+44 (0)1506 635399 info@hookedoncycling.co.uk
+44 (0)1506 635399 info@hookedoncycling.co.uk

The Best Cycling Holidays In Italy

Homepage > The Best Cycling Holidays In Italy

Ever wanted to take a cycling holiday in Italy? Now’s the time. At Hooked On Cycling, we’re proud to offer a unique range of guided and self-guided cycling holidays in Italy for both beginners and experienced riders alike. In this helpful guide, we provide key information on each and every one of our brilliant cycling tours in Italy, so you can choose which one is best for you!

Hooked On Cycling Bike Tours In Italy

With over 66 unique tours to choose from covering the entirety of Italy, Hooked on Cycling have an incredible range of cycling holidays in Italy to choose from. Below, we take a closer look at each one in greater detail, highlighting the destinations, duration and unique sights, food and culture you can find depending on where you choose to go.

Apulia/Basilicata Southern Coast to Coast

Duration: 7 Nights

Difficulty Level: 3-4

Tour Type: Self-Guided

Location: Trani

One of our quietest and most remote locations for bike tours in Italy, our Puglia/Basilicata Southern Coast to Coast self-guided road cycling tour is an ideal solution for those seeking a perfect cycling holiday and experience.  Taking you from eastern to western Italy, crossing “the boot” through Apulia and Basilicata, this road cycling tour is home to some of Italy’s finest caves and canyons. Visiting Matera, which itself is situated on two canyons carved by the Gravina River, this beautiful town is home to a complex of cave dwellings carved into an ancient canyon.

Later, you will cross valleys, climb the Apennines and reach the Pollino National Park, the largest natural area in Italy, before you finally arrive at Maratea, offering a breathtaking view of the Tyrrhenian Coast.

Pisa to Florence

Duration: 6 Nights

Difficulty Level: 3

Tour Type: Self-Guided

Location: Pisa

Home to some of Italy’s most beloved landscapes and across the birthplace of the Italian Renaissance, our self-guided “Giro of Tuscany” cycling holiday in Italy will take you from Pisa to Florence. This experience will offer hilly ranges, fertile plains and an abundance of art and culture. Starting off in Pisa, with its famous leaning tower, you will then head south, through Wine Country, experiencing a cacophony of local cuisine, famous wines, castles, cathedrals and world-famous town squares. .

An ideal combination of food, wine, historic attractions and beautiful sites, this cycling experience is perfect for those looking to balance relaxation and culture.


Bolzano to Venice

Duration: 7 nights

Difficulty Level: Level 3-4

Tour Type: Self-Guided

Location: Bolzano

One of our finest cycling holidays in Italy, our beautiful Bolzano to Venice self-guided cycling tour will transport you across the legendary mountains of the Dolomites all the way to the historical, world-famous floating city, Venice. Starting in Corvara, before descending down the hills of the Prosecco wine region this tour is best suited to experienced cyclists who are seeking a new challenge with incredible sights.


West Sicily

Duration: 7 nights

Difficulty Level: Level 2-3

Tour Type: Self-Guided

Location: Scopello

Starting in the charming village of Scopello,  home to an ancient hamlet, travelling across some of Sicily’s most stunning natural scenery, you will cycle through untouched countryside and vineyards, coastal saltpans and ancient ruins including the Doric Temple and Amphitheatre at Segesta.

Our West Sicily cycling tour offers wonderful opportunities to experience fantastic food, gorgeous wine and incredible ancient architecture and scenery, you will travel onwards to Mozia, then Marsala, where the many wine cellars play host to a wide menu of luxury wines. Then it’s on to Selinunte, home to historic sites and breathtaking temples in an ancient city, before you finally reach the village of Shicaccia, a beautiful coastal point to conclude your journey.


Via Francigena from Siena to Rome

Duration: 8 nights

Difficulty Level: Level 2-3

Tour Type: Self-Guided

Location: Siena

 A cycling holiday in Italy like no other; our Via Francigena from Siena to Rome tour offers an experience that will take you from the beautiful city of Siena, all the way to some of the world’s most breathtaking art, culture, history and iconography in Italy’s famous capital city, Rome. riding along the legendary dirt roads, you will cross the Val d’Arbia and the Val d’Orcia, both icons of the Tuscan landscape, you will pass through incredible villages like Bagno Vignoni, home to an enormous thermal pool, and Radicofani, a fortress that dominates southern Tuscany.

