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            Classic Cycling Challenges

            Don’t miss these classic cycling challenges, aimed at enabling the whole family to get some great miles in and conquer some of the most iconic cycling routes. An achievable challenge we guarantee will inspire the whole family!

            Designed with confident cyclists in mind, our range includes iconic classics such as the Coast to Coast, alongside place-to-place journeys in Europe. 

            • All Cycling Holidays
            • Classic Challenges
            Select Order Order By
            Supported
            Supported
            United Kingdom

            C2C - Coast to Coast

            Supported Leisure cycling holiday

            Duration

            5 days

            Prices from

            £855 P.P.
            View Reviews
            30
            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.

            Start DateEnd DatePrice p.p.
            30/05/2025
            Last Spaces
            03/06/2025£855.00
            11/07/2025
            Last Spaces
            15/07/2025£855.00
            19/09/2025
            Last Spaces
            23/09/2025£855.00
            • 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
            Self-Guided
            Self-Guided
            United Kingdom

            Hadrian's Cycleway (4 days cycling)

            Self-Guided Leisure Cycling Holiday

            Duration

            5 days

            Prices from

            £585 P.P.
            View Reviews
            11
            1
            2
            3
            4
            5
            Grade 2-3: Gentle/Moderate
            More Info BOOK NOW

            Hadrian's Cycleway (4 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.

            Start DateEnd DatePrice p.p.
            30/05/2025
            Guaranteed
            03/06/2025£585.00
            04/07/2025
            Guaranteed
            08/07/2025£585.00
            01/08/202505/08/2025£585.00

            Daily departures available from April to mid October.

            Choose your own dates from:

            2025 £685 per person

            2026 £725 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.

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

            • The sense of achievement having ridden from coast to coast
            • The well preserved forts of Birdoswald and Vindolanda
            • The rugged beauty of the North Pennines
            • The picturesque market town of Corbridge
            • Following in the footsteps of the Roman Empire
            • Flexibility to choose your own start date or one of our great value scheduled departure dates
            Photo Highlights Dates
            Self-Guided
            Self-Guided
            United Kingdom

            Hadrian's Cycleway (4 days cycling)

            Self-Guided Family Cycling Holiday

            Duration

            5 days

            Prices from

            £685 P.P.
            1
            2
            3
            4
            5
            Grade 2 - 3: Gentle/ Moderate
            More Info BOOK NOW

            Hadrian's Cycleway (4 days cycling)

            Self-Guided Family Cycling Holiday

            Daily departures available from April to mid October.

            Choose your own dates from:

            2025 £685 per person

            2026 £725 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 25% 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 25% discount for the children (subject to availability).

            • Cycling next to Hadrian’s Wall near Birdoswald
            • Seeing a live archaeological dig at Vindolanda
            • Beating your parents up one of the cheeky Skedaddle climbs
            • Corbridge and sinking a well-deserved pint of local ales 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
            Supported
            Supported
            United Kingdom

            Coast and Castles

            Supported Leisure Cycling Holiday

            Duration

            5 days

            Prices from

            £885 P.P.
            View Reviews
            8
            1
            2
            3
            4
            5
            Grade 3-4 : Moderate/Active
            More Info BOOK NOW

            Coast and Castles

            Supported Leisure Cycling Holiday

            Save £50

            Save £50 when you book onto our trip departing 16/07/2025 - Enter code FAV50 when you book. Discount applies to bookings made between 1 April 2025 and 8 May 2025 only. Ts and Cs apply.

            Start DateEnd DatePrice p.p.
            * 16/07/202520/07/2025£885.00
            03/09/202507/09/2025£885.00
            • Following the Tyne past the dramatic Tynemouth Priory
            • Cycling past the pristine dunes and sandy beaches at Druridge Bay
            • Stunning vistas as you approach imposing Bamburgh Castle
            • Glimpsing Edinburgh as you cycle from the Moorfoot Hills
            • The rugged beauty of the Scottish Borders
            Photo Highlights Dates
            Self-Guided
            Self-Guided
            Austria, Slovakia and Hungary

            Vienna to Budapest

            Self-Guided Leisure Cycling Holiday

            Duration

            8 days

            Prices from

            £1,145 P.P.
            View Reviews
            10
            1
            2
            3
            4
            5
            Grade 2-3: Gentle/Moderate
            More Info BOOK NOW

            Vienna to Budapest

            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 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.

