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            2027 Cycling Holidays To Book Now

            We found 6 Holidays in your search for:

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

            2026

            2027

            2028

            Level of Support

            We found 6 Holidays in your search for:

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

            2026

            2027

            2028

            Level of Support
            2027 Road Cycling Holidays 2027 Adventure Cycling Holidays 2027 Leisure Cycling Holidays 2027 Mountain Bike Holidays

            Planning ahead for your dream cycling holiday? Whether you're training to complete the UK's ultimate challenge ride - Land's End to John o' Groats - or searching for your trip of a lifetime in a far-flung destination, we know it’s helpful to plan ahead. These tours all have 2027 dates available to book now. Plus, you’ll only need to pay a deposit upfront to secure your space.

            What are you waiting for? Stop dreaming and start planning!

            • All Cycling Holidays
            • All Leisure Cycling Holidays
            • BOOK EARLY
            Select Order Order By
            Guided
            Guided
            United Kingdom

            Land's End to John O'Groats Explorer

            Guided Electric Bike Holiday

            Duration

            22 days

            Prices from

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

            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 DateEnd DatePrice p.p.
            20/06/2026
            Fully Booked
            11/07/2026£4,895.00
            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
            11/09/202702/10/2027£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
            Photo Highlights Dates
            Supported
            Supported
            United Kingdom

            C2C - Coast to Coast (Supported)

            Supported Leisure Cycling Holiday

            Duration

            5 days

            Prices from

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

            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 DateEnd DatePrice p.p.
            26/06/2026
            Last Spaces
            30/06/2026£895.00
            07/08/2026
            Fully Booked
            11/08/2026£895.00
            25/09/2026
            Guaranteed
            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
            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.
            17/07/2026
            Fully Booked
            22/07/2026£995.00
            18/09/2026
            Guaranteed
            23/09/2026£995.00
            25/06/202730/06/2027£1,025.00
            30/07/202704/08/2027£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
            Scotland

            Scotland - Lochs and Glens

            Guided Leisure Cycling Holiday

            Duration

            7 days

            Prices from

            £1,595 P.P.
            View Reviews
            8
            1
            2
            3
            4
            5
            Grade 3-4 : Moderate/Active
            More Info BOOK NOW

            Scotland - Lochs and Glens

            Guided Leisure Cycling Holiday

            LAST CHANCE OFFERS!

            Choose half-price bike hire or get 5% off tour departing 23 Aug 2026. Book before 01 June 2026 and enter promo code LETSGO26. Your discount will be applied once your booking is confirmed. Ts and Cs apply.

            Start DateEnd DatePrice p.p.
            14/06/2026
            Contact Us
            20/06/2026£1,595.00
            19/07/2026
            Guaranteed
            25/07/2026£1,595.00
            * 23/08/2026
            Guaranteed
            29/08/2026£1,595.00
            09/05/202715/05/2027£1,655.00
            13/06/202719/06/2027£1,655.00
            15/08/202721/08/2027£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
            Photo Highlights Dates
            Guided
            Guided
            Scotland

            Scotland - Hebridean Way

            Guided Leisure Cycling Holiday

            Duration

            7 days

            Prices from

            £2,555 P.P.
            View Reviews
            11
            1
            2
            3
            4
            5
            Grade 3-4 : Moderate/Active
            More Info BOOK NOW

            Scotland - Hebridean Way

            Guided Leisure Cycling Holiday

            LAST CHANCE OFFERS!

            Choose half-price bike hire or get 5% off tour departing 16 Aug 2026. Book before 01 June 2026 and enter promo code LETSGO26. Your discount will be applied once your booking is confirmed. Ts and Cs apply.

            Start DateEnd DatePrice p.p.
            24/05/2026
            Last Spaces
            30/05/2026£2,555.00
            31/05/2026
            Last Spaces
            06/06/2026£2,555.00
            21/06/2026
            Last Spaces
            27/06/2026£2,555.00
            05/07/2026
            Guaranteed
            11/07/2026£2,555.00
            26/07/2026
            Guaranteed
            01/08/2026£2,555.00
            * 16/08/2026
            Guaranteed
            22/08/2026£2,555.00
            30/08/2026
            Guaranteed
            05/09/2026£2,555.00
            02/05/202708/05/2027£2,635.00
            23/05/202729/05/2027£2,635.00
            06/06/202712/06/2027£2,635.00
            27/06/202703/07/2027£2,635.00
            08/08/202714/08/2027£2,635.00
            29/08/202704/09/2027£2,635.00
            12/09/202718/09/2027£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
            Photo Highlights Dates
            Guided
            Guided
            Scotland

            Scotland - The Caledonia Way

            Guided Leisure Cycling Holiday

            Duration

            8 days

            Prices from

            £2,095 P.P.
            View Reviews
            7
            1
            2
            3
            4
            5
            Grade 4: Active
            More Info BOOK NOW

            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 DateEnd DatePrice p.p.
            28/06/2026
            Last Spaces
            05/07/2026£2,095.00
            26/07/2026
            Contact Us
            02/08/2026£2,095.00
            06/09/2026
            Last Spaces
            13/09/2026£2,095.00
            02/05/202709/05/2027£2,185.00
            23/05/202730/05/2027£2,185.00
            11/07/202718/07/2027£2,185.00
            05/09/202712/09/2027£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
            Photo Highlights Dates

            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
            Quote
            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
            Quote
            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
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