From there, you will visit the mediaeval centre of Viterbo, before reaching the heart of Rome, running along the river Tevere until you finally reach your final destination; St. Peter’s Square.


Venice to Porec

Duration: 7 Nights

Difficulty Level: Level 1-2

Tour Type: Self-Guided

Location: Venice (Mestre/Marghera)

Starting off in world-famous Venice, taking you all the way to the beautiful coastal Croatian town of Porec, our Venice to Porec cycling holiday in Italy is a gorgeous trip alongside the Italian Adriatic. Cycling past the beaches of holiday resorts of Jesolo and Caorle, there’s always an opportunity for a refreshing swim in the sea, while the inland regions of the Friuli-Venezia-Giulia offer medieval fortress towns, Roman archaeological excavations, Venetian architecture and delicious, traditional Italian Piazzas.

Finishing in the beautiful town of Porec on the Croatia peninsular, you can even choose to return to Venice by boat as an extra-special way to conclude your cycling holiday in Italy.

Tuscany to Umbria

Duration: 9 nights

Difficulty Level: Level 3 (3-4 if taking longer ride options)

Tour Type: Self-Guided

Location: Montepulciano

One of the most beautiful, explorative cycling holidays in Tuscany and across Italy, this tour will take you from Southern Tuscany to the heart of Umbria, two equally historic, cultural landmarks that are uniquely distinct from one another.  Southern Tuscany is the birthplace of the Italian language, the renaissance and the cradle of Italian art, known for its famous terracotta rooftops, hill towns and golden valleys. Umbria, meanwhile, is a holy land once historically bound to the Church-State, the land of St. Francis and the “Green Heart” of Italy, offering luscious green fields, plains, forests and meadows of the Apennine Mountains.

Our Tuscany to Umbria tour offers beautiful landscapes, historic art, culture and an exploration of two vastly different regions.

Turin to San Remo

Duration: 7 nights

Difficulty Level: Level 2

Tour Type: Self-Guided

Location: Turin

Heading from the Alps to the Sea, you begin in Turin, before cycling along quiet roads in a remarkably easy route. Recommended for beginners, as well as experienced cyclists, our Turin to San Remo cycling holiday in Italy offers fantastic views and enticing smells as you embrace the charming, rich culture as you luxuriate in some of Italy’s finest cuisine, culture and food.

South West Coast of Sardinia

Duration: 7 nights

Difficulty Level: Level 2

Tour Type: Self-Guided/Guided

Location: Near Oristano

A beautiful destination for both a guided and self-guided cycling tour in Italy, the Southwest Coast of Sardinia will transport you across the gorgeous coast of Sardinia, just south of the main body of the island into the Mediterranean. Home to fine beaches, forests that cling to the slopes of the predominately hilly landscape and a host of towns, temples and fortifications, first founded by Phoenicians and later occupied by Romans.

Starting in the Sinis peninsula, a luscious area of lagoons and abundant birdlife, you will travel southwest, reaching some of the coast’s finest beaches; Mari Emri and Is Aruta.

Hooked On Cycling – Cycling Tours In Tuscany and Across Italy

At Hooked on Cycling & Walking, we’re proud to offer the best range of cycling holidays in Italy and beyond, as well as walking holidays designed to suit everyone – whether you are a beginner looking to explore the outdoor world or an experienced cyclist or walker craving a challenge. The UK and Europe are home to some of the most beautiful locations in the world, Europe offers stunning landscapes and unparalleled history taking the traveller back centuries.

A self-guided holiday simply means that we organise all the important information you need such as routes and accommodation, but you have free reign while you’re on the trip without unnecessary interference. If you’re interested in cycling holidays in Tuscany and across Italy, book with us today.

About the author

I have worked for Hooked on Cycling & Walking since 2007 and love to travel and explore. I like to get outdoors and take my two young boys with me and hiking/cycling is enjoyed by all of us.

Leave a Reply