            The season prices below are per person, and are applicable for all start dates between and inclusive of the stated dates.

            2025 29 Mar – 11 Oct

            Season 1 29 Mar – 10 Apr and 01 Oct – 11 Oct

            £1,145 – Sat Arrivals

            £1,295 – Mon, Tue, Wed, Thu, Fri and Sun Arrivals

            Season 2 11 Apr – 29 May and 05 – 30 Sep

            £1,285 – Fri, Sat and Sun Arrivals

            £1,425 – Mon, Tue, Wed and Thu Arrivals

            Season 3 30 May – 04 Sep

            £1,355 – Daily Arrivals

            • Spending your first evening in the iconic city of Vienna
            • The amazing views as you approach the Danube Bend
            • Exploring Bratislava
            • The imposing cathedral of Esztergom in Hungary
            • The sense of accomplishment as you finish the journey from Vienna to Budapest
            • Taking a thermal bath in beautiful Budapest
            Photo Highlights Dates
            Self-Guided
            Self-Guided
            Italy

            Lake Garda to Venice

            Self-Guided Leisure Cycling Holiday

            Duration

            8 days

            Prices from

            £1,775 P.P.
            View Reviews
            4
            1
            2
            3
            4
            5
            Grade 2: Gentle
            More Info BOOK NOW

            Lake Garda to Venice

            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. The season prices below are per person and are applicable for all start dates between and inclusive of the stated dates.

            2025 21 Apr – 29 Oct (excluding dates throughout July and August)

            Season 1 – £1775 21 Apr – 16 Jun and 03 Sep – 29 Oct

            Season 2 – £1995 17 Jun – 30 Jun and 01 – 02 Sep

            2026 18 Apr – 26 Oct (excluding dates throughout July and August)

            Season 1 – £1865 18 Apr – 14 Jun and 09 Sep – 26 Oct

            Season 2 – £2095 15 Jun – 30 Jun and 01 – 08 Sep

            If you‘re looking for a longer holiday, our Via Claudia route links into this tour perfectly; two self-guided tours of a similar grade that you‘re able to do back to back. Contact us if you’d like more info on this!

            To ensure you have the best experience possible, we’d recommend travelling in the Spring or in the Autumn. We don’t as standard offer this tour in the hotter, more humid, busier summer months of July and August. If however your dates are set in July or August, please call us for a chat and we’ll do what we can to accommodate you.

            • Enjoying a swim in Lake Garda
            • Cycling along Pellestrina Island surrounded by Venetian lagoons and fishing boats
            • Absorbing the hidden Rennaisance gems of the ‘belpaese’
            • Exploring Verona – a piece of art in itself
            • Discovering the medieval fortification of Montagnana
            • Taking a gondola ride along the canals of Venice
            Photo Highlights Dates
            Self-Guided
            Self-Guided
            United Kingdom

            C2C - Coast to Coast (5 Days Cycling)

            Self-Guided Leisure Cycling Holiday

            Duration

            6 days

            Prices from

            £875 P.P.
            View Reviews
            6
            1
            2
            3
            4
            5
            Grade 3 : Moderate
            More Info BOOK NOW

            C2C - Coast to Coast (5 Days Cycling)

            Self-Guided Leisure Cycling Holiday

            Start DateEnd DatePrice p.p.
            09/05/2025 (Penrith)
            Contact Us
            14/05/2025£875.00
            23/05/2025 (Newcastle)
            Guaranteed
            28/05/2025£875.00
            27/06/2025 (Penrith)
            Guaranteed
            02/07/2025£875.00
            18/07/2025 (Newcastle)
            Guaranteed
            23/07/2025£875.00
            08/08/2025 (Penrith)13/08/2025£875.00
            15/08/2025 (Newcastle)20/08/2025£875.00
            29/08/2025 (Newcastle)03/09/2025£875.00
            05/09/2025 (Penrith)10/09/2025£875.00

            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:

            2025 £995 per person

            2026 £1045 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.

