada del Vino
Guided Road Cycling Holiday
Duration
8 daysPrices from
£1,995 P.P.
Grade 3 : Moderate
NEW! - Piedmont - La Strada del Vino
Guided Road Cycling Holiday
| Start Date | End Date | Price p.p. |
|---|---|---|
| 06/06/2026 Fully Booked | 13/06/2026 | £1,995.00 |
| 12/09/2026 | 19/09/2026 | £1,995.00 |
- 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!
Guided
Coast to Coast - L'Adriatico al Tirreno
Guided Road Cycling Holiday
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EARLY SEASON SAVINGS
Save £100 when you book our tour departing 16 May 2026. Book before 16 February and enter promo code SPRING26. Your discount will be applied once your booking is confirmed. Ts and Cs apply.
| Start Date | End Date | Price p.p. |
|---|---|---|
| * 16/05/2026 Guaranteed | 24/05/2026 | £2,695.00 |
| 12/09/2026 Guaranteed | 20/09/2026 | £2,695.00 |
- An epic coast to coast journey riding all the way from the Adriatic coast to the Tyrrhenian Sea
- Cycling through the smallest republic in Europe, San Marino
- Easing along the rolling Nove Colli hills, the routes of the famous Italian Gran Fondo
- Visiting historical sites such as the Palazzo Ducale in Orvieto and San Francis Abbey in Assisi
- Staying in quality accommodation, with fantastically warm hospitality
- Riding to Gubbio and Assisi, UNESCO World Heritage sites
Guided
Grand Traverse Classic - North to South
Guided Road Cycling Holiday
| Start Date | End Date | Price p.p. |
|---|---|---|
| 21/05/2026 Last Spaces | 06/06/2026 | £4,195.00 |
| 24/09/2026 Guaranteed | 10/10/2026 | £4,195.00 |
- Riding down 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: Lucca, San Gimignano, Pienza, Assisi and Lecce
- 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 to the most southerly point of Italy, having ridden nearly 1,100 miles and climbed over 21,000 metres!
Guided
Sardinia - Coastal Explorer
Guided Road Cycling Holiday
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EARLY SEASON SAVINGS
Save £100 when you book our tour departing 9 or 23 May 2026. Book before 16 February and enter promo code SPRING26. Your discount will be applied once your booking is confirmed. Ts and Cs apply.
| Start Date | End Date | Price p.p. |
|---|---|---|
| * 09/05/2026 Guaranteed | 16/05/2026 | £2,125.00 |
| * 23/05/2026 Guaranteed | 30/05/2026 | £2,125.00 |
| 19/09/2026 Fully Booked | 26/09/2026 | £2,125.00 |
| 10/10/2026 | 17/10/2026 | £2,125.00 |
- 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
Self-Guided
Puglia - The Beautiful South
Self-Guided Road Cycling Holiday
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 – £1695 29 Mar – 07 Jun / 09 Sep – 26 Oct
Season 2 – £1955 01 Sept – 08 Sept
- Savouring the deep red wine of the Salento region and the crisp whites of Locorotondo
- Enjoying the sights of Alberobello, famous for the ‘trulli’
- Exploring the gnarled olive groves in the countryside of Alberobello
- Visiting 2 UNESCO heritage sites; Lecce and Alberobello
- Admiring the Baroque churches of Lecce
- Enjoying the panoramic coastal road between Santa Maria di Leuca and Otranto
Self-Guided
Sardinia - Coastal Explorer
Self-Guided Road Cycling Holiday
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 – £1475 26 Mar – 07 Jun and 09 Sep – 29 Oct
Season 2 – £1685 01 Sept – 08 Sept
- Riding the stunning coastal road from Alghero to Bosa
- Exploring the sandstone coast of Santa Caterina di Pittinuri
- Visiting the Sinis Peninsula and the ancient Roman ruins of Tharros
- The view of Pan di Zucchero on the Nebida coastal ride
- Sweeping down the long descents to Fluminimaggiore and Masua
- Exploring the white beaches running alongside the south west coastal road
Self-Guided
Tuscany - Giro della Toscana
Self-Guided Road Cycling Holiday
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 in July and August)
Season 1 – £1795 29 Mar – 14 Jun and 09 Sep – 26 Oct
Season 2 – £2095 15 Jun – 30 Jun and 01 – 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 the historic wine regions of Tuscany, stopping off for a bit of wine tasting along the way
- Staying in quality accommodation, with fantastically warm hospitality
- Easing along the rolling hills of the ‘Colli Sienesi’
- Riding the stunning UNESCO heritage region of Val d’Orcia
- Stopping off at the lovely San Gimignano and Montalcino
- Chilling out with a post-ride Chianti
Guided
Alps and Dolomites - Giants of the Giro
Guided Road Cycling Holiday
| Start Date | End Date | Price p.p. |
|---|---|---|
| 25/07/2026 Guaranteed | 02/08/2026 | £2,495.00 |
| 22/08/2026 | 30/08/2026 | £2,495.00 |
- Cycling through the best alpine and dolomite scenery of Italy
- Climbing the iconic Mortirolo, Passo Gavia and Passo Stelvio of Giro d’Italia fame
- Enjoying post-ride relaxation in typical chalet-style mountain hotels
- Re-charging your energy levels every evening with tasty local fayre
- Testing your legs and endurance on the final Monte Grappa climb
- Enjoying an aperitif in the lively towns of San Pellegrino Terme, Bormio and Bassano del Grappa
Guided
Tuscany - Giro della Toscana
Guided Road Cycling Holiday
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EARLY SEASON SAVINGS
Save £100 when you book our tour departing 2 May 2026. Book before 16 February and enter promo code SPRING26. Your discount will be applied once your booking is confirmed. Ts and Cs apply.
