Cycling holidays are a brilliant way to take in breathtaking landscapes, soak up local culture, and stay active during the warm summer months of June to August. From picturesque countryside routes in the UK to alpine climbs and coastal trails across Europe, there’s something for every cyclist. For those after more adventure, South America and Asia also offer unforgettable rides. With long days and fine weather, summer is the perfect time for a cycling getaway.
.png)
Destinations (81)
Types of Cycling / Grades (7)
Departure Month
Level of Support
Destinations (81)
Types of Cycling / Grades (7)
Departure Month
Level of Support
Page 3 of 6
Select Order
Order By
Guided
Grand Traverse Classic - North to South
Guided Road Cycling Holiday
| Start Date | End Date | Price p.p. |
|---|---|---|
| 25/09/2025 Last Spaces | 11/10/2025 | £4,395.00 |
| 21/05/2026 | 06/06/2026 | £4,615.00 |
| 24/09/2026 | 10/10/2026 | £4,615.00 |
- 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!
Self-Guided
Classic Tuscany
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. You may choose to hire an e-bike on a group or supported tour but bear in mind that the pace will be set to riders without an e-bike.
| Start Date | End Date | Price p.p. |
|---|---|---|
| 28/09/2025 | 04/10/2025 | £1,195.00 |
Daily departures available. The season prices below are per person and are applicable for all start dates between and inclusive of the stated dates.
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
Alternatively for a great value holiday, please select one of our scheduled departures below.
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
Guided
Tuscany - Sacred Routes
Guided Mountain Bike Holiday
E-MTB HIRE AVAILABLE
This holiday is great fun on a regular mountain bike or an e-mountain bike and you can choose to hire either when you book your holiday with us! If you’re an experienced rider, you can choose one of our quality e-mountain hire bikes and experience the buzz of a pedal-assisted ride. Select your e-MTB hire when you book a holiday with us. Bear in mind that the pace will be set to riders with a regular mountain bike.
| Start Date | End Date | Price p.p. |
|---|---|---|
| 06/09/2025 | 12/09/2025 | £2,065.00 |
| 16/05/2026 | 22/05/2026 | £2,175.00 |
| 05/09/2026 | 11/09/2026 | £2,175.00 |
- 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
Guided
Dolomiti Discoverer
Guided Road Cycling Holiday
| Start Date | End Date | Price p.p. |
|---|---|---|
| 04/07/2026 | 11/07/2026 | £2,625.00 |
| 18/07/2026 | 25/07/2026 | £2,625.00 |
- 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!
Self-Guided
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 – £1695 24 Mar – 16 Jun and 03 Sep – 29 Oct
Season 2 – £1865 17 Jun – 30 Jun and 01 – 02 Sep
2026 29 Mar – 26 Oct (excluding dates throughout July and August)
Season 1 – £1785 29 Mar – 14 Jun and 09 Sep – 26 Oct
Season 2 – £1965 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.
- 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
Self-Guided
Puglia
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.
| Start Date | End Date | Price p.p. |
|---|---|---|
| 29/09/2025 | 06/10/2025 | £1,285.00 |
Daily departures available. The season prices below are per person and are applicable for all start dates between and inclusive of the stated dates.
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
Alternatively for a great value holiday select one of our scheduled departures below.
- 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
Guided
Puglia
Guided Leisure Cycling Holiday
OPTIONAL E-BIKE DEPARTURES
We offer this holiday with an e-bike only departure as well as regular trips where you can choose a regular bike or a pedal assist e-bike hire. Our e-bike only departures allow you to experience more on two wheels whilst riding with like-minded Skedaddlers. Confident cyclists will enjoy the boost from a battery for those cheeky climbs and longer distances. With less effort required on the bike, you’ll have more energy at the end of the day for off-the-bike activities. Remember to select your e-bike hire when you book your holiday with us. You may choose to hire an e-bike on a regular trip but bear in mind that the pace will be set to riders without an e-bike.
| Start Date | End Date | Price p.p. |
|---|---|---|
| 20/09/2025 Guaranteed | 27/09/2025 | £2,095.00 |
| 07/06/2026 | 14/06/2026 | £2,195.00 |
| 20/09/2026 | 27/09/2026 | £2,195.00 |
- Cycling through wonderful landscapes of ancient olive groves, vineyards and stunning coastlines
- Exploring the UNESCO World Heritage town of Alberobello and the Baroque city of Lecce
- Discovering the traditional Trulli houses of Puglia
- Relaxing each night in comfortable 3 and 4* hotels in authentic Apulian towns and villages
- Stopping at beautiful sandy beaches with turquoise seas
- Tasting delicious Apulian produce, like orecchiette and extra virgin olive oil
Bike and Boat
Venetian Waterways (Mantova to Venice)
Bike and Barge 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.
