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            Classic Destinations

            Some destinations simply must be ticked off the bucket list! That’s why we’ve developed a range of trips in locations that we feel are synonymous with cycling.

            Whether you’re a foodie looking for local wine tasting opportunities, or after stunning scenery from the saddle, all of our holidays featured offer an abundance of amazing culture and fantastic landscapes. This is your chance to explore some of the world’s most famed destinations in the best way possible.

            • All Cycling Holidays
            • Classic Destinations

            Page 1 of 4

            Select Order Order By
            Self-Guided
            Self-Guided
            Spain

            Bilbao to San Sebastian

            Self-Guided Leisure Cycling Holiday

            Duration

            7 days

            Prices from

            £1,365 P.P.
            View Reviews
            2
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            Grade 3 : Moderate
            More Info BOOK NOW

            Bilbao to San Sebastian

            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.

            Start DateEnd DatePrice p.p.
            31/05/202506/06/2025£1,365.00
            21/06/202527/06/2025£1,625.00
            27/09/202503/10/2025£1,625.00

            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 01 Apr – 31 Oct (excluding dates from 01 – 31 Aug)

            Season 1 – £1595 01 – 11 Apr / 05 – 31 May / 1 – 31 Oct

            Season 2 – £1855 20 – 30 Apr / 01 Jun – 31 Jul / 01 – 11 Sep / 22 – 30 Sep

            2026 06 Apr – 31 Oct (excluding dates from 01 – 31 Aug and 11 – 20 Sep)

            Season 1 – £1645 06 – 29 Apr / 03 May – 11 Jun / 1 – 31 Oct

            Season 2 – £1915 30 Apr – 02 May / 12 Jun – 31 Jul / 01 – 10 Sep / 21 – 30 Sep

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

            • Visiting the world-class Guggenheim museum
            • Savouring fabulous Basque cuisine
            • Cycling through the beautiful Urdaibai natural park
            • Admiring the dramatic Atlantic coastline: Cliffs, beaches, estuaries and coves
            • Relaxing by the harbour of the picturesque fishing village of Lekeitio
            • Arriving in stunning San Sebastian and bar hopping in the Casco Viejo
            Photo Highlights Dates
            Self-Guided
            Self-Guided
            Italy

            Emilia-Romagna - The Food Valley

            Self-Guided Leisure Cycling Holiday

            Duration

            8 days

            Prices from

            £1,495 P.P.
            View Reviews
            4
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            Grade 2-3: Gentle/Moderate
            More Info BOOK NOW

            Emilia-Romagna - The Food Valley

            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.

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

            2025 24 Mar – 29 Oct (excluding dates throughout July and August)

            Season 1 – £1495 24 Mar – 16 Jun and 03 Sep – 29 Oct

            Season 2 – £1645 17 Jun – 30 Jun and 01 – 02 Sep

            2026 29 Mar – 26 Oct (excluding dates throughout July and August)

            Season 1 – £1575 29 Mar – 14 Jun and 09 Sep – 26 Oct

            Season 2 – £1735 15 Jun – 30 Jun and 01 – 08 Sep

            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.

            • Gently cycling on quiet roads and cycle paths through beautiful countryside
            • Sampling tasty slow-food produce on the Food Valley Bike route from Cremona to Parma
            • Tasting authentic Italian food in their towns of origin such as Parma Ham, Parmigiano Reggiano, Balsamic Vinegar, and Bolognese Ragù
            • Visiting the hometown of the famous Italian composer Giuseppe Verdi
            • Exploring modern and bustling Modena
            • Taking in the vibrant university city of Bologna
            Photo Highlights Dates
            Self-Guided
            Self-Guided
            Ireland

            Highlights of Kerry

            Self-Guided Leisure Cycling Holiday

            Duration

            8 days

            Prices from

            £1,495 P.P.
            View Reviews
            1
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            Grade 3-4 : Moderate/Active
            More Info BOOK NOW

            Highlights of Kerry

            Self-Guided Leisure Cycling Holiday

            E-BIKE HIRE AVAILABLE

            This holiday is well-suited to both normal 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 01 Apr to 10 Oct.

            2025 £1495 per person.

            • Cycling the foothills of Ireland’s highest Mountain – Carrantuohill
            • Exploring the picturesque shores of Kells Bay
            • Dining in cosy Irish Pubs
            • Enjoying views over the spectacular Three Lakes of Killarney
            • Riding through the renowned Gap of Dunloe
            • Visiting Valentia Island and discovering 360-million-year-old Tetrapod footprints.
            Photo Highlights Dates
            Self-Guided
            Self-Guided
            Italy

            Sicily

            Self-Guided Leisure Cycling Holiday

            Duration

            8 days

            Prices from

            £1,675 P.P.
            View Reviews
            1
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            Grade 2: Gentle
            More Info BOOK NOW

            Sicily

            Self-Guided Leisure Cycling Holiday

            E-BIKE HIRE AVAILABLE

            This holiday is well-suited to both normal 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. The season prices below are per person, and applicable for all start dates between and inclusive of the stated dates.

