Book your Fall escape with Skedaddle! We’ve curated a list of our most popular guided small-group cycling 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 (7)
Departure Month
Level of Support
Destinations (72)
Types of Cycling / Grades (7)
Departure Month
Level of Support
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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
Guided
The Andes and the Lake District
Guided Road Bike Tour
| Start Date | End Date | Price p.p. |
|---|---|---|
| 25/10/2025 Guaranteed | 06/11/2025 | $5,565.00 |
| 21/02/2026 | 05/03/2026 | $5,565.00 |
| 24/10/2026 | 05/11/2026 | $5,895.00 |
| 13/03/2027 | 25/03/2027 | $5,895.00 |
- Your first glimpse of the snowcapped Volcan Osorno
- Crossing over the Andes not just once but twice!
- Cycling the Seven Lakes Route from San Martin to Villa Angostura
- Quiet roads and the backdrop of the awesome Andes
- The immense monkey puzzle trees around Villa Pehuenia
- Relaxing in the Puyehue hot springs
- Tasting all the culinary delights of the region
Guided
Classic Kerala
Guided Bike Tour
| Start Date | End Date | Price p.p. |
|---|---|---|
| 01/11/2025 Fully Booked | 14/11/2025 | $3,425.00 |
| 22/11/2025 Fully Booked | 05/12/2025 | $3,425.00 |
| 01/02/2026 | 14/02/2026 | $3,350.00 |
| 21/11/2026 | 04/12/2026 | $3,425.00 |
| 31/01/2027 | 13/02/2027 | $3,425.00 |
| 20/11/2027 | 03/12/2027 | $3,650.00 |
- Cycling through lush tea and spice plantations
- Periyar wildlife reserve, home to elephants, bison and tigers
- Climbing through cool air and pristine forests
- Drifting on a rice barge through Kerala’s backwaters
- Relaxing on white sands of Marari Beach
- Enjoying the best of Southern Indian Cuisine
Guided
Atlantic Escape
Guided Road Bike Tour
| Start Date | End Date | Price p.p. |
|---|---|---|
| 01/11/2025 Guaranteed | 10/11/2025 | $3,995.00 |
| 25/04/2026 | 04/05/2026 | $4,195.00 |
| 31/10/2026 | 09/11/2026 | $4,195.00 |
- Stunning Sintra and its sunsets
- The lovely fishing village of Nazare
- Incredible accommodation in 4 star hotels each night
- Views from the Arrabida mountains
- Coastal riding and beautiful beaches
- Reaching mainland Europe’s most southwesterly point by bike!
Guided
Badlands of Andalucia
Guided Gravel Riding Tour
| Start Date | End Date | Price p.p. |
|---|---|---|
| 02/11/2025 Guaranteed | 09/11/2025 | $3,135.00 |
- Spending the night in the magical city of Granada and riding out past the Alhambra as the adventure begins
- Riding through the vast forests of the Sierra Nevada
- Riding the Ramblas and through the incredible scenery of the Tabernas desert
- Arriving at the beautiful volcanic Cabo de Gata coastline
- Delicious seafood, sunset dinner on the coast
- The dramatic empty landscapes of the whole adventure
Guided
Road Atlas
Guided Road Bike Tour
| Start Date | End Date | Price p.p. |
|---|---|---|
| 08/11/2025 Fully Booked | 17/11/2025 | $2,525.00 |
| 27/12/2025 | 05/01/2026 | $2,525.00 |
| 31/01/2026 | 09/02/2026 | $2,710.00 |
| 07/11/2026 | 16/11/2026 | $2,710.00 |
| 27/12/2026 | 05/01/2027 | $2,710.00 |
| 30/01/2027 | 08/02/2027 | $2,850.00 |
| 06/11/2027 | 15/11/2027 | $2,850.00 |
| 27/12/2027 | 05/01/2028 | $2,850.00 |
- The High Atlas mountain range
- The outstanding Ounila Valley and Ait Benhaddou Kasbah
- Exploring the surreal blue rocks of Tafraoute
- The incredible 100km ride from Tafraoute towards the coast
- Enjoying a cold beer on one of Morocco’s finest terraces at Immouzer
- The sights, smells and sounds of the Marrakech souk
- Starting and finishing in this years ‘Capital of Culture’ Marrakech
Guided
Backroads and Beaches
Guided Bike Tour
| Start Date | End Date | Price p.p. |
|---|---|---|
| 08/11/2025 Last Spaces | 22/11/2025 | $3,850.00 |
| 10/01/2026 | 24/01/2026 | $4,135.00 |
| 14/02/2026 Fully Booked | 28/02/2026 | $4,135.00 |
| 07/11/2026 | 21/11/2026 | $4,135.00 |
| 13/02/2027 | 27/02/2027 | $4,135.00 |
| 06/11/2027 | 20/11/2027 | $4,135.00 |
- Eyeing up the elephants at Udawalawe
- Stunning Sigirya and the Lion Rock
- Colonial cool in Nuwara Eliya
- Coastal cycling and beautiful beaches
- Honing in on Horton Plains after a day in the hills
- The Knuckles and Kandy’s Temple of the Tooth
Guided
Roads of Ronda
Guided Road Bike Tour
| Start Date | End Date | Price p.p. |
|---|---|---|
| 09/11/2025 | 15/11/2025 | $2,995.00 |
- Staying in the quintessentially Spanish town of Old Ronda
- Cycling through the rugged, ‘bandit country’ of the Sierra de las Nieves
- Climbing the 1,200m up ‘The Colossus’
- The seemingly never-ending descent down to the fine sands of Estepona
- Taking a refreshing post ride dip in the Med
- Tasty tapas and sunset sangrias
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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