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

            • 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
            Self-Guided
            Self-Guided
            Austria, Slovakia and Hungary

            Vienna to Budapest

            Self-Guided Family Cycling Holiday

            Duration

            8 days

            Prices from

            £1,145 P.P.
            1
            2
            3
            4
            5
            Grade 2 - 3: Gentle/ Moderate
            More Info BOOK NOW

            Vienna to Budapest

            Self-Guided Family Cycling Holiday

            Child Discounts

            The season prices below are per person, and are applicable for all start dates between and inclusive of the stated dates.

            The season prices below are per person, and are applicable for all start dates between and inclusive of the stated dates.

            2025 29 Mar – 11 Oct

            Season 1 29 Mar – 10 Apr and 01 Oct – 11 Oct

            £1,145 – Sat Arrivals

            £1,295 – Mon, Tue, Wed, Thu, Fri and Sun Arrivals

            Season 2 11 Apr – 29 May and 05 – 30 Sep

            £1,285 – Fri, Sat and Sun Arrivals

            £1,425 – Mon, Tue, Wed and Thu Arrivals

            Season 3 30 May – 04 Sep

            £1,355 – Daily Arrivals

            The following children’s discounts are available off the land-only price:

            0 – 5 – Free

            6 – 11 – 50%

            12 – 14 – 25%

            15 – 17 – 10%.

            Available if sharing a room with 2 fully-paying passengers / dependent on availability.

            • Spending your first evening in the iconic city of Vienna
            • The amazing views as you approach the Danube Bend
            • Exploring Bratislava
            • The imposing cathedral of Esztergom in Hungary
            • The sense of accomplishment as you finish the journey from Vienna to Budapest
            • Taking a thermal bath in beautiful Budapest
            Photo Highlights Dates
            Self-Guided
            Self-Guided
            Italy

            Lake Garda to Venice

            Self-Guided Family Cycling Holiday

            Duration

            8 days

            Prices from

            £1,775 P.P.
            1
            2
            3
            4
            5
            Grade 2 : Gentle
            More Info BOOK NOW

            Lake Garda to Venice

            Self-Guided Family Cycling Holiday

            Child Discounts

            Daily departures available. The season prices below are per person and are applicable for all start dates between and inclusive of the stated dates.

            2025 21 Apr – 29 Oct (excluding dates throughout July and August)

            Season 1 – £1775 21 Apr – 16 Jun and 03 Sep – 29 Oct

            Season 2 – £1995 17 Jun – 30 Jun and 01 – 02 Sep

            2026 18 Apr – 26 Oct (excluding dates throughout July and August)

            Season 1 – £1865 18 Apr – 14 Jun and 09 Sep – 26 Oct

            Season 2 – £2095 15 Jun – 30 Jun and 01 – 08 Sep

            We can offer the following discounts for children under 18:

            We can offer a 20% discount for any child under 18 travelling with 2 fully-paying passengers. If you’re happy to share a family room (where available) we can often offer an additional 10% – please chat to our team about your preferred rooming arrangements.

            To ensure you have the best experience possible, we’d recommend travelling in the Spring or in the Autumn. We don’t as standard offer this tour in the hotter, more humid, busier summer months of July and August. If however your dates are set in July or August, please call us for a chat and we’ll do what we can to accommodate you.

            • Enjoying a swim in Lake Garda
            • Cycling along Pellestrina Island surrounded by Venetian lagoons and fishing boats
            • Absorbing the hidden Rennaisance gems of the ‘belpaese’
            • Exploring Verona – a piece of art in itself
            • Discovering the medieval fortification of Montagnana
            • Taking a gondola ride along the canals of Venice
            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

            £995 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

            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:

            2025 £995 per person

            2026 £1045 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.

            Kid’s Discounts

            For children below the age of 18 who are travelling with 2 full-paying passengers, we are able to offer a 25% 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 25% 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
            Quote
            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
            Quote
            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
            Quote
            One of the very best trips! The kindness and professionalism of the lead guide and his locally based colleagues was outstanding in every respect.
            Brenda, Italy - Dolomites of Brenta, Guided Mountain Bike Holiday
            Quote
            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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