Italy, with its diverse landscapes and rich cultural heritage, is a cyclist's paradise. Saddle Skedaddle's self-guided cycling holidays offer the perfect way to explore this beautiful country at your own pace. Whether you're riding through Tuscany's vineyards, exploring the stunning southern region of Puglia, or around the serene Lake Garda, our expertly crafted routes ensure an unforgettable experience. Italy has so much to offer covering self-guided mountain biking, road cycling as well as some exciting gravel trips such as the Strade Bianche Explorer. Or if you would prefer to do things at a more relaxed pace and take in the scenery our leisure holidays give you the chance to soak it all in. We take care of all the details, from handpicked accommodations to luggage transfers, allowing you to fully immerse yourself in Italy's charm. Read more on our guided and self-guided options so you can find the right holiday for you.
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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.
2025 24 Mar – 29 Oct (excluding dates from 09 Jun – 31 Aug)
Season 1 – £1695 24 Mar – 08 Jun / 09 Sep – 29 Oct
Season 2 – £1855 01 Sept – 08 Sept
2026 29 Mar – 26 Oct (excluding dates from 08 Jun – 31 Aug)
Season 1 – £1795 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
La Via Claudia
Self-Guided Leisure Cycling Holiday
E-BIKE HIRE AVAILABLE
This holiday is well-suited to both regular bikes and pedal assist e-bikes, and you can choose to hire either when you book your holiday with us. Confident cyclists will enjoy the boost from a battery for those cheeky climbs, and with less effort required on the bike, you’ll have more energy at the end of the day for off-the-bike activities.
Daily departures available. The season prices below are per person and are applicable for all start dates between and inclusive of the stated dates.
2025 21 Apr – 29 Oct
Season 1 – £1945 21 Apr – 16 Jun and 03 Sep – 29 Oct
Season 2 – £2135 17 Jun – 02 Sep
2026 21 Apr – 29 Oct
Season 1 – £2045 18 Apr – 14 Jun and 09 Sep – 26 Oct
Season 2 – £2245 15 Jun – 08 Sep
If you‘re looking for a longer holiday, our Lake Garda to Venice route links into this tour perfectly; two self-guided tours of a similar grade that you‘re able to do back to back. Contact us if you’d like more info on this!
- Starting your week at the picturesque Lake Resia, admiring the bell tower peeking through the waves
- Cycling beside the vivid blue waters of the River Etsch
- Absorbing the history of an ancient trade route, all by bike
- Exploring Merano – The Jewel of South Tyrol
- Wine tasting in Caldaro, part of the Strade del Vino
- Enjoying an apperitivo in Piazza Arena in Verona
Sicily
Self-Guided Leisure Cycling Holiday
E-BIKE HIRE AVAILABLE
This holiday is well-suited to both normal bikes and pedal assist e-bikes and you can choose to hire either when you book your holiday with us. Confident cyclists will enjoy the boost from a battery for those cheeky climbs, and with less effort required on the bike, you’ll have more energy at the end of the day for off-the-bike activities.
Daily departures available. The season prices below are per person, and applicable for all start dates between and inclusive of the stated dates.
2025 24 Mar – 29 Oct (excluding departures from 09 Jun – 31 August)
Season 1 – £1675 24 Mar – 08 Jun and 09 Sep – 29 Oct
Season 2 – £1895 01 Sep – 08 Sep
2026 29 Mar – 26 Oct (excluding departures from 08 Jun – 31 August)
Season 1 – £1765 29 Mar – 07 Jun and 09 Sep – 26 Oct
Season 2 – £1995 01 Sep – 08 Sep
- Visiting the Baroque towns of Modica, Ragusa and Noto, all UNESCO Heritage Sites
- Sampling delicious Sicilian pastries, like cannoli
- Cycling along the beautiful coastal road to Capo Passero
- Exploring the medieval streets of Ortigia di Siracusa
- Enjoying an aperitivo ‘al fresco’ with the locals in one of the many piazzas
- Discovering the astonishing Oasis of Vendicari
Emilia-Romagna - The Food Valley
Self-Guided Leisure Cycling Holiday
E-BIKE HIRE AVAILABLE
This holiday is well-suited to both regular bikes and pedal assist e-bikes, and you can choose to hire either when you book your tour with us. Confident cyclists will enjoy the boost from a battery for those cheeky climbs, and with less effort required on the bike, you’ll have more energy at the end of the day for off-the-bike activities.
Daily departures. The season prices below are per person and are applicable for all start dates between and inclusive of the stated dates.
2025 24 Mar – 29 Oct (excluding dates throughout July and August)
Season 1 – £1495 24 Mar – 16 Jun and 03 Sep – 29 Oct
Season 2 – £1645 17 Jun – 30 Jun and 01 – 02 Sep
2026 29 Mar – 26 Oct (excluding dates throughout July and August)
Season 1 – £1575 29 Mar – 14 Jun and 09 Sep – 26 Oct
Season 2 – £1735 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.
