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            2027 Cycling Holidays You Can Book Now

            We found 63 Holidays in your search for:

            Destinations (82)
            Types of Cycling / Grades (7)
            Departure Month

            2026

            2027

            2028

            Level of Support

            We found 63 Holidays in your search for:

            Select Order Order By
            Destinations (82)
            Types of Cycling / Grades (7)
            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
            • BOOK EARLY

            Page 5 of 7

            Select Order Order By
            Self-Guided
            Self-Guided
            United Kingdom

            Hadrian's Cycleway (6 days cycling)

            Self-Guided Family Cycling Holiday

            Duration

            7 days

            Prices from

            £895 P.P.
            1
            2
            3
            4
            5
            Grade 1 - 2 : Easy/Gentle
            More Info BOOK NOW

            Hadrian's Cycleway (6 days cycling)

            Self-Guided Family Cycling Holiday

            Child Discounts

            Daily departures available from April to mid October.

            Choose your own dates from:

            2026 £895 per person

            2027 £915 per person

            You either can make a booking online or over the phone. Once we have your details, we’ll be able to check availability.

            Kid’s Discounts

            For children below the age of 18 who are travelling with 2 full-paying passengers, we are able to offer a 20% discount off the basic holiday cost.

            If you‘re happy sharing a family room, once we’ve received your booking we will check what rooms are available and we may be able to offer (up to) an additional 20% discount for the children (subject to availability).

            • Cycling next to Hadrian’s Wall near Birdoswald
            • Beating your parents up one of the cheeky Skedaddle climbs
            • Seeing a live archaeological dig at Vindolanda
            • Corbridge and sinking a well-deserved pint of local ale – it’s not all about the kids you know!!
            • Seeing who’ll be the first to spot the ‘Blinking Eye’ bridge in Newcastle
            • Ice cream in Tynemouth and the sense of achievement having ridden from coast to coast as a family
            Photo Highlights Dates
            Self-Guided
            Self-Guided
            United Kingdom

            C2C - Coast to Coast (5 Days Cycling)

            Self-Guided Family Cycling Holiday

            Duration

            6 days

            Prices from

            £1,065 P.P.
            1
            2
            3
            4
            5
            Grade 3 : Moderate
            More Info BOOK NOW

            C2C - Coast to Coast (5 Days Cycling)

            Self-Guided Family Cycling Holiday

            Child Discounts

            Daily departures available from April to end of September. If you‘re interested in doing this holiday in October please call and chat to us.

            Choose your own dates from:

            2026 and 2027 £1065 per person

            Due to some big events happening in Newcastle in July and September 2026, it’s not possible to start this tour in Newcastle between the 08th and 10th Jul, or the 10th and 14th Sep, but do chat to us if you have set dates, as we can likely organise a Penrith start for you.

            You can either make a booking online or over the phone. Once we have your details, we’ll be able to check availability.

            Kid’s Discounts

            For children below the age of 18 who are travelling with 2 full-paying passengers, we are able to offer a 20% discount off the basic holiday cost.

            If you‘re happy sharing a family room, once we’ve received your booking we will check what rooms are available and we may be able to offer (up to) an additional 20% discount for the children (subject to availability).

            • UK’s favourite long distance cycle route
            • Dramatic English landscapes
            • Cycle friendly route
            • Stress-free cycling complimented with an abundance of pubs and cafes en route
            • Bike friendly B&Bs offering mouth-watering breakfasts
            • Suitable for adults and older children
            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
            6
            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
            Guided
            Guided
            South Korea

            Seoul to Busan

            Guided Cycling Holiday

            Duration

            13 days

            Prices from

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

            Seoul to Busan

            Guided Cycling Holiday

            Start DateEnd DatePrice p.p.
            17/10/2026
            Fully Booked
            29/10/2026£4,995.00
            31/10/202612/11/2026£4,995.00
            17/04/202729/04/2027£4,995.00
            16/10/202728/10/2027£4,995.00
            • Seoul – Cool art, sights and shopping
            • Bustling Busan, Jagalchi fish market and Gamcheon
            • Historic Gyeongju and Andong’s Hahoe Cultural Village
            • K-Pop, culture and delicious cuisine
            • Traffic-free cycle paths and rural riding
            • Hot springs and misty mountains
            Photo Highlights Dates
            Guided
            Guided
            United Kingdom

            Northumberland - Reivers Trails

            Guided Gravel Riding Holiday

            Duration

            7 days

            Prices from

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

            Northumberland - Reivers Trails

            Guided Gravel Riding Holiday

            LAST CHANCE OFFERS!

