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            Small Group Leisure Cycling Holidays

            We found 21 Holidays in your search for:

            Destinations (82)
            Types of Cycling / Grades (1)
            Departure Month

            2026

            2027

            2028

            Level of Support

            We found 21 Holidays in your search for:

            Select Order Order By
            Destinations (82)
            Types of Cycling / Grades (1)
            Departure Month

            2026

            2027

            2028

            Level of Support

            Join a group of likeminded riders on a small group holiday with Skedaddle! Whether you’re looking to join as a couple, group of friends, or as a solo traveller, you’ll feel part of one passionate pedallin’ community. Our tour leaders and guides will be on hand throughout your trip to ensure everything runs smoothly. You’ll also have a dedicated support vehicle to assist with everything from mechanical issues to emergency back-up and extra supplies.

            On a group tour, we take care of all your accommodation and luggage transfers. The only thing you’ll need to focus on is turning the pedals, enjoying the beautiful scenery and wondering what you’ll have for lunch (did we mention the legendary Skedaddle picnics?). It’s no wonder our small group tours are so popular!

            • All Cycling Holidays
            • All Leisure Cycling Holidays
            • SMALL GROUP CYCLING HOLIDAYS

            Page 1 of 3

            Select Order Order By
            Supported
            Supported
            United Kingdom

            C2C - Coast to Coast

            Supported Leisure Cycling Holiday

            Duration

            5 days

            Prices from

            £895 P.P.
            View Reviews
            4
            1
            2
            3
            4
            5
            Grade 3-4 : Moderate/Active
            More Info BOOK NOW

            C2C - Coast to Coast

            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 DateEnd DatePrice p.p.
            25/09/2026
            Fully Booked
            29/09/2026£895.00
            21/05/202725/05/2027£925.00
            16/07/202720/07/2027£925.00
            06/08/202710/08/2027£925.00
            27/08/202731/08/2027£925.00
            24/09/202728/09/2027£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
            Photo Highlights Dates
            Guided
            Guided
            United Kingdom

            Norfolk - Rebellion Way

            Guided Leisure Cycling Holiday

            Duration

            7 days

            Prices from

            £1,695 P.P.
            View Reviews
            9
            1
            2
            3
            4
            5
            Grade 3 : Moderate
            More Info BOOK NOW

            Norfolk - Rebellion 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.

            • Coastal cycling, beach houses and British seaside sights
            • Majestic manor houses and villages full of character and charm
            • Varied terrain from rolling country lanes to wooded ways
            • Tales of Boudicca and rebellions
            • Delightful Diss and stunning Holkham Hall
            • Miles of gentle pedalling through the Norfolk Broads
            • Posing with Captain Mainwaring in Thetford
            Photo Highlights Dates
            Supported
            Supported
            United Kingdom

            Hadrian's Cycleway

            Supported Leisure cycling holiday

            Duration

            6 days

            Prices from

            £995 P.P.
            View Reviews
            15
            1
            2
            3
            4
            5
            Grade 3 : Moderate
            More Info BOOK NOW

            Hadrian's Cycleway

            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.

            Start DateEnd DatePrice p.p.
            18/09/2026
            Fully Booked
            23/09/2026£995.00
            25/06/202730/06/2027£1,025.00
            03/09/202708/09/2027£1,025.00
            • The well-preserved Hadrian’s Wall forts of Birdoswald and Vindolanda
            • The rugged beauty of the North Pennines
            • The picturesque market town of Corbridge
            • The view down the Tyne as you arrive into Newcastle
            • The sense of achievement having ridden from coast to coast
            • Following in the footsteps of the Roman Empire
            Photo Highlights Dates
            Guided
            Guided
            Austria & Italy

            La Via Claudia

            Guided Leisure Cycling Holiday

            Duration

            8 days

            Prices from

            £2,595 P.P.
            View Reviews
            26
            1
            2
            3
            4
            5
            Grade 3-4 : Moderate/Active
            More Info BOOK NOW

            La Via Claudia

            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 DateEnd DatePrice p.p.
            19/06/2027
            Guaranteed
            26/06/2027£2,595.00
            03/07/202710/07/2027£2,595.00
            21/08/202728/08/2027£2,595.00
            • 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
            Photo Highlights Dates
            Guided
            Guided
            Italy

