Some trips are best reserved early before they fill up. Now that our 2027 dates are live, we've pulled together a handy list so you don't miss out. Take your pick from popular road cycling challenges to e-bike rides through the Tuscan countryside and off-road adventures in Spain and Italy. And if nothing in the most popular list takes your fancy, you'll find 2027 dates up across our cycling ranges, so go on, have a browse and book with a deposit today!
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Destinations (82)
Types of Cycling / Grades (1)
Departure Month
Level of Support
Destinations (82)
Types of Cycling / Grades (1)
Departure Month
Level of Support
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Guided
Scotland - The Caledonia Way
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. |
|---|---|---|
| 26/07/2026 Contact Us | 02/08/2026 | £2,095.00 |
| 06/09/2026 Last Spaces | 13/09/2026 | £2,095.00 |
| 02/05/2027 | 09/05/2027 | £2,185.00 |
| 23/05/2027 | 30/05/2027 | £2,185.00 |
| 11/07/2027 | 18/07/2027 | £2,185.00 |
| 05/09/2027 | 12/09/2027 | £2,185.00 |
- Marvelling at the beauty of Kilmartin Glen and its ancient monuments
- Enjoying traffic-free Caledonia Way cycleways and lovely canal side routes
- Checking out Ben Nevis and The Grampians from Loch Linhe
- Fort Augustus and taking on the legendary ascent of Glendoe
- Exploring Knapdale – One of Scotland’s National Scenic Areas
- Cycling to Scotland’s best-loved towns including Fort William and Fort Augustus
Guided
NEW! Andalucia - Costa de la Luz and Ancient Cadiz
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. |
|---|---|---|
| 17/10/2026 Last Spaces | 24/10/2026 | £2,295.00 |
| 20/10/2026 Guaranteed | 27/10/2026 | £2,295.00 |
| 30/03/2027 | 06/04/2027 | £2,325.00 |
| 06/06/2027 | 13/06/2027 | £2,325.00 |
| 19/09/2027 | 26/09/2027 | £2,325.00 |
- Exploring the endless coastal trails surrounding Tarifa
- Indulging in delicious, freshly-caught seafood in Sanlucar
- Savouring a glass of sherry in a historic bodega within the Sherry Triangle
- Immersing ourselves in true Andalucian culture and enjoying some Flamenco
- Riding along the peaceful, traffic-free EuroVelo routes
- Experiencing the lively, vibrant town of Tarifa, the gateway to two continents
Supported
C2C - Coast to Coast (Supported)
Supported 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. 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. |
|---|---|---|
| 07/08/2026 Last Spaces | 11/08/2026 | £895.00 |
| 25/09/2026 Fully Booked | 29/09/2026 | £895.00 |
| 21/05/2027 | 25/05/2027 | £925.00 |
| 16/07/2027 | 20/07/2027 | £925.00 |
| 06/08/2027 | 10/08/2027 | £925.00 |
| 27/08/2027 | 31/08/2027 | £925.00 |
| 24/09/2027 | 28/09/2027 | £925.00 |
- UK’s favourite long distance cycle route
- Dramatic landscapes of the Lake District and Pennines
- Cycle friendly route – cycle paths and quiet country lanes
- Fully supported and awesome Skedaddle lunches
- Bike friendly B&Bs offering mouthwatering breakfasts
- Great sense of achievement, crossing the country, coast to coast
Guided
Guided
Italy
NEW! Emilia-Romagna - The Food Valley
Guided Leisure Cycling Holiday
Duration
8 daysPrices from
£1,995 P.P.