- Gently cycling on quiet roads and cycle paths through beautiful countryside
- Sampling tasty slow-food produce on the Food Valley Bike route from Cremona to Parma
- Tasting authentic Italian food in their towns of origin such as Parma Ham, Parmigiano Reggiano, Balsamic Vinegar, and Bolognese Ragù
- Visiting the hometown of the famous Italian composer Giuseppe Verdi
- Exploring modern and bustling Modena
- Taking in the vibrant university city of Bologna
Prosecco To The Sea
Self-Guided Leisure Cycling Holiday
E-BIKE HIRE AVAILABLE
This holiday is well-suited to both regular bikes and pedal assist e-bikes, and you can choose to hire either when you book your tour with us. Confident cyclists will enjoy the boost from a battery for those cheeky climbs, and with less effort required on the bike, you’ll have more energy at the end of the day for off-the-bike activities.
Daily departures available. The season prices below are per person, and are applicable for all start dates between and inclusive of the stated dates.
2025 21 Apr – 29 Oct (no departures in July and August)
Season 1 – £1135 21 Apr – 16 Jun and 03 Sep – 29 Oct
Season 2 – £1195 17 Jun – 30 Jun and 01 – 02 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.
- 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 served on terraces overlooking vineyards
- Pretty medieval towns and historic castles
- Riding close to Venice Lagoon
- Dipping your toes in the Adriatic sea
Italy
Lake Garda to Venice
Self-Guided Family Cycling Holiday
Duration
8 daysPrices from
£1,775 P.P.Lake Garda to Venice
Self-Guided Family 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.
2025 21 Apr – 29 Oct (excluding dates throughout July and August)
Season 1 – £1775 21 Apr – 16 Jun and 03 Sep – 29 Oct
Season 2 – £1995 17 Jun – 30 Jun and 01 – 02 Sep
2026 18 Apr – 26 Oct (excluding dates throughout July and August)
Season 1 – £1865 18 Apr – 14 Jun and 09 Sep – 26 Oct
Season 2 – £2095 15 Jun – 30 Jun and 01 – 08 Sep
We can offer the following discounts for children under 18:
We can offer a 20% discount for any child under 18 travelling with 2 fully-paying passengers. If you’re happy to share a family room (where available) we can often offer an additional 10% – please chat to our team about your preferred rooming arrangements.
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.
- Enjoying a swim in Lake Garda
- Cycling along Pellestrina Island surrounded by Venetian lagoons and fishing boats
- Absorbing the hidden Rennaisance gems of the ‘belpaese’
- Exploring Verona – a piece of art in itself
- Discovering the medieval fortification of Montagnana
- Taking a gondola ride along the canals of Venice
Italy
Strade Bianche Explorer
Self-Guided Gravel Riding Holiday
Duration
8 daysPrices from
£1,735 P.P.Strade Bianche Explorer
Self-Guided Gravel Riding 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.
2025 24 Mar – 29 Oct (excluding dates throughout July and August)
Season 1 – £1735 24 Mar – 16 Jun and 03 Sep – 29 Oct
Season 2 – £1945 17 Jun – 30 Jun and 01 – 02 Sep
2026 29 Mar – 26 Oct (excluding dates throughout July and August)
Season 1 – £1825 29 Mar – 14 Jun and 09 Sep – 26 Oct
Season 2 – £2045 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.
- Riding some of the classic “Strade Bianche” of Tuscany as well as lesser-known gravel routes
- Cycling through the historic wine regions of Tuscany, stopping off for a bit of wine tasting
- Exploring the region on a mix of terrains
- Riding the stunning UNESCO heritage region of Val d’Orcia
- Relaxing in small villages for a coffee with the locals
- Easing along the rolling hills of the ‘Colli Senesi’
- Chilling out with a post-ride Chianti or Brunello
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Italy is a destination that captivates the senses and ignites the imagination, making it the perfect place for a cycling holiday. From its rolling hills and sun-soaked vineyards to its rugged coastlines and historic cities, Italy offers a diverse tapestry of landscapes that are ideal for exploration on two wheels. Cycling through Italy allows you to experience the country’s rich cultural heritage up close, every region in Italy has its own unique character and charm, with vibrant local traditions, world-renowned cuisine, and stunning natural beauty.
At Saddle Skedaddle, our self-guided cycling holidays are designed to help you discover the very best of Italy at your own pace. Whether you’re winding through the olive groves and whitewashed villages of Puglia, traversing across Sardinia, or leisurely exploring the picturesque shores of Lake Garda, each route offers a carefully curated mix of well-known highlights and hidden gems. We ensure that every detail is taken care of, from handpicked accommodations that reflect the local flavour to seamless luggage transfers, allowing you to focus entirely on enjoying your ride.
What sets our self-guided tours apart is the freedom they offer combined with the security of knowing you’re fully supported. With detailed route notes, GPS files, and 24/7 local assistance, you can cycle confidently through Italy’s stunning landscapes, pausing to savour a glass of Chianti in Tuscany or indulgent cuisine from the Emilia Romagna region, the home of some of Italy’s most beloved foods. Our commitment to sustainable travel and authentic experiences means that you’ll connect deeply with the places you visit, whether through a stay in a family-run agriturismo or a visit to a traditional artisan workshop.
Italy is more than just a destination; it’s a journey through history, culture, and natural beauty. With Saddle Skedaddle, that journey becomes an unforgettable cycling adventure, tailored to your interests and pace.
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