| Start Date | End Date | Price p.p. |
|---|---|---|
| 12/07/2025 Ave Maria Fully Booked | 19/07/2025 | £2,025.00 |
| 19/07/2025 Vita Pugna Contact Us | 26/07/2025 | £1,625.00 |
| 26/07/2025 Ave Maria Contact Us | 02/08/2025 | £2,025.00 |
| 02/08/2025 Vita Pugna Fully Booked | 09/08/2025 | £1,625.00 |
| 09/08/2025 Ave Maria Fully Booked | 16/08/2025 | £2,025.00 |
| 16/08/2025 Vita Pugna Fully Booked | 23/08/2025 | £1,625.00 |
| 23/08/2025 Ave Maria | 30/08/2025 | £2,425.00 |
| 30/08/2025 Vita Pugna Fully Booked | 06/09/2025 | £1,885.00 |
| 06/09/2025 Ave Maria Fully Booked | 13/09/2025 | £2,425.00 |
| 13/09/2025 Vita Pugna Fully Booked | 20/09/2025 | £1,885.00 |
| 20/09/2025 Ave Maria Fully Booked | 27/09/2025 | £2,425.00 |
| 27/09/2025 Vita Pugna Fully Booked | 04/10/2025 | £1,885.00 |
| 04/10/2025 Ave Maria | 11/10/2025 | £2,425.00 |
| 11/10/2025 Vita Pugna Fully Booked | 18/10/2025 | £1,885.00 |
| 18/10/2025 Ave Maria | 25/10/2025 | £2,225.00 |
| 21/03/2026 Ave Maria | 28/03/2026 | £1,395.00 |
| 28/03/2026 Vita Pugna | 04/04/2026 | £1,165.00 |
| 04/04/2026 Ave Maria | 11/04/2026 | £2,225.00 |
| 11/04/2026 Vita Pugna | 18/04/2026 | £1,755.00 |
| 18/04/2026 Ave Maria | 25/04/2026 | £2,225.00 |
| 25/04/2026 Vita Pugna | 02/05/2026 | £1,755.00 |
| 02/05/2026 Ave Maria | 09/05/2026 | £2,455.00 |
| 09/05/2026 Vita Pugna | 16/05/2026 | £1,885.00 |
| 16/05/2026 Ave Maria | 23/05/2026 | £2,455.00 |
| 23/05/2026 Vita Pugna | 30/05/2026 | £1,885.00 |
| 30/05/2026 Ave Maria | 06/06/2026 | £2,225.00 |
| 06/06/2026 Vita Pugna | 13/06/2026 | £1,755.00 |
| 13/06/2026 Ave Maria | 20/06/2026 | £2,225.00 |
| 20/06/2026 Vita Pugna | 27/06/2026 | £1,755.00 |
| 27/06/2026 Ave Maria | 04/07/2026 | £1,855.00 |
| 04/07/2026 Vita Pugna | 11/07/2026 | £1,635.00 |
| 11/07/2026 Ave Maria | 18/07/2026 | £1,855.00 |
| 18/07/2026 Vita Pugna | 25/07/2026 | £1,635.00 |
| 25/07/2026 Ave Maria | 01/08/2026 | £1,855.00 |
| 01/08/2026 Vita Pugna | 08/08/2026 | £1,635.00 |
| 08/08/2026 Ave Maria | 15/08/2026 | £1,855.00 |
| 15/08/2026 Vita Pugna | 22/08/2026 | £1,635.00 |
| 22/08/2026 Ave Maria | 29/08/2026 | £1,855.00 |
| 29/08/2026 Vita Pugna | 05/09/2026 | £1,995.00 |
| 05/09/2026 Ave Maria | 12/09/2026 | £2,595.00 |
| 12/09/2026 Vita Pugna | 19/09/2026 | £1,995.00 |
| 19/09/2026 Ave Maria | 26/09/2026 | £2,595.00 |
| 26/09/2026 Vita Pugna | 03/10/2026 | £1,995.00 |
| 03/10/2026 Ave Maria | 10/10/2026 | £2,595.00 |
| 10/10/2026 Vita Pugna | 17/10/2026 | £1,995.00 |
| 17/10/2026 Ave Maria | 24/10/2026 | £2,225.00 |
- Cycling through some of Northern Italy’s most enticing cities
- Staying on board the modern, bright and spacious Ave Maria or the traditional Vita Pugna
- Spending the day discovering Mantova
- Riding alongside the River Po, the longest river in Italy
- Experiencing the Po Delta, one of Europe’s largest wetlands
- Finishing your trip in beautiful Venice
Bike and Boat
Venetian Waterways (Venice to Mantova)
Bike and Barge 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
| Start Date | End Date | Price p.p. |
|---|---|---|
| 12/07/2025 Vita Pugna Fully Booked | 19/07/2025 | £1,625.00 |
| 19/07/2025 Ave Maria Guaranteed | 26/07/2025 | £2,025.00 |
| 26/07/2025 Vita Pugna Fully Booked | 02/08/2025 | £1,625.00 |
| 02/08/2025 Ave Maria Fully Booked | 09/08/2025 | £2,025.00 |
| 09/08/2025 Vita Pugna Fully Booked | 16/08/2025 | £1,625.00 |
| 16/08/2025 Ave Maria | 23/08/2025 | £2,025.00 |
| 23/08/2025 Vita Pugna Fully Booked | 30/08/2025 | £1,885.00 |
