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 (2)
Types of Cycling / Grades (1)
Departure Month
Level of Support
Destinations (2)
Types of Cycling / Grades (1)
Departure Month
Level of Support
Page 1 of 2
Select Order
Order By
Guided
Alps and Dolomites - Giants of the Giro
Guided Road Bike Tour
| Start Date | End Date | Price p.p. |
|---|---|---|
| 25/07/2025 Guaranteed | 02/08/2025 | $3,345.00 |
| 16/08/2025 | 24/08/2025 | $3,345.00 |
- 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
Coast to Coast - L'Adriatico al Tirreno
Guided Road Bike Tour
| Start Date | End Date | Price p.p. |
|---|---|---|
| 17/05/2025 | 25/05/2025 | $3,480.00 |
| 07/06/2025 | 15/06/2025 | $3,575.00 |
| 13/09/2025 | 21/09/2025 | $3,480.00 |
- 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
Lakes of Lombardia
Guided Road Bike Tour
| Start Date | End Date | Price p.p. |
|---|---|---|
| 12/07/2025 | 19/07/2025 | $3,250.00 |
| 02/08/2025 | 09/08/2025 | $3,250.00 |
- 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
Self-Guided
Puglia - The Beautiful South
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.
2024 25 Mar – 30 Oct (excluding dates from 09 Jun – 31 Aug)
Season 1 – $2140 03 Apr – 08 Jun / 10 Sep – 30 Oct
Season 2 – $2345 25 Mar – 02 Apr / 01 Sept – 09 Sept
2025 24 Mar – 29 Oct (excluding dates from 09 Jun – 31 Aug)
Season 1 – $2250 24 Mar – 08 Jun / 09 Sep – 29 Oct
Season 2 – $2465 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
Guided
Grand Traverse Classic - North to South
Guided Road Bike Tour
| Start Date | End Date | Price p.p. |
|---|---|---|
| 22/05/2025 | 07/06/2025 | $5,965.00 |
| 25/09/2025 | 11/10/2025 | $5,965.00 |
- 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
Tuscany - Giro della Toscana
Guided Road Bike Tour
| Start Date | End Date | Price p.p. |
|---|---|---|
| 03/05/2025 | 10/05/2025 | $2,765.00 |
| 31/05/2025 | 07/06/2025 | $2,765.00 |
| 30/08/2025 | 06/09/2025 | $2,765.00 |
- 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
Guided
Grand Traverse Explorer - South to North
Guided Road Bike Tour
.png)
SAVE ON 2025 EARLY SEASON ESCAPES
Book before 31 October 2024 to get $325 off your tour departing on 26/04/2025. Apply promo code FYR2025.
| Start Date | End Date | Price p.p. |
|---|---|---|
| * 26/04/2025 | 17/05/2025 | $7,690.00 |
| 23/08/2025 | 13/09/2025 | $7,690.00 |
- 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!
Self-Guided
Sardinia - Coastal Explorer
Self-Guided Road Bike Tour
.png)
SAVE ON 2025 EARLY SEASON ESCAPES
Book before 31 October 2024 to get $100 off your holiday departing in Spring 2025 before April 30th. Apply promo code FYR2025.
Daily departures available. The season prices below are per person and are applicable for all start dates between and inclusive of the stated dates.
2024 25 Mar – 30 Oct (excluding dates from 09 Jun – 31 Aug)
Season 1 – $1895 03 Apr – 08 Jun and 10 Sep – 30 Oct
Season 2 – $2175 25 Mar – 02 Apr and 01 Sept – 09 Sept
2025 24 Mar – 29 Oct (excluding dates from 09 Jun – 31 Aug)
Season 1 – $1990 24 Mar – 08 Jun and 09 Sep – 29 Oct
Season 2 – $2290 01 Sept – 08 Sept
SAVE ON 2025 EARLY SEASON ESCAPES!
Book your early cycling escape before the 31st of October and save $100. Applies to departures between the 24th March and the 30th April 2025. Apply the promo code FYR2025 when you book. Your discount will be applied once your booking is confirmed.
- 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 descent to Fluminimaggiore and Masua
- Exploring the white beaches running alongside the south west coastal road
Self-Guided
Tuscany - Giro della Toscana
Self-Guided Road Bike Tour
.png)
SAVE ON 2025 EARLY SEASON ESCAPES
Book before 31 October 2024 to get $100 off your holiday departing in Spring 2025 before April 30th. Apply promo code FYR2025.
Daily departures available. The season prices below are per person and are applicable for all start dates between and inclusive of the stated dates.
2024 25 Mar – 30 Oct (excluding dates throughout July and August)
Season 1 – $2165 03 Apr – 17 Jun and 04 Sep – 30 Oct
Season 2 – $2480 25 Mar – 02 Apr, 18 Jun – 30 Jun and 01 – 03 Sep
2025 24 Mar – 29 Oct (excluding dates throughout July and August)
Season 1 – $2275 24 Mar – 16 Jun and 03 Sep – 29 Oct
Season 2 – $2615 17 Jun – 30 Jun and 01 – 02 Sep
SAVE ON 2025 EARLY SEASON ESCAPES!
Book your early cycling escape before the 31st of October and save $100. Applies to departures between the 24th March and the 30th April 2025. Apply the promo code FYR2025 when you book. Your discount will be applied once your booking is confirmed.
- 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
Self-Guided
Prosecco Hills
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.
2024 22 Apr – 30 Oct (no departures in July and August)
Season 1 – $1530 22 Apr – 17 Jun and 04 Sep – 30 Oct
Season 2 – $1730 18 Jun – 30 Jun and 01 – 03 Sep
- Riding over rolling hills through Prosecco vineyards
- Stopping off for lunch at a terraced osteria overlooking stunning scenery
- Visiting the water mill of Molinetto della Croda
- Strolling through picturesque villages and towns such as Follina and Asolo
- Exploring the fascinating caves, cascading waterfalls and surrounding park of Grotte del Caglieron
- Enjoying the buzz of Bassano del Grappa and strolling over the wooden bridge of “Ponte degli Alpini”
Road Cycling Vacations & Tours In Italy
-italy-road-cycling-holiday.jpg)
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.
You Might Also Like...
News, Reviews & Stories
The Story Behind Sardinia Cape to Cape
Exploring Sardinia's incredible off road gravel trails on our unique Cape to Cape adventure.
Meet our local partners in Prosecco
Discover the story behind our new Italian holidays and meet Giovanni, your expert on the local Prosecco region...