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          Road Cycling Journeys

          We found 19 Holidays in your search for:

          Destinations (74)
          Types of Cycling / Grades (1)
          Departure Month

          2025

          2026

          2027

          Level of Support

          We found 19 Holidays in your search for:

          Select Order Order By
          Destinations (74)
          Types of Cycling / Grades (1)
          Departure Month

          2025

          2026

          2027

          Level of Support

          Our road cycling journeys are designed to bring together two of our favourite loves; cycling and travelling. These journeys have been tailor-made to maximise your cycling experience whilst also feeding your travel bug, visiting multiple locations and seeing all the sights.

          Find out more about our road cycling journeys and how you can join in below.

          • All Cycling Holidays
          • All Road Cycling Tours
          • Place To Place Journeys

          Page 2 of 2

          Select Order Order By
          Guided
          Guided
          Spain

          Sierra Nevada and Granada

          Guided Road Bike Tour

          Duration

          7 days

          Prices from

          $2,835 P.P.
          View Reviews
          1
          1
          2
          3
          4
          5
          Grade 3 - 4: Moderate/ Challenging
          More Info BOOK NOW

          Sierra Nevada and Granada

          Guided Road Bike Tour

          Start DateEnd DatePrice p.p.
          03/05/2026
          Guaranteed
          09/05/2026$2,835.00
          18/10/202624/10/2026$2,835.00
          • Checking out the white mountain villages of the Alpujarras
          • A night in a luxurious cave house in Guadix
          • The Sierra Nevada Challenge – riding to the roof of Spain
          • The classic Vuelta ride through the Sierra de Pandera
          • Tasty tapas and sunset sangrias
          • The descent to Granada and its amazing Alhambra Palace
          Photo Highlights Dates
          Guided
          Guided
          Spain

          Basque Country to Andalucia Classic - North to South

          Guided Road Bike Tour

          Duration

          16 days

          Prices from

          $5,905 P.P.
          View Reviews
          21
          1
          2
          3
          4
          5
          Grade 4: Challenging
          More Info BOOK NOW

          Basque Country to Andalucia Classic - North to South

          Guided Road Bike Tour

          Start DateEnd DatePrice p.p.
          10/04/202625/04/2026$5,905.00
          27/09/202612/10/2026$5,905.00
          • Cycling through the varied beauty of 14 national parks
          • Delicious regional dishes which change from day to day as you traverse the entire country
          • Crossing the granite Guadarrama and Gredos mountain ranges as you move from the north to the south of the country
          • Views over the Straits of Gibraltar to Morocco
          • The beautiful towns of San Sebastian, Guadaloupe and Ronda
          • The satisfaction of arriving in to Tarifa with over 1,000 miles of Spanish roads having passed beneath your wheels
          Photo Highlights Dates
          Guided
          Guided
          Spain

          Basque Country to Andalucia Explorer - North to South

          Guided Road Bike Tour

          Duration

          21 days

          Prices from

          $7,420 P.P.
          View Reviews
          1
          1
          2
          3
          4
          5
          Grade 3: Moderate
          More Info BOOK NOW

          Basque Country to Andalucia Explorer - North to South

          Guided Road Bike Tour

          Start DateEnd DatePrice p.p.
          10/05/202630/05/2026$7,420.00
          30/08/2026
          Guaranteed
          19/09/2026$7,420.00
          • Starting in style with a Pintxos tour in elegant San Sebastian
          • Cycling through the vineyards & dramatic mountains of Rioja
          • Spending an evening in the Monastery of Valvanera
          • Seduced by Segovia with its castle and cathedral
          • Descending from the Sierras to the charming beauty of Cordoba
          • Finishing your ride in style at the fun loving city of Malaga-
          Photo Highlights Dates
          Guided
          Guided
          France

          St Malo to Nice Explorer

          Guided Road Bike Tour

          Duration

          20 days

          Prices from

          $8,420 P.P.
          View Reviews
          19
          1
          2
          3
          4
          5
          Grade 3: Moderate
          More Info BOOK NOW

          St Malo to Nice Explorer

          Guided Road Bike Tour

          Start DateEnd DatePrice p.p.
          11/05/2026
          Guaranteed
          30/05/2026$8,420.00
          07/09/202626/09/2026$8,420.00
          • Cycling along the Brittany coast with views out to the Abbey of Mont St-Michel
          • Travelling under your own power all the way from the Channel to the Mediterranean
          • Meandering along the Loire, Dordogne and Rhône rivers
          • Riding through vineyards of Chateauneuf-du-pape
          • Riding through the lavender fields of Provence and winding your way through the Verdon Gorge
          • Descending to Nice to ride along the Promenade des Anglais
          Photo Highlights Dates
          Guided
          Guided
          Italy

          Coast to Coast - L'Adriatico al Tirreno

          Guided Road Bike Tour

          Duration

          9 days

          Prices from

          $3,850 P.P.
          View Reviews
          10
          1
          2
          3
          4
          5
          Grade 3: Moderate
          More Info BOOK NOW

          Coast to Coast - L'Adriatico al Tirreno

          Guided Road Bike Tour

          Start DateEnd DatePrice p.p.
          16/05/202624/05/2026$3,850.00
          12/09/2026
          Guaranteed
          20/09/2026$3,850.00
          • An epic coast to coast journey riding all the way from the Adriatic coast to the Tyrrhenian Sea
          • Cycling through the smallest republic in Europe, San Marino
          • Easing along the rolling Nove Colli hills, the routes of the famous Italian Gran Fondo
          • Visiting historical sites such as the Palazzo Ducale in Orvieto and San Francis Abbey in Assisi
          • Staying in quality accommodation, with fantastically warm hospitality
          • Riding to Gubbio and Assisi, UNESCO World Heritage sites
          Photo Highlights Dates
          Self-Guided
          Self-Guided
          Spain

