Check out our range of road cycling tours in Italy and you’ll find a little something for all levels and abilities. The Skedaddle Italia team are a passionate bunch and excited to share their love and knowledge for this beautiful country. With fantastic on-hand support and expert local advice, our cycling tours of Italy offer the very best experience possible. The mighty Dolomites will suit those after a challenging tour, whilst the Lakes of Lombardia and Tuscany will attract those after a less 'full-on' trip, but in equally stunning surroundings. For those looking for rolling coastal road cycling, riders will love Sardinia and if you want a great insight into the length and breadth of Italy, why not try our iconic journey, the Grand Traverse. Cycling in Italy is an experience not to be missed.
25 Years of Pedallin' Passion
Find Your Ride
We found 15 Holidays in your search for:
- In Italy or Tuscany
- Road Cycling (All Grades)
Destinations (2)
Types of Cycling / Grades (1)
Departure Month
Level of Support
Destinations (2)
Types of Cycling / Grades (1)
Departure Month
Level of Support
Alps and Dolomites - Giants of the Giro
Guided Road Bike Tour
| Start Date | End Date | Price p.p. |
|---|---|---|
| * 29/07/2023 | 06/08/2023 | $2,875.00 |
- Cycling through stunning mountain scenery
- 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
Coast to Coast - L'Adriatico al Tirreno
Guided Road Bike Tour
| Start Date | End Date | Price p.p. |
|---|---|---|
| 20/05/2023 Guaranteed | 28/05/2023 | $2,930.00 |
| 17/06/2023 | 25/06/2023 | $3,160.00 |
| 16/09/2023 | 24/09/2023 | $2,930.00 |
- 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
Lakes of Lombardia
Guided Road Bike Tour
| Start Date | End Date | Price p.p. |
|---|---|---|
| 15/07/2023 | 22/07/2023 | $2,835.00 |
| 12/08/2023 | 19/08/2023 | $2,835.00 |
- 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
Puglia - The Beautiful South
Guided Road Bike Tour
| Start Date | End Date | Price p.p. |
|---|---|---|
| 06/05/2023 | 13/05/2023 | $2,525.00 |
| 07/10/2023 Contact Us | 14/10/2023 | $2,525.00 |
- Enjoying the panoramic coastal road between Santa Maria di Leuca and Otranto
- Admiring the baroque style churches of Lecce
- Exploring the gnarled olive groves in the countryside around Alberobello
- Enjoying the sights at Alberobello famous for the ‘trulli’
- Visiting 3 UNESCO heritage sites; Lecce, Alberobello and Matera
- Savouring the deep red wine of the Salento region and the crisp whites of Locorotondo
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.
2023 25 Mar – 30 Oct (excluding dates from 18 Jun – 26 Aug)
Season 1 – $1985 25 Mar – 05 Apr, 15 Apr – 17 Jun and 10 Sep – 30 Oct
Season 2 – $2200 06 Apr – 14 Apr and 27 Aug – 09 Sep
- Enjoying the panoramic coastal road between Santa Maria di Leuca and Otranto
- Admiring the Baroque churches of Lecce
- Exploring the gnarled olive groves in the countryside of Alberobello
- Enjoying the sights of Alberobello, famous for the ‘trulli’
- Visiting 3 UNESCO heritage sites; Lecce, Alberobello and Matera
- Savouring the deep red wine of the Salento region and the crisp whites of Locorotondo
Grand Traverse Classic - North to South
Guided Road Bike Tour
| Start Date | End Date | Price p.p. |
|---|---|---|
| 25/05/2023 | 10/06/2023 | $5,270.00 |
| 21/09/2023 Fully Booked | 07/10/2023 | $5,270.00 |
- 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!
Tuscany - Giro della Toscana
Guided Road Bike Tour
| Start Date | End Date | Price p.p. |
|---|---|---|
| 13/05/2023 | 20/05/2023 | $2,430.00 |
| 10/06/2023 | 17/06/2023 | $2,430.00 |
| 09/09/2023 | 16/09/2023 | $2,430.00 |
- 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
Sardinia - Coastal Explorer
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.