| 30/08/2025 Ave Maria | 06/09/2025 | £2,425.00 |
| 06/09/2025 Vita Pugna Fully Booked | 13/09/2025 | £1,885.00 |
| 13/09/2025 Ave Maria Fully Booked | 20/09/2025 | £2,425.00 |
| 20/09/2025 Vita Pugna Fully Booked | 27/09/2025 | £1,885.00 |
| 27/09/2025 Ave Maria Fully Booked | 04/10/2025 | £2,425.00 |
| 04/10/2025 Vita Pugna Fully Booked | 11/10/2025 | £1,885.00 |
| 11/10/2025 Ave Maria | 18/10/2025 | £2,425.00 |
| 18/10/2025 Vita Pugna | 25/10/2025 | £1,745.00 |
| 25/10/2025 Ave Maria | 01/11/2025 | £2,225.00 |
| 28/03/2026 Ave Maria | 04/04/2026 | £1,395.00 |
| 04/04/2026 Vita Pugna | 11/04/2026 | £1,755.00 |
| 11/04/2026 Ave Maria | 18/04/2026 | £2,225.00 |
| 18/04/2026 Vita Pugna | 25/04/2026 | £1,755.00 |
| 25/04/2026 Ave Maria | 02/05/2026 | £2,225.00 |
| 02/05/2026 Vita Pugna | 09/05/2026 | £1,885.00 |
| 09/05/2026 Ave Maria | 16/05/2026 | £2,455.00 |
| 16/05/2026 Vita Pugna | 23/05/2026 | £1,885.00 |
| 23/05/2026 Ave Maria | 30/05/2026 | £2,455.00 |
| 30/05/2026 Vita Pugna | 06/06/2026 | £1,755.00 |
| 06/06/2026 Ave Maria | 13/06/2026 | £2,225.00 |
| 13/06/2026 Vita Pugna | 20/06/2026 | £1,755.00 |
| 20/06/2026 Ave Maria | 27/06/2026 | £2,225.00 |
| 27/06/2026 Vita Pugna | 04/07/2026 | £1,635.00 |
| 04/07/2026 Ave Maria | 11/07/2026 | £1,855.00 |
| 11/07/2026 Vita Pugna | 18/07/2026 | £1,635.00 |
| 18/07/2026 Ave Maria | 25/07/2026 | £1,855.00 |
| 25/07/2026 Vita Pugna | 01/08/2026 | £1,635.00 |
| 01/08/2026 Ave Maria | 08/08/2026 | £1,855.00 |
| 08/08/2026 Vita Pugna | 15/08/2026 | £1,635.00 |
| 15/08/2026 Ave Maria | 22/08/2026 | £1,855.00 |
| 22/08/2026 Vita Pugna | 29/08/2026 | £1,635.00 |
| 29/08/2026 Ave Maria | 05/09/2026 | £2,595.00 |
| 05/09/2026 Vita Pugna | 12/09/2026 | £1,995.00 |
| 12/09/2026 Ave Maria | 19/09/2026 | £2,595.00 |
| 19/09/2026 Vita Pugna | 26/09/2026 | £1,995.00 |
| 26/09/2026 Ave Maria | 03/10/2026 | £2,595.00 |
| 03/10/2026 Vita Pugna | 10/10/2026 | £1,995.00 |
| 10/10/2026 Ave Maria | 17/10/2026 | £2,595.00 |
| 17/10/2026 Vita Pugna | 24/10/2026 | £1,755.00 |
| 24/10/2026 Ave Maria | 31/10/2026 | £2,225.00 |
- Cycling through some of Northern Italy’s most enticing cities
- Staying on board the modern, bright and spacious Ave Maria or the traditional Vita Pugna
- Exploring the beautiful city of Venice
- Riding alongside the River Po, the longest river in Italy
- Experiencing the Po Delta, one of Europe’s largest wetlands
- Spending the day discovering Mantova
Self-Guided
Tuscany - Pisa to Florence
Self-Guided Leisure Cycling Holiday
| Start Date | End Date | Price p.p. |
|---|---|---|
| 16/09/2025 Guaranteed | 23/09/2025 | £1,175.00 |
Daily departures available. The season prices below are per person and are applicable for all start dates between and inclusive of the stated dates.
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 – £1485 17 – 30 Jun and 01 – 02 Sep
2026 29 Mar – 26 Oct (excluding dates throughout July and August)
Season 1 – £1365 29 Mar – 14 Jun and 09 Sep – 26 Oct
Season 2 – £1565 15 – 30 Jun and 01 – 08 Sep
Alternatively for a great value holiday select one of our scheduled departures below.
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
Not sure which trip's right for you? Just ask!
Get in touch and we'll help you find your perfect trip.
News, Reviews & Stories
The Lowdown on Mountain Biking in the Spanish Pyrenees
What makes the Pyrenees one of Europe's best mountain biking destinations...
2025 trends to watch
To help you plan, we wanted to look at some of the trends we believe will go the extra mile...