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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Sardinia - Island Flavours
Self-Guided Leisure 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 – £1545 24 Mar – 08 Jun / 09 Sep – 29 Oct
Season 2 – £1675 01 Sept – 08 Sept
- Checking out the UNESCO heritage site of Barumini Nuraghe
- Enjoying the long descent to Fluminimaggiore and Masua
- Riding along the Nebida coastline and marvelling at the view of Pan di Zucchero
- Sampling local specialities at Carloforte, on St Pietro island
- Experiencing the friendliness and hospitality of the Sardinian people
- Discovering the white beaches along the south-west coastal road
Sardinia - Coast to Coast
Self-Guided Mountain Bike 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 – £1525 24 Mar – 08 Jun / 09 Sep – 29 Oct
Season 2 – £1675 01 Sept – 08 Sept
- Experiencing the friendliness of the Sardinian people
- Piscinas Beach – The highest sand dunes in the Med.
- Checking out the UNESCO heritage Nuraghe of Barumini
- Riding varied biking trails in real remote mountain areas
- Good home cooked food, washed down with local wine
- The stunning descent to Bari Sardo on the East Coast
Sardinia - Coast to Coast
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 – £1525 24 Mar – 08 Jun / 09 Sep – 29 Oct
Season 2 – £1675 01 Sept – 08 Sept
- 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 Sardinia
- Cycling through the Sardinian “Blue Zone”
- Dining on delicious home cooked food, washed down with tasty local wine!
- The stunning descent to Bari Sardo on the East Coast
Sardinia - Coastal Explorer
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 – £1465 24 Mar – 08 Jun and 09 Sep – 29 Oct
Season 2 – £1685 01 Sept – 08 Sept
SAVE ON 2025 EARLY SEASON ESCAPES!
Book your early cycling escape before the 17th of November and save £75. 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
Tuscany - Giro della Toscana
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 throughout July and August)
Season 1 – £1675 24 Mar – 16 Jun and 03 Sep – 29 Oct
Season 2 – £1925 17 Jun – 30 Jun and 01 – 02 Sep
- 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
Lake Garda to Venice
Self-Guided Leisure Cycling Holiday
E-BIKE HIRE AVAILABLE
This tour 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 (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
If you‘re looking for a longer holiday, our Via Claudia 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!
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
Classic Tuscany
Self-Guided Leisure 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 throughout July and August)
Season 1 – £1335 24 Mar – 16 Jun and 03 Sep – 29 Oct
Season 2 – £1575 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.
- Staying at Tuscan farms overlooking stunning countryside
- Visiting the famous towns of Monteriggioni, Radda in Chianti and Siena
- Riding through wonderful landscapes, wide open fields, cypress-lined hills and vineyards
- Trying delicious, regional dishes
- Sampling the best wines of Chianti, Montepulciano and Montalcino
- Absorbing the atmosphere of San Gimignano – a UNESCO World Heritage Site
Tuscany - Sacred Routes
Self-Guided Mountain Bike 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 – £1575 24 Mar – 16 Jun and 03 Sep – 29 Oct
Season 2 – £1715 17 Jun – 30 Jun and 01 – 02 Sept
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.
- Staying in lovely Tuscan accommodation overlooking stunning landscapes
- Riding the Montagnola trails, the location of a well-known Sienese MTB race
- Sampling the best wines of Chianti, Montepulciano and Montalcino
- Riding down the “Crete Senesi” on a roller coaster ridge ride
- Enjoying the journey across Tuscany on a variety of terrain
- Visiting the famous hilltop towns of San Gimignano, Monteriggioni, San Quirico d‘Orcia and Pienza
Puglia
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 are applicable for all start dates between and inclusive of the stated dates.
2025 24 Mar – 29 Oct (excluding departures from 09 Jun to 31 Aug)
Season 1 – £1495 24 Mar – 08 Jun / 09 Sep – 29 Oct
Season 2 – £1675 01 Sept – 08 Sept
- Cycling through lush landscapes of ancient olive groves and vineyards
- Exploring the UNESCO World Heritage town of Alberobello
- Discovering the traditional Trulli houses of Puglia
- Relaxing each evening in comfortable hotels in authentic towns and villages
- Stopping at beautiful, sandy beaches with turquoise seas
- Tasting delicious local products, like extra virgin olive oil and Primitivo wine
Tuscany - Pisa to Florence
Self-Guided Leisure 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 throughout July and August)
Season 1 – £1295 24 Mar – 16 Jun and 03 Sep – 29 Oct
Season 2 – £1465 17 – 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.
- Riding between two of Italy’s most iconic cities
- Exploring Pisa, home of the world-famous Piazza dei Miracoli
- Cycling along quiet country lanes through Tuscan countryside
- Cycling past fairy tale Renaissance palaces and villas
- Visiting Vinci, the birthplace of Leonardo da Vinci
- Spending a free day in Florence, the birthplace of the Renaissance
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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.
News, Reviews & Stories
Cycling the Vineyards of La Rioja
A famed wine region with world heritage sites, medieval villages, and dramatic views - a true connoisseur's dream.