Grade 2-3: Gentle/Moderate
NEW! Emilia-Romagna - The Food Valley
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. |
|---|---|---|
| 29/08/2026 Fully Booked | 05/09/2026 | £1,995.00 |
| 24/04/2027 | 01/05/2027 | £2,085.00 |
| 29/05/2027 | 05/06/2027 | £2,085.00 |
| 18/09/2027 | 25/09/2027 | £2,085.00 |
- Riding along 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 Busseto and Roncole, where the famous Italian composer Giuseppe Verdi was born
- Exploring modern and bustling Modena
- Taking in the vibrant university city of Bologna
Guided
Scotland - Hebridean Way
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. |
|---|---|---|
| 05/07/2026 Fully Booked | 11/07/2026 | £2,555.00 |
| 26/07/2026 Fully Booked | 01/08/2026 | £2,555.00 |
| * 16/08/2026 Last Spaces | 22/08/2026 | £2,555.00 |
| 30/08/2026 Fully Booked | 05/09/2026 | £2,555.00 |
| 02/05/2027 | 08/05/2027 | £2,635.00 |
| 23/05/2027 | 29/05/2027 | £2,635.00 |
| 06/06/2027 | 12/06/2027 | £2,635.00 |
| 27/06/2027 | 03/07/2027 | £2,635.00 |
| 08/08/2027 | 14/08/2027 | £2,635.00 |
| 29/08/2027 | 04/09/2027 | £2,635.00 |
| 12/09/2027 | 18/09/2027 | £2,635.00 |
- Riding along the Golden Road
- Miles and miles of picture-perfect white sand beaches
- Enjoying a wee dram from the Distillery at Tarbert
- Seeing the traditional weaving of Harris Tweed
- Views of Luskentyre Beach over a delicious picnic lunch
- Visiting the Blackhouse Village at Gearrannan
- The awe inspiring Callanish Standing Stones
Guided
Tuscany to Rome
Guided Electric Bike Holiday
E-BIKE HOLIDAY
This holiday has been designed as an e-bike tour allowing 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.
| Start Date | End Date | Price p.p. |
|---|---|---|
| 12/09/2026 Last Spaces | 19/09/2026 | £2,395.00 |
| 08/05/2027 | 15/05/2027 | £2,495.00 |
| 04/09/2027 | 11/09/2027 | £2,495.00 |
- Staying in Tuscan accommodation overlooking stunning landscapes
- Discovering the amazing towns of Siena, San Quirico and Pienza
- Sampling the best wines of Chianti, Montepulciano and Montalcino
- Enjoying the journey from Tuscany to Rome on a variety of terrain, including ancient Roman roads
- Exploring the lesser-known historical towns of Lazio, such as Sutri with it’s Roman amphitheatre
- The sense of achievement riding into St Peter’s Square in Rome
Guided
Land's End to John O'Groats Explorer
Guided Electric Bike Holiday
E-BIKE HOLIDAY
This holiday has been designed as an e-bike tour allowing 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.
| Start Date | End Date | Price p.p. |
|---|---|---|
| 01/08/2026 Guaranteed | 22/08/2026 | £4,895.00 |
| 17/04/2027 Guaranteed | 08/05/2027 | £5,045.00 |
| 19/06/2027 Guaranteed | 10/07/2027 | £5,045.00 |
| 11/09/2027 | 02/10/2027 | £5,045.00 |
- 3 countries in 19 days of riding
- 1,000 miles of Britain at its best
– Riding an e-bike the length of Britain from toe to tip and declaring yourself an ‘End to Ender’
- Cornish pasties to haggis and everything in between
- Experiencing the regional changes in tradition, culture and accents as you progress from county to county
- Enjoying spectacular scenery from Cheddar Gorge to the Cairngorms
Guided
Scotland - Lochs and Glens
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. |
|---|---|---|
| 19/07/2026 Fully Booked | 25/07/2026 | £1,595.00 |
| 23/08/2026 Guaranteed | 29/08/2026 | £1,595.00 |
| 09/05/2027 | 15/05/2027 | £1,655.00 |
| 13/06/2027 | 19/06/2027 | £1,655.00 |
| 15/08/2027 | 21/08/2027 | £1,655.00 |
- Watching the sun rise over Loch Lomond
- The beautiful lochs of Venachar, Lubnaig and Tay
- Cycling through the dramatic Cairngorms National Park
- Scottish wildlife at its best including deer, red squirrels, eagles and osprey
- Castles and distilleries galore
- Rural Scottish cycling at its very best
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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