Cycling Holidays Italy
As specialists in Italian cycling holidays, we create unforgettable experiences with carefully selected routes in some of the most spectacular regions of Italy, paired with food, wine and cultural journeys which amaze and delight.
We pride ourselves on creating varied and very local experiences, both on and off the bike – not settling for the most obvious ride route, the most accessible and reachable restaurant, or the common experience, we move beyond the tourist curtain.
The experience with us is all in the detail.
If you’re looking for a change of pace and love a challenge with great reward, then join us for an Italian cycling holiday like no other.
We offer a selection of Italian cycling holidays for experienced cyclists and their non riding partners that deliver sensational riding, a unique non-riding program, our signature hospitality and a lifetime of memories.
Here we present our 2026 Italian Cycling Holiday Collection.
Tour of Puglia
Puglia’s mostly flat landscape is dotted with beautiful small towns in many shades of white, with unique architecture like the conical trulli of the Valle d’Itria and the extravagant baroque of Lecce in the Salento. This backdrop, together with its quiet roads winding past ancient rock walls and olive groves, and coastal roads that hug the beautiful and diverse coastline of the Ionian and Adriatic Seas, makes it the perfect place to explore on a bike. Join us as we cycle through this land of discovery and adventure, seeking out the hidden gems of the region’s very authentic and rustic food and wine culture, and embracing the warm welcome of its land and people.
This is where the real adventure starts. Explore the roads you never knew existed and take on an occasional climb, surrounded by spectacular scenery and dramatic views. You can expect longer days in the saddle, safe in the knowledge that you will be supported at all times.
Click here for more information on the ride difficulty.
Difficulty Level: Rated 6 / 10
Tour of Tuscany
Tuscany is where our passion for Italian cycling tours was born and the region holds a special place in our hearts. Tuscany is considered the birthplace of the Italian Renaissance and has long enthralled the world with its picture perfect landscapes of sunflower fields, lush valleys and continual rolling hills. It is also cycling heaven, with winding country roads interspersed with olive groves, medieval towns and world-famous wineries bathed in a warm summer sun. Join us as we cycle our way along our favourite roads and past sensational trattorias to forge unforgettable Tuscan memories.
This is where the going gets tough, with longer, harder riding through more challenging and varied terrain. Expect some tough climbs but with beautiful descents on the other side. Click here for more information on the ride difficulty.
Difficulty Level: Rated 8 / 10
Tour of Sardinia
Sardinia is a cycling haven. With beautiful roads, rugged mountains and a coastline of pristine white sand beaches and water in a million shades of turquoise and sapphire, you’ll feel like you’re rolling into paradise every day. Expect diverse landscapes, old towns of Spanish and Arab influence, a daily immersion into the life of true artisans, and the deep history and culture of the Sardo people. Join us as we cycle from the west coast to the east, and along the way, weave amongst tiny backroads and small hamlets, to discover the authentic central heart of the island where hospitality reigns supreme. .
This is a tour with longer days and more hills. Expect a couple of long but steady climbs with descents that are mostly open and free flowing. Click here for more information on the ride difficulty
Difficulty Level: Rated 7 / 10
The Best of Sicily
Traversing the island from west to east on this tour, you’ll venture from the sea and saltpans to rugged landscapes and mountain crests, be immersed amongst ancient temples and picturesque villages, enjoy rides along beautiful coastal routes and quiet country roads, be surrounded by sun-drenched olive groves and orange orchards, and of course enjoy the encounter with the gentle giant herself – Mount Etna – as the culmination to our tour.
These are the most challenging tours we offer. Serious training is required to get the most out of these adventures, and will challenge even the most capable riders. Click here for more information on the ride difficulty.
Difficulty Level: Rated 9 / 10
Stelvio & Dolomites Tour
If your bike bucket list includes many of the famous climbs of Italy, then this tour is for you.
Test yourself across the north Italian mountains. After a warm up on Cancano, you’ll take on Livigno, the iconic Passo dello Stelvio and Gavia, before heading to the Dolomites to tick off Passo di Gardena, Passo Sella, Passo Pordoi, Passo di Campolongo, Colle Santa Lucia, Passo Giau, Passo Falzarego and Passo Valparola.
These are the most challenging tours we offer. Serious training is required to get the most out of these adventures, and will challenge even the most capable riders. Click here for more information on the ride difficulty.
Difficulty Level: Rated 9 / 10
Giro d’Italia & The Great Climbs
Truly stunning vistas and crisp mountain air are hallmarks of the Giro d’Italia as it winds its way through The Alps, the Dolomites and the Apennines. Join us as we tackle the challenges of awe inspiring mountain ascents and thrilling descents as we wind our way through some of Italy’s great rides and climbs. Your Giro d’Italia bike tour will see you follow the same route as the Pros during the first week of the race, while also experiencing the culture, food, wine and hospitality that Italy is famed for.
These are the most challenging tours we offer. Serious training is required to get the most out of these adventures, and will challenge the most capable riders. Click here for more information on the ride difficulty.
Difficulty Level: Rated 9 / 10
Our deep experience in running cycling holidays over 10 years has seen us also deliver tours for:
Tour of Piemonte
Enjoy the exhilaration of cycling through the little-known paradise of Piedmont with its picturesque winding roads that traverse the UNESCO World Heritage region of Le Langhe and the Cottian and Maritime Alps with climbs made famous by the Giro d’Italia and two of the local protagonists, Girardengo and Coppi.
This is your opportunity to join us as we cycle this stunning landscape and partake in produce from an area famous for its gastronomy, slow food ethos, cheeses, wines and white truffles.
Tip your cap in honour of Fausto Coppi, the Champion of Champions, as we lead you on a cycling and culinary adventure of a lifetime.
These are the most challenging tours we offer. Serious training is required to get the most out of these adventures, and will challenge even the most capable riders. Click here for more information on the ride difficulty.
Difficulty Level: Rated 8 / 10
L’Eroica & Tuscany
L’Eroica takes place in Gaiole in Chianti and is dedicated to the golden age of cycling where participants are encouraged to don vintage cycling gear and ride pre ’87 steel bikes along old Roman roads that include gravel roads.
L’Eroica is a cycling event like no other, a sell-out, once in a lifetime ride that combines gruelling hill climbs with the tranquillity and mystique of candle lit pathways and traditional meals that encapsulate the emotion of the festival.
Our week-long cycling holiday fuses memorable days on the bike amongst rolling landscapes with delectable lunches and dinners of the finest Tuscan cuisine.
This is where the going gets tough, with longer, harder riding through more challenging and varied terrain. Expect tough climbs as well as some tricky descents. Click here for more information on the ride difficulty.
Difficulty Level: Rated 8 / 10
While we’re not running cycling holidays for these events and destinations in 2026, contact us if you’re interested in a custom private tour for your group across any of these destination cycling events, or to register your interest in a scheduled tour from 2027.
