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            Road Cycling Journeys

            We found 18 Holidays in your search for:

            Destinations (83)
            Types of Cycling / Grades (1)
            Departure Month

            2025

            2026

            2027

            Level of Support

            We found 18 Holidays in your search for:

            Select Order Order By
            Destinations (83)
            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 Holidays
            • Place To Place Journeys

            Page 2 of 2

            Select Order Order By
            Guided
            Guided
            Spain

            Basque Country to Andalucia Classic - North to South

            Guided Road Cycling Holiday

            Duration

            16 days

            Prices from

            £4,135 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 Cycling Holiday

            Start DateEnd DatePrice p.p.
            10/04/202625/04/2026£4,135.00
            27/09/202612/10/2026£4,135.00
            • 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
            Italy

            Grand Traverse Explorer - South to North

            Guided Road Cycling Holiday

            Duration

            22 days

            Prices from

            £5,495 P.P.
            View Reviews
            5
            1
            2
            3
            4
            5
            Grade 3 - 4: Moderate/ Challenging
            More Info BOOK NOW

            Grand Traverse Explorer - South to North

            Guided Road Cycling Holiday

            Start DateEnd DatePrice p.p.
            25/04/202616/05/2026£5,495.00
            29/08/2026
            Guaranteed
            19/09/2026£5,495.00
            • Riding up the backbone of Italy on a stunning route which takes in some of the best road cycling that Italy has to offer
            • Cycling through 10 UNESCO World Heritage sites and 5 National Parks
            • Visiting some of the most important historical and artistic cities in Italy: Lecce, Assisi, Siena, Venice
            • The camaraderie of your fellow cyclists who’ll be joining you on this incredible tour
            • Immersing yourself in Italian culture – meeting the friendly locals, experiencing delicious culinary specialties and tasting the wines of each region
            • Cycling from the most south-easterly point of the heel of Italy up to Venice, having ridden nearly 1,100 miles and climbed almost 22,000 metres!
            Photo Highlights Dates
            Guided
            Guided
            Portugal

            Atlantic Escape

            Guided Road Cycling Holiday

            Duration

            10 days

            Prices from

            £2,895 P.P.
            View Reviews
            9
            1
            2
            3
            4
            5
            Grade 3 : Moderate
            More Info BOOK NOW

            Atlantic Escape

            Guided Road Cycling Holiday

            Start DateEnd DatePrice p.p.
            25/04/202604/05/2026£2,895.00
            31/10/202609/11/2026£2,895.00
            • Stunning Sintra and its sunsets
            • The lovely fishing village of Nazare
            • Incredible accommodation in 4 star hotels each night
            • Views from the Arrabida mountains
            • Coastal riding and beautiful beaches
            • Reaching mainland Europe’s most southwesterly point by bike!
            Photo Highlights Dates
            Guided
            Guided
            Italy

            Coast to Coast - L'Adriatico al Tirreno

            Guided Road Cycling Holiday

            Duration

            9 days

            Prices from

            £2,695 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 Cycling Holiday

            Start DateEnd DatePrice p.p.
            16/05/202624/05/2026£2,695.00
            12/09/2026
            Guaranteed
            20/09/2026£2,695.00
            • 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
            Guided
            Guided
            Spain

            Bilbao to Santiago

            Guided Road Cycling Holiday

            Duration

            11 days

            Prices from

            £3,225 P.P.
            View Reviews
            4
            1
            2
            3
            4
            5
            Grade 3 : Moderate
            More Info BOOK NOW

            Bilbao to Santiago

            Guided Road Cycling Holiday

            Start DateEnd DatePrice p.p.
            28/06/202608/07/2026£3,225.00
            07/09/2026
            Last Spaces
            17/09/2026£3,225.00
            • Riding along the stunning and dramatic Cantabrian coastline
            • 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
            • The arrival at ‘the end of the world’ and awesome Cape Finisterre
            Photo Highlights Dates
            Guided
            Guided
            Scotland

            Scotland - Kirkpatrick Coast to Coast

            Guided Road Cycling Holiday

            Duration

            6 days

            Prices from

            £1,325 P.P.
            View Reviews
            4
            1
            2
            3
            4
            5
            Grade 3 : Moderate
            More Info BOOK NOW

            Scotland - Kirkpatrick Coast to Coast

            Guided Road Cycling Holiday

            Start DateEnd DatePrice p.p.
            10/05/202615/05/2026£1,325.00
            19/07/202624/07/2026£1,325.00
            13/09/202618/09/2026£1,325.00
            • 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
            Self-Guided
            Self-Guided
            Italy

            Sardinia - Coast to Coast

            Self-Guided Road Cycling Holiday

            Duration

            8 days

            Prices from

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

            Sardinia - Coast to Coast

            Self-Guided Road Cycling Holiday

            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 from 08 Jun – 31 Aug)

            Season 1 – £1595 29 Mar – 07 Jun / 09 Sep – 26 Oct

            Season 2 – £1765 01 Sept – 08 Sept

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

            • Riding the roller-coaster road below Mount Arcuentu to the west coast
            • Exploring the UNESCO heritage site of Su Nuraxi at Barumini
            • Taking a dip in the emerald waters of Sardinia
            • Cycling through the Sardinian “Blue Zone”
            • Dining on delicious home cooked food, washed down with tasty local wine!
            • The stunning descent to Bari Sardo on the East Coast
            Photo Highlights Dates
            Guided
            Guided
            United Kingdom

            Land's End to John O'Groats Classic

            Guided Road Cycling Holiday

            Duration

            16 days

            Prices from

            £3,295 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 Cycling Holiday

            Start DateEnd DatePrice p.p.
            23/05/2026
            Fully Booked
            07/06/2026£3,295.00
            22/08/202606/09/2026£3,295.00
            • 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
            • Previous page
            • 1
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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
            Next

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