2023 25 Mar – 30 Oct (excluding dates from 18 Jun – 26 Aug)
Season 1 – $1855 25 Mar – 05 Apr, 15 Apr – 17 Jun and 10 Sep – 30 Oct
Season 2 – $2160 06 Apr – 14 Apr and 27 Aug – 09 Sep
- 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
Grand Traverse Explorer - South to North
Guided Road Bike Tour
| Start Date | End Date | Price p.p. |
|---|---|---|
| 29/04/2023 | 20/05/2023 | $6,675.00 |
| 26/08/2023 Guaranteed | 16/09/2023 | $6,675.00 |
- 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!
Italy
Prosecco Hills
Self-Guided Road Bike Tour
Duration
8 daysPrices from
$1,820 P.P.
Grade 2 : Gentle
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.
2023 22 Apr – 30 Oct
Season 1 – $1820 22 Apr – 17 Jun and 04 Sep – 30 Oct
Season 2 – $1890 18 Jun – 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”
Prosecco Hills
Guided Road Bike Tour
| Start Date | End Date | Price p.p. |
|---|---|---|
| 17/06/2023 Fully Booked | 24/06/2023 | $2,510.00 |
| 26/08/2023 | 02/09/2023 | $2,510.00 |
- Beautifully scenic cycling in the UNESCO vineyards of Prosecco
- Plenty of opportunities for wine tasting at the end of a day’s ride
- Superb regional cuisine with terraced osterias overlooking vineyards
- Pretty medieval towns and historic castles
- Wandering through picturesque villages and towns such as Follina and Asolo
- Taking a stroll over the famous Bassano del Grappa bridge
Sardinia - Coastal Explorer
Guided Road Bike Tour
| Start Date | End Date | Price p.p. |
|---|---|---|
| 27/05/2023 | 03/06/2023 | $2,295.00 |
| 02/09/2023 | 09/09/2023 | $2,295.00 |
| 07/10/2023 | 14/10/2023 | $2,295.00 |
- 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
Dolomiti Discoverer
Guided Road Bike Tour
| Start Date | End Date | Price p.p. |
|---|---|---|
| 01/07/2023 Guaranteed | 08/07/2023 | $2,700.00 |
| 22/07/2023 | 29/07/2023 | $2,700.00 |
- 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!
Tuscany - Giro della Toscana
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.
2023 26 Mar – 30 Oct
Season 1 – $1985 25 Mar – 05 Apr, 15 Apr – 17 Jun and 04 Sep – 30 Oct
Season 2 – $2295 06 Apr – 14 Apr and 18 Jun – 03 Sep
SPECIAL 2023 OFFER! Book now and make savings on our Giro della Toscana tour. Please quote code EM2023 at the time of booking your trip to get 5% off. *T&Cs apply, offer ends 1/31/2023.
- 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
Sardinia - Coast to Coast
Self-Guided Road Bike Tour
| Start Date | End Date | Price p.p. |
|---|---|---|
| 29/04/2023 | 06/05/2023 | $1,670.00 |
| 30/09/2023 | 07/10/2023 | $1,670.00 |
Daily departures available. The season prices below are per person and are applicable for all start dates between and inclusive of the stated dates.
2023 25 Mar – 30 Oct (excluding dates from 18 Jun – 26 Aug)
Season 1 – $1880 25 Mar – 05 Apr, 15 Apr – 17 Jun and 10 Sep – 30 Oct
Season 2 – $2050 06 Apr – 14 Apr and 27 Aug – 09 Sep
Alternatively for a great value holiday choose 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 the Orosei Gulf
- Cycling just below the Perda Liana mountain range
- Dining on delicious home cooked food, washed down with tasty local wine!
- Enjoying the speedy descent to Cala Gonone on the east coast