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          Skedaddle Classics, Your Way

          Are you in search of a cycling tour that's specifically designed for you and your family or friends? Look no further than our exclusive collection of cycle tours, tailor-made to fulfill your dream cycling experience and shared only with those who matter most.

          To get you started, we've hand-picked some of our best-loved cycle tours, all set in destinations known like the back of our local teams' hands. With their vast local knowledge and expertise, we offer unparalleled flexibility to cater to your unique needs. From adjusting the number of cycling days to bike hire, support level, accommodation, and more – we can customize it all according to your preferences.

          Simply explore the tailor-made itineraries below, send us an enquiry mentioning your preferred trip and your priorities. Leave the rest to us, so you can sit back and savor the journey. Alternatively, visit our dedicated Tailor Made page to discover how we can turn your dream trip into a wonderful reality!

          • All Cycling Holidays
          • Skedaddle Classics your way

          Page 1 of 3

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

          C2C - Coast to Coast (3 Days Cycling)

          Self-Guided Leisure Bike Tour

          Duration

          4 days

          Prices from

          $850 P.P.
          View Reviews
          3
          1
          2
          3
          4
          5
          Grade 4 : Active
          More Info BOOK NOW

          C2C - Coast to Coast (3 Days Cycling)

          Self-Guided Leisure Bike Tour

          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.
          21/05/2027 (Newcastle)24/05/2027$850.00
          18/06/2027 (Penrith)21/06/2027$850.00
          09/07/2027 (Newcastle)12/07/2027$850.00
          23/07/2027 (Penrith)26/07/2027$850.00
          20/08/2027 (Newcastle)23/08/2027$850.00
          17/09/2027 (Newcastle)20/09/2027$850.00

          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:

          2027 $1065 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.

          Due to The Great North Run in Newcastle in September 2027, it’s not possible to start this tour in Newcastle between the 10th and 12th Sep, but do chat to us if you have set dates, as we can likely organise a Penrith start for you.

          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
          • Flexibility to choose your own start date or one of our great value scheduled departure dates
          • Suitable for adults and older children
          Photo Highlights Dates
          Self-Guided
          Self-Guided
          United Kingdom

          C2C - Coast to Coast (4 Days Cycling)

          Self-Guided Leisure Bike Tour

          Duration

          5 days

          Prices from

          $1,110 P.P.
          View Reviews
          15
          1
          2
          3
          4
          5
          Grade 3 : Moderate
          More Info BOOK NOW

          C2C - Coast to Coast (4 Days Cycling)

          Self-Guided Leisure Bike Tour

          Start DateEnd DatePrice p.p.
          21/05/2027 (Newcastle)25/05/2027$1,110.00
          18/06/2027 (Penrith)22/06/2027$1,110.00
          09/07/2027 (Newcastle)13/07/2027$1,110.00
          23/07/2027 (Penrith)27/07/2027$1,110.00
          20/08/2027 (Newcastle)24/08/2027$1,110.00
          17/09/2027 (Newcastle)21/09/2027$1,110.00

          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:

          2027 $1310 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.

          Due to The Great North Run in Newcastle in September 2027, it’s not possible to start this tour in Newcastle between the 10th and 12th Sep, but do chat to us if you have set dates, as we can likely organise a Penrith start for you.

          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 mouthwatering breakfasts
          • Flexibility to choose your own start date or one of our great value scheduled departure dates
          • Suitable for adults and older children
          Photo Highlights Dates
          Self-Guided
          Self-Guided
          United Kingdom

          C2C - Coast to Coast (5 Days Cycling)

          Self-Guided Leisure Bike Tour

          Duration

          6 days

          Prices from

          $1,310 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 Bike Tour

          Start DateEnd DatePrice p.p.
          21/05/2027 (Newcastle)26/05/2027$1,310.00
          18/06/2027 (Penrith)23/06/2027$1,310.00
          09/07/2027 (Newcastle)14/07/2027$1,310.00
          23/07/2027 (Penrith)28/07/2027$1,310.00
          20/08/2027 (Newcastle)25/08/2027$1,310.00
          17/09/2027 (Newcastle)22/09/2027$1,310.00

          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:

          2027 $1525 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.

          Due to The Great North Run in Newcastle in September 2027, it’s not possible to start this tour in Newcastle between the 10th and 12th Sep, but do chat to us if you have set dates, as we can likely organise a Penrith start for you.

