Book your Fall escape with Skedaddle! We’ve curated a list of our most popular guided small-group road bike tours - the perfect way to extend your summer of cycling. Don’t miss the opportunity to ride through breathtaking landscapes with our expert guides! Need more convincing or have questions? Check out What Our Holidays Include here.
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Destinations (72)
Types of Cycling / Grades (1)
Departure Month
Level of Support
Destinations (72)
Types of Cycling / Grades (1)
Departure Month
Level of Support
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Guided
NEW! Coast to Coast - Puglia to Cilento
Guided Road Bike Tour
| Start Date | End Date | Price p.p. |
|---|---|---|
| 28/09/2025 Guaranteed | 05/10/2025 | $2,850.00 |
| 06/10/2025 Guaranteed | 13/10/2025 | $2,850.00 |
- An epic coast to coast journey through southern Italy riding from the Adriatic coast to the Tyrrhenian Sea
- Exploring the UNESCO World Heritage sites of Alberobello, Matera, Padula and Paestum
- Losing ourselves in the labyrinthic white washed alleyways of Noci and Tricarico
- Climbing the hills of little-known Basilicata, to the hill-top villages of Castelmezzano, Calvello and Marsico Vetere
- Cycling through the Dolomiti Lucane, southern Italy’s lesser-known Dolomites
- Enjoying the roller-coaster ride along the Cilento Coast from Palinuro to Paestum
- Sampling southern Italy’s best food and wine
Guided
Coast to Coast - L'Adriatico al Tirreno
Guided Road Bike Tour
| Start Date | End Date | Price p.p. |
|---|---|---|
| 13/09/2025 Guaranteed | 21/09/2025 | $3,665.00 |
- An epic coast to coast journey riding all the way from the Adriatic coast to the Tyrrhenian Sea
- Cycling through the smallest republic in Europe, San Marino
- Easing along the rolling Nove Colli hills, the routes of the famous Italian Gran Fondo
- Visiting historical sites such as the Palazzo Ducale in Orvieto and San Francis Abbey in Assisi
- Staying in quality accommodation, with fantastically warm hospitality
- Riding to Gubbio and Assisi, UNESCO World Heritage sites
Guided
Eden Valley and the North Pennines
Guided Road Bike Tour
| Start Date | End Date | Price p.p. |
|---|---|---|
| 14/09/2025 Guaranteed | 19/09/2025 | $1,525.00 |
| 26/07/2026 | 31/07/2026 | $1,600.00 |
| 20/09/2026 | 25/09/2026 | $1,600.00 |
- Admiring the rugged natural beauty of the North Pennines
- Riding up to the top of Hartside – a Tour of Britain favourite – from both directions
- Miles and miles of quiet picturesque valleys and dramatic moorland
- Pedalling up to Alston, the ‘joint highest market town’ in England
- Cycling through the Howgill Fells, perfectly situated between the Lake District and Yorkshire Dales National Parks
- Enjoying a well deserved pint of Pennine Pale Ale at the end of a day in the saddle
Guided
Corsica - Southern Secrets
Guided Road Bike Tour
| Start Date | End Date | Price p.p. |
|---|---|---|
| 20/09/2025 | 27/09/2025 | $3,425.00 |
- Approaching Corte’s towering citadel at the end of our first day’s ride
- Exploring Corsican mountain villages, distinct from anywhere else in France
- Descending sweeping roads which carve through cool pine forests
- Bonifacio’s dramatic cliff top old town
- Earning the rewarding views over the Med after a challenging climb
- Fuelling up with the delicious local produce
Guided
Basque Country to Andalucia Explorer - North to South
Guided Road Bike Tour
| Start Date | End Date | Price p.p. |
|---|---|---|
| * 31/08/2025 Last Spaces | 20/09/2025 | $7,420.00 |
- Starting in style with a Pintxos tour in elegant San Sebastian
- Cycling through the vineyards & dramatic mountains of Rioja
- Spending an evening in the Monastery of Valvanera
- Seduced by Segovia with its castle and cathedral
- Descending from the Sierras to the charming beauty of Cordoba
- Finishing your ride in style at the fun loving city of Malaga-
Guided
St Malo to Nice Classic
Guided Road Bike Tour
| Start Date | End Date | Price p.p. |
|---|---|---|
| 06/09/2025 Guaranteed | 20/09/2025 | $5,995.00 |
| 12/06/2026 | 26/06/2026 | $6,280.00 |
| 04/09/2026 | 18/09/2026 | $6,280.00 |
- Cycling along the Brittany coast with views out to the Abbey of Mont St Michel
- Travelling under your own power all the way from the Channel to the Mediterranean
- Following riverside roads along the Loire, Dordogne and the Rhône
- Riding through the wine drenched Châteauneuf-du-Pape!
- Riding through the lavender fields of Provence and winding your way through the Verdon Gorge
- Descending to Nice to ride along the Promenade des Anglais like a Tour de France winner!
Guided
Sardinia - Coastal Explorer
Guided Road Bike Tour
| Start Date | End Date | Price p.p. |
|---|---|---|
| 06/09/2025 | 13/09/2025 | $2,710.00 |
| 20/09/2025 Last Spaces | 27/09/2025 | $2,710.00 |
| 04/10/2025 Guaranteed | 11/10/2025 | $2,710.00 |
- Riding the stunning coastal road from Alghero to Bosa
- The ride to Montiferru through its oak forest
- Sampling delightful Sardinian foods with a vast variety of local wines
- Enjoying the view of Pan di Zucchero on the Nebida coastal ride
- Sweeping down the long descent to Fluminimaggiore and Masua
- Glimpsing the white beaches which hug the south west coast road
Guided
Grand Traverse Classic - North to South
Guided Road Bike Tour
| Start Date | End Date | Price p.p. |
|---|---|---|
| 25/09/2025 Last Spaces | 11/10/2025 | $6,280.00 |
| 21/05/2026 | 06/06/2026 | $6,595.00 |
| 24/09/2026 | 10/10/2026 | $6,595.00 |
- 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!
Guided
Basque Country to Andalucia Classic - North to South
Guided Road Bike Tour
| Start Date | End Date | Price p.p. |
|---|---|---|
| 28/09/2025 Last Spaces | 13/10/2025 | $5,905.00 |
- Cycling through the varied beauty of 14 national parks
- Delicious regional dishes which change from day to day as you traverse the entire country
- Crossing the granite Guadarrama and Gredos mountain ranges as you move from the north to the south of the country
- Views over the Straits of Gibraltar to Morocco
- The beautiful towns of San Sebastian, Guadaloupe and Ronda
- The satisfaction of arriving in to Tarifa with over 1,000 miles of Spanish roads having passed beneath your wheels
Guided
Sierra Nevada and Granada
Guided Road Bike Tour
| Start Date | End Date | Price p.p. |
|---|---|---|
| 12/10/2025 Guaranteed | 18/10/2025 | $2,695.00 |
- Checking out the white mountain villages of the Alpujarras
- A night in a luxurious cave house in Guadix
- The Sierra Nevada Challenge – riding to the roof of Spain
- The classic Vuelta ride through the Sierra de Pandera
- Tasty tapas and sunset sangrias
- The descent to Granada and its amazing Alhambra Palace
Not sure which trip's right for you? Just ask!
Get in touch and we'll help you find your perfect trip.
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