            2025 24 Mar – 29 Oct (excluding departures from 09 Jun – 31 August)

            Season 1 – £1675 24 Mar – 08 Jun and 09 Sep – 29 Oct

            Season 2 – £1895 01 Sep – 08 Sep

            2026 29 Mar – 26 Oct (excluding departures from 08 Jun – 31 August)

            Season 1 – £1765 29 Mar – 07 Jun and 09 Sep – 26 Oct

            Season 2 – £1995 01 Sep – 08 Sep

            • Visiting the Baroque towns of Modica, Ragusa and Noto, all UNESCO Heritage Sites
            • Sampling delicious Sicilian pastries, like cannoli
            • Cycling along the beautiful coastal road to Capo Passero
            • Exploring the medieval streets of Ortigia di Siracusa
            • Enjoying an aperitivo ‘al fresco’ with the locals in one of the many piazzas
            • Discovering the astonishing Oasis of Vendicari
            Photo Highlights Dates
            Self-Guided
            Self-Guided
            United Kingdom

            Way of the Roses (5 days cycling)

            Self-Guided Leisure Cycling Holiday

            Duration

            6 days

            Prices from

            £895 P.P.
            View Reviews
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            Grade 3 : Moderate
            More Info BOOK NOW

            Way of the Roses (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.  

            Start DateEnd DatePrice p.p.
            08/06/202513/06/2025£895.00
            13/07/2025
            Guaranteed
            18/07/2025£895.00
            10/08/2025
            Guaranteed
            15/08/2025£895.00
            14/09/202519/09/2025£895.00

            Daily departures (excl. Thu and Fri) available from April to mid October.

            Choose your own dates from:

            2025 £1195 per person

            2026 £1255 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.

            • Eric Morecambe’s statue on Morecambe waterfront
            • Cycling through the Forest of Bowland and the Yorkshire Dales
            • Yorkshire ales and great pub food
            • York – flat cycling, big Minster
            • The Wolds, chalky rolling hills, with big country views
            • Fish & chips on Bridlington’s waterfront to celebrate your achievement!
            Photo Highlights Dates
            Self-Guided
            Self-Guided
            Italy

            Prosecco To The Sea

            Self-Guided Leisure Cycling Holiday

            Duration

            7 days

            Prices from

            £1,135 P.P.
            View Reviews
            2
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            Grade 2: Gentle
            More Info BOOK NOW

            Prosecco To The Sea

            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.

            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 (no departures in July and August)

            Season 1 – £1135 21 Apr – 16 Jun and 03 Sep – 29 Oct

            Season 2 – £1195 17 Jun – 30 Jun and 01 – 02 Sep

            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.

            • Scenic cycling in the UNESCO vineyards of Prosecco
            • Plenty of opportunities for wine tasting at the end of a day’s ride
            • Superb regional cuisine served on terraces overlooking vineyards
            • Pretty medieval towns and historic castles
            • Riding close to Venice Lagoon
            • Dipping your toes in the Adriatic sea
            Photo Highlights Dates
            Self-Guided
            Self-Guided
            Spain

            Andalucia - White Villages to the Ocean

            Self-Guided Leisure Cycling Holiday

            Duration

            7 days

            Prices from

            £1,245 P.P.
            View Reviews
            3
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            Grade 3 : Moderate
            More Info BOOK NOW

            Andalucia - White Villages to the Ocean

            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.
            18/05/202524/05/2025£1,245.00
            21/09/202527/09/2025£1,275.00
            12/10/2025
            Guaranteed
            18/10/2025£1,275.00

            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 01 Mar – 30 Nov (excluding dates from 01 Jul to 13 Sep)

            Season 1 – £1495 01 Mar – 11 Apr and 1 – 30 Nov

            Season 2 – £1545 05 – 07 May, 12 May – 30 Jun and 15 – 30 Oct

            Season 3 – £1595 20 – 30 Apr and 14 Sep – 14 Oct

            2026 01 Mar – 30 Nov (excluding dates from 01 Jul to 05 Sep)

            Season 1 – £1535 01 – 28 Mar and 1 – 30 Nov

            Season 2 – £1595 06 – 30 Apr, 01 – 30 Jun and 15 – 30 Oct

            Season 3 – £1645 03 – 31 May and 07 Sep – 14 Oct

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

            • Exploring the historical town of Ronda, surrounded by the stunning Sierras
            • Discovering beautiful Grazalema, nestled below atmospheric, limestone mountains
            • Descending from the Puerto Boyar out of the awe-inspiring Grazalema Natural Park
            • Sipping local sherries in the rustic bodegas of Arcos
            • Cycling alongside the white, sandy beaches of the Costa de la Luz; the Coast of Light
            • Hopping between tapas bars in the fun-filled town of Conil
            Photo Highlights Dates
            Supported
            Supported
            United Kingdom

            Way of the Roses

            Supported Leisure Cycling Holiday

            Duration

            6 days

            Prices from

            £1,035 P.P.
            View Reviews
            2
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            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.
            22/06/2025
            Guaranteed
            27/06/2025£1,035.00
            07/09/2025
            Guaranteed
            12/09/2025£1,035.00
            26/09/202501/10/2025£1,035.00
            • 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
            Supported
            Supported
            United Kingdom

            Coast and Castles

            Supported Leisure Cycling Holiday

            Duration

            5 days

            Prices from

            £885 P.P.
            View Reviews
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            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
            Supported
            Supported
            United Kingdom

            Hadrian's Cycleway

            Supported Leisure cycling holiday

            Duration

            6 days

            Prices from

            £995 P.P.
            View Reviews
            15
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            Grade 3 : Moderate
            More Info BOOK NOW

            Hadrian's Cycleway

            Supported Leisure cycling holiday

            Save £50

            Save £50 when you book onto our trip departing 06/06/2025 - 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.
            * 06/06/2025 E-Bike Departure
            Guaranteed
            11/06/2025£995.00
            22/08/2025
            Fully Booked
            27/08/2025£995.00
            • 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
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            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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            News, Reviews & Stories

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            To help you plan, we wanted to look at some of the trends we believe will go the extra mile...

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