            Choose half-price bike hire or get 5% off tour departing 21 Jun 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.
            * 21/06/2026
            Guaranteed
            27/06/2026£1,595.00
            02/08/2026
            Guaranteed
            08/08/2026£1,595.00
            20/06/202726/06/2027£1,655.00
            15/08/202721/08/2027£1,655.00
            • 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
            Photo Highlights Dates
            Guided
            Guided
            Scotland

            Scotland - Wild About Argyll

            Guided Gravel Riding Holiday

            Duration

            7 days

            Prices from

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

            Scotland - Wild About Argyll

            Guided Gravel Riding Holiday

            Start DateEnd DatePrice p.p.
            07/06/2026
            Fully Booked
            13/06/2026£1,695.00
            12/07/202618/07/2026£1,695.00
            09/08/202615/08/2026£1,695.00
            30/08/202605/09/2026£1,695.00
            06/06/202712/06/2027£1,755.00
            01/08/202707/08/2027£1,755.00
            12/09/202718/09/2027£1,755.00
            • Scenic shorelines on Loch Goil, Loch Long and Loch Eck
            • Lush forest with a variety of trails and textbook gravel riding
            • Pairing Scotland’s finest seafood with local whisky and craft beer
            • Deep glens beneath towering mountains in Loch Lomond & the Trossachs National Park
            • Sunsets across Loch Fyne at Portavadie
            • Chance to spot otters, red squirrels and white-tailed eagles
            Photo Highlights Dates
            Self-Guided
            Self-Guided
            United Kingdom

            Cotswolds to Windsor

            Self-Guided Leisure Cycling Holiday

            Duration

            5 days

            Prices from

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

            Cotswolds to Windsor

            Self-Guided Leisure Cycling Holiday

            E-BIKE HIRE AVAILABLE

            This holiday is well-suited to both regular bikes and pedal assist e-bikes, and you can choose to hire either when you book your holiday 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.

            Daily departures available from April to mid October.

            Choose your own dates from:

            2026 £1095 per person

            2027 £1120 per person

            For a group of 4 or more we can offer the reduced rate of 2026 £945 / 2027 £965.

            You either can make a booking online or over the phone. Once we have your details, we’ll be able to check availability.

            • Tracing the River Thames from near its source all the way to Windsor
            • Didcot and its impressive railway heritage
            • The impressive Uffington White Horse & Dragon Hill
            • Beautiful wooded hills and green landscapes of the Chilterns
            • World famous Windsor Castle
            • Traditional pubs and award-winning English wines at the home of the Royal Regatta
            Photo Highlights Dates
            Self-Guided
            Self-Guided
            United Kingdom

            Cotswolds Explorer

            Self-Guided Leisure Cycling Holiday

            Duration

            8 days

            Prices from

            £1,395 P.P.
            View Reviews
            2
            1
            2
            3
            4
            5
            Grade 2-3: Gentle/Moderate
            More Info BOOK NOW

            Cotswolds Explorer

            Self-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.

            Daily departures available from April to mid October.

            Choose your own dates from:

            2026 £1395 per person

            2027 £1425 per person

            For a group of 4 or more we can offer the reduced rate of 2026 £1295 / 2027 £1325.

            You either can make a booking online or over the phone. Once we have your details, we’ll be able to check availability.