          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
          United Kingdom

          C2C - Coast to Coast (5 Days Cycling)

          Self-Guided Family Bike Tour

          Duration

          6 days

          Prices from

          $1,525 P.P.
          1
          2
          3
          4
          5
          Grade 3 : Moderate
          More Info BOOK NOW

          C2C - Coast to Coast (5 Days Cycling)

          Self-Guided Family Bike Tour

          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:

          2027 $1525 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.

          Due to The Great North Run in Newcastle in September 2027, it’s not possible to start this tour in Newcastle between the 10th and 12th Sep, but do chat to us if you have set dates, as we can likely organise a Penrith start for you.

          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
          Self-Guided
          Self-Guided
          Italy

          Tuscany - Giro della Toscana

          Self-Guided Road Bike Tour

          Duration

          8 days

          Prices from

          $2,565 P.P.
          View Reviews
          4
          1
          2
          3
          4
          5
          Grade 3: Moderate
          More Info BOOK NOW

          Tuscany - Giro della Toscana

          Self-Guided Road Bike Tour

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

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

          Season 1 – $2565 29 Mar – 14 Jun and 09 Sep – 26 Oct

          Season 2 – $2995 15 – 30 Jun and 01 – 08 Sep

          2027 30 Mar – 26 Oct (excluding dates in July and August)

          Season 1 – $2695 30 Mar – 14 Jun and 09 Sep – 26 Oct

          Season 2 – $3135 15 – 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.

          • Cycling through the historic wine regions of Tuscany, stopping off for a bit of wine tasting along the way
          • Staying in quality accommodation, with fantastically warm hospitality
          • Easing along the rolling hills of the ‘Colli Sienesi’
          • Riding the stunning UNESCO heritage region of Val d’Orcia
          • Stopping off at the lovely San Gimignano and Montalcino
          • Chilling out with a post-ride Chianti
          Photo Highlights Dates
          Self-Guided
          Self-Guided
          Italy

          Classic Tuscany

          Self-Guided Leisure Bike Tour

          Duration

          8 days

          Prices from

          $2,235 P.P.
          View Reviews
          7
          1
          2
          3
          4
          5
          Grade 3 : Moderate
          More Info BOOK NOW

          Classic Tuscany

          Self-Guided Leisure Bike Tour

          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.
          05/05/202712/05/2027$2,235.00
          24/09/202701/10/2027$2,235.00

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

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

          Season 1 – $2425 29 Mar – 14 Jun and 09 Sep – 26 Oct

          Season 2 – $2850 15-30 Jun and 01-08 Sep

          2027 30 Mar – 26 Oct (excluding dates throughout July and August)

          Season 1 – $2535 30 Mar – 14 Jun and 09 Sep – 26 Oct

          Season 2 – $2995 15-30 Jun and 01-08 Sep

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

          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.

          • Staying at Tuscan farms overlooking stunning countryside
          • Visiting the famous towns of Monteriggioni, Buonconvento, Asciano and Siena
          • Riding through wonderful landscapes, wide open fields, cypress-lined hills and vineyards
          • Trying delicious, regional dishes
          • Sampling the best wines of Chianti, Montepulciano and Montalcino
          • Absorbing the atmosphere of San Gimignano – a UNESCO World Heritage Site
          Photo Highlights Dates
          Self-Guided
          $125 OFF
          Self-Guided
          Italy

          Tuscany - Sacred Routes

          Self-Guided Mountain Bike Tour

          Duration

          8 days

          Prices from

          $2,565 P.P.
          View Reviews
          4
          1
          2
          3
          4
          5
          Grade 3 - 4: Moderate/ Challenging
          More Info BOOK NOW

          Tuscany - Sacred Routes

          Self-Guided Mountain Bike Tour

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

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

          Season 1 – $2565 29 Mar – 14 Jun and 09 Sep – 26 Oct

          Season 2 – $2850 15 Jun – 30 Jun and 01 – 08 Sep

          2027 30 Mar – 26 Oct (excluding dates throughout July and August)

          Season 1 – *$2695 30 Mar – 14 Jun and 09 Sep – 26 Oct

          Season 2 – *£2995 15 – 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.