            Sardinia - Island Flavours

            Guided Leisure Cycling Holiday

            Duration

            8 days

            Prices from

            £1,995 P.P.
            View Reviews
            5
            1
            2
            3
            4
            5
            Grade 3 : Moderate
            More Info BOOK NOW

            Sardinia - Island Flavours

            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 DateEnd DatePrice p.p.
            10/10/2026
            Fully Booked
            17/10/2026£1,995.00
            17/04/202724/04/2027£2,095.00
            01/05/202708/05/2027£2,095.00
            11/09/202718/09/2027£2,095.00
            09/10/202716/10/2027£2,095.00
            • Checking out the UNESCO heritage site of Barumini Nuraghe
            • Enjoying the long descent to Fluminimaggiore and Masua
            • Sampling local specialties at Carloforte, on St Pietro island
            • Riding along the Nebida coastline and marvelling at the view of Pan di Zucchero
            • Experiencing the friendliness and hospitality of the Sardinian people
            • Discovering the white beaches along the south-west coastal road
            Photo Highlights Dates
            Supported
            Supported
            United Kingdom

            Way of the Roses

            Supported Leisure Cycling Holiday

            Duration

            6 days

            Prices from

            £1,095 P.P.
            View Reviews
            4
            1
            2
            3
            4
            5
            Grade 3 : Moderate
            More Info BOOK NOW

            Way of the Roses

            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.

            Start DateEnd DatePrice p.p.
            20/09/2026
            Contact Us
            25/09/2026£1,095.00
            25/04/202730/04/2027£1,125.00
            20/06/202725/06/2027£1,125.00
            26/09/202701/10/2027£1,125.00
            • Posing at Eric Morecambe’s statue on Morecambe seafront
            • Cycling through the Forest of Bowland & Yorkshire Dales
            • Superb local ales and tasty food every night
            • York – flat cycling, big Minster
            • The chalky rolling hills, with big country views of the Wolds
            • Fish & chips on Bridlington’s waterfront to celebrate your ride!
            Photo Highlights Dates
            Guided
            Guided
            United Kingdom

            Northumberland - Alnmouth

            Guided Leisure Cycling Holiday

            Duration

            5 days

            Prices from

            £1,195 P.P.
            1
            2
            3
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            5
            Grade 2: Gentle
            More Info BOOK NOW

            Northumberland - Alnmouth

            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.

            • Stay at Nether Grange, Alnmouth – a comfortable HF Country House a stone’s throw from the beach
            • Ride along the beautiful Northumberland coast to Craster harbour
            • Explore the peaceful country roads of Northumberland and the market town of Alnwick
            • Visit the priory on Holy Island (depending on tides) and take in the majesty of Warkworth Castle
            • Admire the mighty fortifications of Alnwick, Bamburgh and Dunstanburgh castles
            • Explore part of the Coast and Castles route that runs from Newcastle to Edinburgh
            Photo Highlights Dates
            Guided
            Guided
            Italy

            Puglia

            Guided Leisure Cycling Holiday

            Duration

            8 days

            Prices from

            £2,295 P.P.
            View Reviews
            12
            1
            2
            3
            4
            5
            Grade 2: Gentle
            More Info BOOK NOW

            Puglia

            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 DateEnd DatePrice p.p.
            20/09/2026
            Fully Booked
            27/09/2026£2,295.00
            10/04/202717/04/2027£2,395.00
            18/09/202725/09/2027£2,395.00
            • 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
            Photo Highlights Dates
            Guided
            Guided
            United Kingdom

            Cotswolds - Bourton-on-the-Water

            Guided Leisure Cycling Holiday

            Duration

            5 days

            Prices from

            £1,025 P.P.
            View Reviews
            2
            1
            2
            3
            4
            5
            Grade 2-3: Gentle/Moderate
            More Info BOOK NOW

            Cotswolds - Bourton-on-the-Water

            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.