          Bilbao to Santiago

          Self-Guided Road Bike Tour

          Duration

          10 days

          Prices from

          $2,910 P.P.
          1
          2
          3
          4
          5
          Grade 3: Moderate
          More Info BOOK NOW

          Bilbao to Santiago

          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 05 Apr – 31 Oct

          Season 1 – $2935 03 – 31 May / 29 Sep – 31 Oct

          Season 2 – $3235 01 Jun – 31 Jul / 01 – 28 Sep

          Season 3 – $3650 05 – 30 Apr / 01 – 31 Aug

          • Riding along the stunning and dramatic Cantabrian coastline
          • A stunning start in the Basque city of Bilbao
          • Enjoying a fabulous seafood platter in San Vicente de Barquera
          • Pouring cider in the old town of Oviedo
          • Arriving at the roof of the ‘Camino Primitivo‘, Puerto Palo
          • Cycling through beautiful, rural, enchanting Galicia to arrive in historical Santiago to collect a pilgrims’ certificate
          Photo Highlights Dates
          Guided
          Guided
          Scotland

          Scotland - Kirkpatrick Coast to Coast

          Guided Road Bike Tour

          Duration

          6 days

          Prices from

          $1,895 P.P.
          View Reviews
          4
          1
          2
          3
          4
          5
          Grade 3: Moderate
          More Info BOOK NOW

          Scotland - Kirkpatrick Coast to Coast

          Guided Road Bike Tour

          Start DateEnd DatePrice p.p.
          10/05/202615/05/2026$1,895.00
          19/07/202624/07/2026$1,895.00
          13/09/202618/09/2026$1,895.00
          • Learn about Kirkpatrick Macmillan and his velocipede, which changed the world forever!
          • Breathtaking landscapes and dramatic coastlines
          • Charming and vibrant Kirkcudbright
          • Victorian viaducts and romantic ruined abbeys
          • Picturesque finish at the harbour of Eyemouth
          • Quiet country roads of the unexplored Borders
          Photo Highlights Dates
          Guided
          Guided
          Italy

          Coast to Coast - Puglia to Cilento

          Guided Road Bike Tour

          Duration

          8 days

          Prices from

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

          Coast to Coast - Puglia to Cilento

          Guided Road Bike Tour

          Start DateEnd DatePrice p.p.
          18/04/202625/04/2026$2,995.00
          26/04/202603/05/2026$2,995.00
          27/09/202604/10/2026$2,995.00
          • An epic coast to coast journey through southern Italy riding from the Adriatic coast to the Tyrrhenian Sea
          • Exploring the UNESCO World Heritage sites of Alberobello, Matera, Padula and Paestum
          • Losing ourselves in the labyrinthic white washed alleyways of Noci and Tricarico
          • Climbing the hills of little-known Basilicata, to the hill-top villages of Castelmezzano, Calvello and Marsico Vetere
          • Cycling through the Dolomiti Lucane, southern Italy’s lesser-known Dolomites
          • Enjoying the roller-coaster ride along the Cilento Coast from Palinuro to Paestum
          • Sampling southern Italy’s best food and wine
          Photo Highlights Dates
          Guided
          Guided
          United Kingdom

          Land's End to John O'Groats Classic

          Guided Road Bike Tour

          Duration

          16 days

          Prices from

          $4,710 P.P.
          View Reviews
          20
          1
          2
          3
          4
          5
          Grade 3 - 4: Moderate/ Challenging
          More Info BOOK NOW

          Land's End to John O'Groats Classic

          Guided Road Bike Tour

          Start DateEnd DatePrice p.p.
          23/05/2026
          Fully Booked
          07/06/2026$4,710.00
          22/08/202606/09/2026$4,710.00
          • Ride the length of Britain from toe to tip and declare yourself an ‘End to Ender’
          • The camaraderie of completing the UK’s best challenge ride on a small group tour
          • 3 countries in 14 days of riding. 1,000 miles of Britain at its best
          • A unique LEJOG route along quiet roads through scenic countryside
          • Enjoy spectacular scenery from Cheddar Gorge to the Cairngorms
          • Experience the regional changes in tradition, culture and accents as you progress from county to county
          • Delicious picnics, country pubs and wonderful accommodation
          • Cornish pasties to haggis and everything in between
          Photo Highlights Dates
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          Not sure which trip's right for you? Just ask!

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

          Quote
          After over 40 tours with other operators, I was apprehensive about trying a new company, but have come away extremely pleased with Skedaddle!
          Bruce, Italy - Sardinian Mountains
          Quote
          All queries were replied almost immediately! Well done, Skedaddle, you have provided good consultant, good tour leader and good technical assistant.
          Sin Siew Tag, UK - Land's End to John O'Groats
          Quote
          This trip had something for everybody! The crew were fantastic, they were a vital part of the trip. The rest was the magic of Italy.
          Nigel, Italy - Grand Traverse
          Quote
          A fantastic journey of a lifetime led by excellent guides. Loved the Gorge du Verdon - tremendous climb and stupendous view.
          Miles, France - St Malo to Nice
          Quote
          I was the least experienced in the group - but was made to feel very comfortable and given lots of instruction and help.
          Catharine, France - Le Ventoux a Velo
          Quote
          Quite simply, there are not enough superlatives to describe how beautiful the Tuscan countryside and the accommodation chosen were!
          Robert, Italy - Tuscany Tourer
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