          • Staying in lovely Tuscan accommodation overlooking stunning landscapes
          • Riding the Montagnola trails, the location of a well-known Sienese MTB race
          • Sampling the best wines of Chianti, Montepulciano and Montalcino
          • Riding down the “Crete Senesi” on a roller coaster ridge ride
          • Enjoying the journey across Tuscany on a variety of terrain
          • Visiting the famous hilltop towns of San Gimignano, Monteriggioni, San Quirico d‘Orcia and Pienza
          Photo Highlights Dates
          Self-Guided
          Self-Guided
          Italy

          Tuscany - Pisa to Florence

          Self-Guided Leisure Bike Tour

          Duration

          8 days

          Prices from

          $1,850 P.P.
          View Reviews
          6
          1
          2
          3
          4
          5
          Grade 2-3: Gentle/ Moderate
          More Info BOOK NOW

          Tuscany - Pisa to Florence

          Self-Guided Leisure Bike Tour

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

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

          Season 1 – $1850 29 Mar – 14 Jun and 09 Sep – 26 Oct

          Season 2 – $2135 15 – 30 Jun and 01 – 08 Sep

          2027 30 Mar – 26 Oct (excluding dates throughout July and August)

          Season 1 – $1935 30 Mar – 14 Jun and 09 Sep – 26 Oct

          Season 2 – $2235 15 – 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.

          • Riding between two of Italy’s most iconic cities
          • Exploring Pisa, home of the world-famous Piazza dei Miracoli
          • Cycling along quiet country lanes through Tuscan countryside
          • Cycling past fairy tale Renaissance palaces and villas
          • Visiting Vinci, the birthplace of Leonardo da Vinci
          • Spending a free day in Florence, the birthplace of the Renaissance
          Photo Highlights Dates
          Guided
          Guided
          Spain

          Sierras Explorer

          Guided Mountain Bike Tour

          Duration

          7 days

          Prices from

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

          Sierras Explorer

          Guided Mountain Bike Tour

          E-MTB HIRE AVAILABLE

          This holiday is great fun on a regular mountain bike or an e-mountain bike and you can choose to hire either when you book your holiday with us! If you’re an experienced rider, you can choose one of our quality e-mountain hire bikes and experience the buzz of a pedal-assisted ride. Select your e-MTB hire when you book a holiday with us. Bear in mind that the pace will be set to riders with a regular mountain bike.

          Start DateEnd DatePrice p.p.
          31/10/2026
          Guaranteed
          06/11/2026$2,995.00
          • Exploring the historical town of Ronda
          • Riding the slick Guadiaro single-track
          • Incredible descent through the Alcornocales to the white hilltop of Jimena
          • Spending a night in the beautiful setting of a 13th century Moorish castle
          • Riding the shores of the Straits of Gibraltar past secluded coves and ancient watchtowers
          • Tapas bar hopping in the fun filled town of Tarifa
          Photo Highlights Dates
          Self-Guided
          $95 OFF
          Self-Guided
          Spain

          Sierras Explorer

          Self-Guided Mountain Bike Tour

          Duration

          7 days

          Prices from

          $2,210 P.P.
          View Reviews
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          Grade 3 : Moderate
          More Info BOOK NOW

          Sierras Explorer

          Self-Guided Mountain Bike Tour

          E-MTB HIRE AVAILABLE

          This holiday is great fun on a regular mountain bike or an e-mountain bike and you can choose to hire either when you book your holiday with us! If you’re an experienced rider, you can choose one of our quality e-mountain hire bikes and experience the buzz of a pedal-assisted ride. Select your e-MTB hire when you book a holiday with us. Bear in mind that the pace will be set to riders with a regular mountain bike.

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

          2026 01 Mar- 30 Nov (excluding dates from 29 Mar – 04 Apr / 01 Jul to 07 Sep)

          Season 1 – $2210 01 – 28 Mar / 01 Oct – 30 Nov

          Season 2 – $2425 05 – 30 Apr / 03 May – 30 Jun / 08 – 30 Sep

          2027 01 Mar – 30 Nov (excluding dates in July & August)

          Season 1 – $2250 01 – 18 Mar / 01 Oct – 30 Nov

          Season 2 – $2565 29 Mar – 29 Apr / 03 May – 30 Jun / 14 – 30 Sep

          • Exploring the historical town of Ronda
          • Riding the slick Guadiaro single-track
          • The incredible descent through the Alcornocales to the white hilltop town of Jimena
          • Spending a night in the beautiful setting of a 13th century Moorish castle.
          • Riding the shores of the Straits of Gibraltar past secluded coves and ancient watchtowers
          • Tapas bar hopping in the fun-filled town of Tarifa
          Photo Highlights Dates
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          • Next page

          Not sure which trip's right for you? Just ask!

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

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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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