| Start Date | End Date | Price p.p. |
|---|---|---|
| * 02/05/2026 Guaranteed | 09/05/2026 | £2,095.00 |
| 31/05/2026 | 07/06/2026 | £2,095.00 |
| 29/08/2026 | 05/09/2026 | £2,095.00 |
| 03/10/2026 Guaranteed | 10/10/2026 | £2,095.00 |
- Cycling through the historic wine regions of Tuscany, stopping off for a bit of wine tasting along the way
- Staying in quality accommodation, with fantastically warm hospitality
- Easing along the rolling hills of the Colli Sienesi
- Riding the stunning UNESCO heritage region of Val d’Orcia
- Stopping off at the lovely San Gimignano and Montalcino
- Chilling out with a post-ride Chianti
Not sure which trip's right for you? Just ask!
Get in touch and we'll help you find your perfect trip.
Road Cycling Holidays & Tours In Italy
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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 and Piedmont. 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.
Coast to Coast
Ride the L’Adriatico al Tirreno route, pedalling from the Adriatic to the Tyrrhenian Sea through rolling hills and historic towns.
Explore Tuscany
Giro della Toscana, where quiet vineyard roads and gentle climbs wind through Chianti and Val d’Orcia — a perfect road bike Italy.
Island Riding
The Sardinia – Coastal Explorer offers stunning cliffside roads and sweeping descents. Each route is ideal for a bicycle tour, bike touring, or a memorable road cycling holiday in Italy.
High-Mountain Drama
Ride Italy’s iconic Stelvio, Gavia, and Mortirolo, with dramatic switchbacks and soaring alpine views — a true bucket-list cycling adventure.
Road Cycling in Italy – Conditions
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Italy’s roads are generally smooth and well maintained, with quiet country lanes, scenic secondary roads, and a growing network of marked cycle routes in Tuscany, Veneto, and Piedmont. Traffic varies: alpine and rural routes are peaceful, while cities and coastal towns are busier. Italians have a warm cycling culture, often friendly to riders, especially in rural areas.
Gradients range from gentle rolling hills to challenging alpine climbs, offering diverse terrain for road bike enthusiasts in Italy seeking both endurance and scenic reward.
Expect a Mediterranean climate with hot summers and mild spring and autumn rides, and cooler mountain rides.
Road Cycling Holidays & Tours in Italy
Italy is the ultimate destination for road cycling holidays, offering a unique blend of scenic landscapes, iconic climbs, and cultural richness. From the rolling vineyards of Tuscany to the epic switchbacks of the Dolomites and the sun-drenched coastal roads of Sardinia and the Cilento Coast, every route is designed to reward riders with memorable experiences and unforgettable views.
Who it’s for: Cycling in Italy suits riders of all levels. Enthusiasts seeking legendary climbs and long days in the saddle will find the Dolomites or Tuscany both challenging and exhilarating. At the same time, those who prefer relaxed, scenic routes can enjoy flatter coastal roads in Sardinia. Italy is also perfect for bicycle touring, with guided or self-guided options that let you tailor the experience to your pace and ambitions.
Grades: Tours are graded from moderate to challenging, ensuring everyone can find a route that suits their fitness and experience. Whether you’re building endurance, chasing iconic climbs, or simply riding for the joy of it, Italy offers a road cycling holiday that is thrilling and accessible.
Can I hire a bike in Italy?
Yes! All Skedaddle tours offer high-quality road bike hire in Italy, so you can enjoy a properly fitted bike without the hassle of travelling with your own. Typically we offer Giant Defy Advanced or Liv Avail Advanced for hire but please check the Bike Hire section of the holiday you are interested in to find out more.
Can I travel with my own bike?
You can, though we recommend checking airline requirements for packing and insurance. Many riders find it easier to hire a bike locally, avoiding the stress of transport and potential damage to their own precious bike.
What’s the terrain and challenge like in the Dolomites?
The Dolomites are iconic in the cycling world, hosting many Giro d’Italia stages. Expect steep alpine climbs, hairpin descents, and dramatic scenery. Rides are challenging yet rewarding, offering some of the most memorable road-cycling experiences in Italy for serious cyclists.
What if I’m not ready to book yet?
Sign up for detailed trip notes or register your interest. You’ll get daily elevation, distance, terrain descriptions, and tips — all designed to help you decide whether a road cycling holiday in Italy is right for you. Give us a call. Our office team is full of passionate cyclists who have done many Skedaddle trips themselves.
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