            • Staying at Harrington House, a comfortable HF Country House in the centre of picturesque Bourton-on-the-Water
            • Three days guided cycling with an experienced leader
            • Enjoying leisurely rides through beautiful rolling countryside
            • Visiting the famous Cotswold market town of Stow-on-the-Wold
            • Visiting the historic village of Bibury, famous for its stone cottages which once housed weavers
            • Cycling through beautiful chocolate box villages
            Photo Highlights Dates
            Guided
            Guided
            United Kingdom

            Lake District - Derwent Water

            Guided Leisure Cycling Holiday

            Duration

            5 days

            Prices from

            £1,045 P.P.
            View Reviews
            8
            1
            2
            3
            4
            5
            Grade 2-3: Gentle/Moderate
            More Info BOOK NOW

            Lake District - Derwent Water

            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.

            • Stay at Derwent Bank, Keswick – a comfortable HF Country House sitting directly on the banks of Derwent Water
            • Spin your legs gently along country lanes or challenge them as you climb up towards some Lakeland fells
            • Admire the vista across the lake to Skiddaw and Blencathra
            • Treat yourself to delicious cake pit-stops in charming local cafés
            • Let the lovely Lakeland landscapes inspire your daily cycling
            • Visit Castlerigg Stone Circle – an ancient monument built around 3000 BC
            Photo Highlights Dates
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            Not sure which trip's right for you? Just ask!

            Get in touch and we'll help you find your perfect trip.

            Quote
            What one pays for is not having to worry about anything – and Skedaddle does an excellent job taking care of us. We haven’t tried the other tour companies but why bother when Skedaddle is top notch.
            Roger, France - Chateaux of the Loire
            Quote
            The guides and other group members really made the holiday enjoyable. Our guide was friendly, professional and knowledgeable.
            Elaine, Italy - Tuscany to Rome
            Quote
            All the services we received were first class. This was a real holiday and going with Skedaddle took all the stress of booking accommodation from home, route planning and so on, so all we had to do was enjoy the cycling. This has been one of the best holidays in my life.
            Alison, Italy - Sardinia Island Flavours
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            What do you like most about Skedaddle? Where do I start? The booking process, the hotels, the guides, the lunches, the places they go, the people I meet, the pit stops, the Skedaddle community, reliability, I can put my trust in them to provide a great and memorable experience.
            David, Austria & Italy - La Via Claudia
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            Skedaddle holidays are always great; you can ride your bike and they pretty much do the rest! Being able to use two wheels as a mode of transport to travel across the country, supported by Skedaddle, just shows the beauty, and power, of bikes. Thank you for making it possible!
            Kate, UK - C2C
            Quote
            We just LOVED the whole thing – route, weather, food, scenery, being outside – it was probably one of the best holidays we have had.
            Inese, Austria - The Danube Cyclepath
            Next

            News, Reviews & Stories

            Cycling on the Hadrian's Cycleway long distance cycle route

            7 Must-Do long distance cycle routes on the National Cycle Network

            If you’re looking for long distance cycle routes in the UK, you’ll likely have encountered the little blue and red signs marking the incredible National Cycle Network. For more than 30 years, Walk Wheel Cycle Trust has been the custodian of this network, developing and maintaining routes that make exploring the UK by bike more ...

            Amy McKie
            Amy McKie
            September 11, 2026
            Riding along the southern spain coastline on the badlands of spain

            9 must-ride Spanish cycling routes  

            Spanish cycling routes offer some of Europe's most rewarding riding, from dramatic mountain passes and quiet coastal roads to rolling vineyards and remote pueblos blancos (white villages). Few people know these bike tours in Spain better than Dan Hirst, Head of Skedaddle España. Dan has spent more than two decades living near Tarifa, mainland Spain's ...

            Dan Hirst, Head of Skedaddle Espana
            Dan Hirst
            September 4, 2026
            Cycling in the Pyrenees

            Cycling in the Pyrenees: A Tale of Two Journeys – France versus Spain

            The majestic Pyrenees mountain range, forming a natural border between France and Spain, has long attracted cyclists seeking both challenge and charm. Cycling in the Pyrenees offers exhilarating road cycling adventures, with stunning landscapes, diverse climates, and rich culture to discover. Skedaddle offers two distinct road cycling holidays through this rugged terrain. The Trans Pyrenees ...

            Hannah Reynolds
            September 4, 2026

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