What are ‘Guaranteed Departures’? Our group trips need a minimum number of riders before we can give things the go ahead. Our Guaranteed Departures are trips which have already reached that minimum, meaning you can place a booking and start looking forward to your trip straight away. Browse all upcoming Guaranteed Departures below and click on the ‘Dates’ tab to see all available tour dates for a particular holiday. If the group tour you are looking at is not yet guaranteed, then you can still make a booking and chat to our sales team about how many more riders are needed before it becomes guaranteed.
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Guided
Wessex - King Alfred's Way
Guided Mountain Bike Holiday
Guided
United Kingdom
Wessex - King Alfred's Way
Guided Mountain Bike Holiday
Start
26/07/2026Duration
8 daysPrices from
£1,995 P.P.
Grade 3 : Moderate
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 | Price p.p. |
|---|---|
| 26/07/2026 | £1,995.00 |
| 13/09/2026 | £1,995.00 |
Highlighted trips are already guaranteed
- Visiting historic Winchester and its Cathedral (and the King Alfred the Great Statue)
- Enjoying chalky hillsides and rolling countryside
- Riding short, technical ascents and soaring downhill on the South Downs and The Ridgeway
- Escaping from busy southern urban cities on ancient paths and rough tracks
- Biking a mix of undulating terrain on Salisbury Plain and South Downs Way
- Experiencing 10,000 years of history
- Marvelling at Stonehenge
Guided
Land's End to John O'Groats Explorer
Guided Electric Bike Holiday
Guided
United Kingdom
Land's End to John O'Groats Explorer
Guided Electric Bike Holiday
Start
01/08/2026Duration
22 daysPrices from
£4,895 P.P.
Grade 3-4 : Moderate/Active
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 | Price p.p. |
|---|---|
| 01/08/2026 | £4,895.00 |
| 17/04/2027 | £5,045.00 |
| 19/06/2027 | £5,045.00 |
| 11/09/2027 | £5,045.00 |
Highlighted trips are already guaranteed
- 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
Northumberland - Reivers Trails
Guided Gravel Riding Holiday
Guided
United Kingdom
Northumberland - Reivers Trails
Guided Gravel Riding Holiday
Start
02/08/2026Duration
7 daysPrices from
£1,595 P.P.
Grade 3 : Moderate
| Start Date | Price p.p. |
|---|---|
| 02/08/2026 | £1,595.00 |
| 20/06/2027 | £1,655.00 |
| 15/08/2027 | £1,655.00 |
Highlighted trips are already guaranteed
- Miles and miles of traffic-free gravel Reivers trails to explore
- A raid across the Scottish Border and a night in Newcastleton, Liddesdale
- A chance to spot ospreys which have nested in Kielder since 2008
- A visit to the Skyspace installation designed by artist James Turrell
- Fabulous vistas across Europe’s largest man-made lake
- The flowing contours and switchbacks of Kielder’s Lakeside Trail
- A delicious local pint from First and Last’s Bellingham-based brewery
Supported
C2C - Coast to Coast (Supported)
Supported Leisure Cycling Holiday
Supported
United Kingdom
C2C - Coast to Coast (Supported)
Supported Leisure Cycling Holiday
Start
07/08/2026Duration
5 daysPrices from
£895 P.P.
Grade 3-4 : Moderate/Active
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 | Price p.p. |
|---|---|
| 26/06/2026 | £895.00 |
| 07/08/2026 | £895.00 |
| 25/09/2026 | £895.00 |
| 21/05/2027 | £925.00 |
| 16/07/2027 | £925.00 |
| 06/08/2027 | £925.00 |
| 27/08/2027 | £925.00 |
| 24/09/2027 | £925.00 |
Highlighted trips are already guaranteed
- 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
Scotland - Tour d'Ecosse
Guided Road Cycling Holiday
Guided
Scotland
Scotland - Tour d'Ecosse
Guided Road Cycling Holiday
Start
08/08/2026Duration
8 daysPrices from
£1,855 P.P.
Grade 3 : Moderate
| Start Date | Price p.p. |
|---|---|
| 04/07/2026 | £1,855.00 |
| 08/08/2026 | £1,855.00 |
| 05/09/2026 | £1,855.00 |
| 08/05/2027 | £1,925.00 |
| 26/06/2027 | £1,925.00 |
| 07/08/2027 | £1,925.00 |
| 04/09/2027 | £1,925.00 |
Highlighted trips are already guaranteed
- Quiet single-track roads for miles on end
- Bealach Na Ba – the greatest road ascent in the UK
- Feasting on fresh seafood after a day in the saddle
- Stunning views out over the Isle of Skye
- Cycling the peaceful lochside roads of Scotland
- The swooping coastal road from Ullapool to Kinlochewe
Guided
NEW! Wales - Traws Eryri
Guided Mountain Bike Holiday
Guided
Wales
NEW! Wales - Traws Eryri
Guided Mountain Bike Holiday
Start
09/08/2026Duration
7 daysPrices from
£1,795 P.P.
Grade 3 - 4: Moderate/ Challenging
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 | Price p.p. |
|---|---|
| 09/08/2026 | £1,795.00 |
| 16/05/2027 | £1,865.00 |
| 18/07/2027 | £1,865.00 |
Highlighted trips are already guaranteed
- Exploring rugged mountains, isolated forests, and vast open landscapes with panoramic views in Eryri National Park.
- Riding some of the best MTB trails in Wales on the Coed y Brenin, Penmachno and Mach Trails.
- Tackling steep climbs and exhilarating rocky descents on the ancient Sarn Helen Roman Road.
- Experiencing Welsh history and heritage, as we pass abandoned slate quarries, traditional villages and finish at Conwy’s medieval castle.