            • The famous Cotswolds market towns of Moreton-in-Marsh and Stow-on-the-Wold
            • Riverside relaxation in Bourton-on-the-Water, the “Venice of the Cotswolds”
            • Leisurely riding through beautiful rolling countryside
            • The historic village of Bibury, famous for its beautiful stone cottages
            • Cycling through charming chocolate box villages
            • Stately home of Blenheim Palace with 2000 acres of gardens and magnificent architecture
            Photo Highlights Dates
            Self-Guided
            Self-Guided
            Scotland

            Scotland - The Caledonia Way - Oban to Inverness

            Self-Guided Leisure Cycling Holiday

            Duration

            7 days

            Prices from

            £1,195 P.P.
            View Reviews
            2
            1
            2
            3
            4
            5
            Grade 3-4 : Moderate/Active
            More Info BOOK NOW

            Scotland - The Caledonia Way - Oban to Inverness

            Self-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.

            Start DateEnd DatePrice p.p.
            13/06/2026
            Guaranteed
            19/06/2026£1,195.00
            15/08/2026
            Fully Booked
            21/08/2026£1,195.00
            05/09/2026
            Fully Booked
            11/09/2026£1,195.00

            Daily departures (excluding Thursdays) available from April to mid October.

            Choose your own dates from:

            2026 £1495 per person

            2027 £1525 per person

            Alternatively for a great value holiday select one of our scheduled departures below.

            You can either make a booking online or over the phone. Once we have your details, we’ll be able to check availability.

            • Checking out Ben Nevis and The Grampians from Loch Linhe
            • Taking on the legendary ascent of Glendoe
            • Exploring Loch Ness and some of Scotland’s more remote National Scenic Areas, including the Appin Peninsula
            • Cycling Coast to Coast through Scotland’s best-loved towns including Oban, Fort William and Fort Augustus
            • Scenic ferry rides to the Ardgour peninsula
            • A chance to sample local whiskies at the Oban and Fort William distilleries
            Photo Highlights Dates
            Self-Guided
            Self-Guided
            United Kingdom

            NEW! UK - North York Moors, Coast and Abbeys - 5 Days Cycling

            Self-Guided Leisure Cycling Holiday

            Duration

            7 days

            Prices from

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

            NEW! UK - North York Moors, Coast and Abbeys - 5 Days Cycling

            Self-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. 

            Daily departures available from April to mid October.

            Choose your own dates from

            2026 £1095 per person

            2027 £1125 per person

            You can either make a booking online or over the phone. Once we have your details, we’ll be able to check availability.

            Please note that Scarborough and Whitby can be particularly busy in July and August, and hotels are less likely to have availability, so booking early is advised.

            • Scenic riding along the ‘The Cinder Track’ disused railway, with coastal views of Robin Hood’s Bay, Scarborough and Whitby
            • Riding up steep climbs and down exhilarating descents through beautiful heather moorlands on quiet roads in the North York Moors National Park
            • Tucking in to award-winning local fish & chips in Whitby harbour at the end of a long day in the saddle
            • Staying in the quaint historical Yorkshire towns and villages of Helmsley, Pickering and Great Ayton
            • The chance to visit an abundance of historic attractions including Whitby Abbey, Scarborough Castle and Rievaulx Abbey
            • Riding the serene forest tracks in Dalby Forest
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            Saddle Skedaddle staff were excellent. Consistently high standards delivered year on year. Don't think I'd trust anybody else when booking a cycling holiday!
            Susan, Slovenia - Capital to Coast, Leisure Cycling Holiday
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            This was the best of the several organised bike tours I've been on by light years, and I'm now looking at doing other tours with Skedaddle.
            Jay, France - St Malo to Nice, Road Cycling Holiday
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            Everything about the Skedaddle operation was spot-on, great attention to detail both before and during the trip. I was impressed by all things on the trip, quality of food, route briefings, accommodation, maps. I could go on!
            Paul, Land's End to John O'Groats Classic - 16 Days
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            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
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            From the first day to the last, everything was fantastic. We never had to worry about anything. Hotels, van pick-ups, guides - you had it all covered!
            Carol and Jim - Peru, Cycling Holiday
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            On 10+ trips with Skedaddle they have always delivered great trips and service. You get what you pay for and Skedaddle are very good at providing well run cycling holidays.
            Rob, Italy - Sardinia Island Flavours
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