- Indulging in a local pint and home-cooked pub food to end rewarding days in the saddle.
Guided
Scotland - Hebridean Way
Guided Leisure Cycling Holiday
Guided
Scotland
Scotland - Hebridean Way
Guided Leisure Cycling Holiday
Start
16/08/2026Duration
7 daysPrices from
£2,555 P.P.
Grade 3-4 : Moderate/Active
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 | Price p.p. |
|---|---|
| 05/07/2026 | £2,555.00 |
| 26/07/2026 | £2,555.00 |
| * 16/08/2026 | £2,555.00 |
| 30/08/2026 | £2,555.00 |
| 02/05/2027 | £2,635.00 |
| 23/05/2027 | £2,635.00 |
| 06/06/2027 | £2,635.00 |
| 27/06/2027 | £2,635.00 |
| 08/08/2027 | £2,635.00 |
| 29/08/2027 | £2,635.00 |
| 12/09/2027 | £2,635.00 |
Highlighted trips are already guaranteed
- 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
Cycling Safari
Guided Cycling Holiday
Guided
Eswatini (Swaziland)
Cycling Safari
Guided Cycling Holiday
Start
20/08/2026Duration
11 daysPrices from
£3,415 P.P.
Grade 3 : Moderate
| Start Date | Price p.p. |
|---|---|
| 20/08/2026 | £3,415.00 |
| 08/10/2026 | £3,415.00 |
| 01/04/2027 | £3,655.00 |
| 19/08/2027 | £3,655.00 |
| 07/10/2027 | £3,655.00 |
Highlighted trips are already guaranteed
- Explore the diverse regions of this amazing country
- Experience some fantastic ‘off the beaten path’ cycling
- Stay in amazing accommodation, full of character
- Discover an incredible range of wildlife
- Sample a wide range of great local food
- Get to know the super-friendly local people
Guided
Land's End to John O'Groats Classic
Guided Road Cycling Holiday
Guided
United Kingdom
Land's End to John O'Groats Classic
Guided Road Cycling Holiday
Start
22/08/2026Duration
16 daysPrices from
£3,295 P.P.
Grade 3 - 4: Moderate/ Challenging
| Start Date | Price p.p. |
|---|---|
| * 22/08/2026 | £3,295.00 |
| 22/05/2027 | £3,395.00 |
| 14/08/2027 | £3,395.00 |
Highlighted trips are already guaranteed
- Ride the length of Britain from toe to tip and declare yourself an ‘End to Ender’
- The camaraderie of completing the UK’s best challenge ride on a small group tour
- 3 countries in 14 days of riding. 1,000 miles of Britain at its best
- A unique LEJOG route along quiet roads through scenic countryside
- Enjoy spectacular scenery from Cheddar Gorge to the Cairngorms
- Experience the regional changes in tradition, culture and accents as you progress from county to county
- Delicious picnics, country pubs and wonderful accommodation
- Cornish pasties to haggis and everything in between
Guided
Alps and Dolomites - Giants of the Giro
Guided Road Cycling Holiday
Guided
Italy
Alps and Dolomites - Giants of the Giro
Guided Road Cycling Holiday
Start
22/08/2026Duration
9 daysPrices from
£2,495 P.P.
Grade 4 - 5: Challenging/ Demanding
| Start Date | Price p.p. |
|---|---|
| 25/07/2026 | £2,495.00 |
| 22/08/2026 | £2,495.00 |
| 17/07/2027 | £2,595.00 |
| 21/08/2027 | £2,595.00 |
Highlighted trips are already guaranteed
- Cycling through the best alpine and dolomite scenery of Italy
- Climbing the iconic Mortirolo, Passo Gavia and Passo Stelvio of Giro d’Italia fame
- Enjoying post-ride relaxation in typical chalet-style mountain hotels
- Re-charging your energy levels every evening with tasty local fayre
- Testing your legs and endurance on the final Monte Grappa climb
- Enjoying an aperitif in the lively towns of San Pellegrino Terme, Bormio and Bassano del Grappa
Guided
La Via Claudia
Guided Leisure Cycling Holiday
Guided
Austria & Italy
La Via Claudia
Guided Leisure Cycling Holiday
Start
22/08/2026Duration
8 daysPrices from
£2,495 P.P.
Grade 3-4 : Moderate/Active
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 | Price p.p. |
|---|---|
| 18/07/2026 | £2,495.00 |
| 22/08/2026 | £2,495.00 |
| 19/06/2027 | £2,595.00 |
| 03/07/2027 | £2,595.00 |
| 21/08/2027 | £2,595.00 |
Highlighted trips are already guaranteed
- Waking up to beautiful views of the Zugspitze, Germany’s highest peak
- Cycling beside the vivid blue waters of the River Inn
- Absorbing the history of an ancient trade route by bike
- Exploring Merano – The Jewel of South Tyrol
- Winding your way through the lovely Vinschgau Valley
- A post-ride, tasty gelato on the shores of Lake Garda
Guided
Scotland - Lochs and Glens
Guided Leisure Cycling Holiday
Guided
Scotland
Scotland - Lochs and Glens
Guided Leisure Cycling Holiday
Start
23/08/2026Duration
7 daysPrices from
£1,595 P.P.
Grade 3-4 : Moderate/Active
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 | Price p.p. |
|---|---|
| 19/07/2026 | £1,595.00 |
| 23/08/2026 | £1,595.00 |
| 09/05/2027 | £1,655.00 |
| 13/06/2027 | £1,655.00 |
| 15/08/2027 | £1,655.00 |
Highlighted trips are already guaranteed
- 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
