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            Small Group Road Cycling Tours

            We found 41 Holidays in your search for:

            Destinations (72)
            Types of Cycling / Grades (1)
            Departure Month

            2025

            2026

            2027

            Level of Support

            We found 41 Holidays in your search for:

            Select Order Order By
            Destinations (72)
            Types of Cycling / Grades (1)
            Departure Month

            2025

            2026

            2027

            Level of Support

            Join a peloton of like-minded riders on a small group tour with Skedaddle! Our group road cycling tours welcome everyone from solo travellers to groups of friends. You’ll love the fun and camaraderie as you ride along some of the world’s most beautiful roads.

            Our experienced guides and tour leaders are here to make sure every pedal stroke of your holiday runs like clockwork, plus you’ll have the back-up of a support vehicle to assist with mechanical issues and extra supplies. We’ll also arrange your luggage transfers and accommodation so all you need to worry about is focusing on tackling that next climb and taking in the gorgeous scenery as you ride. 

            • All Cycling Holidays
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            • SMALL GROUP CYCLING TOURS

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            Guided
            Guided
            Italy

            Alps and Dolomites - Giants of the Giro

            Guided Road Bike Tour

            Duration

            9 days

            Prices from

            $3,525 P.P.
            View Reviews
            17
            1
            2
            3
            4
            5
            Grade 4 - 5
            More Info BOOK NOW

            Alps and Dolomites - Giants of the Giro

            Guided Road Bike Tour

            Start DateEnd DatePrice p.p.
            * 25/07/2025
            Fully Booked
            02/08/2025$3,525.00
            * 16/08/2025
            Contact Us
            24/08/2025$3,525.00
            25/07/202602/08/2026$3,710.00
            22/08/202630/08/2026$3,710.00
            • Cycling through the best alpine and dolomite scenery of Italy
            • Climbing the iconic Mortirolo, Passo Gavia and Passo Stelvio of Giro d’Italia fame
            • Enjoying post-ride relaxation in typical chalet-style mountain hotels
            • Re-charging your energy levels every evening with tasty local fayre
            • Testing your legs and endurance on the final Monte Grappa climb
            • Enjoying an aperitif in the lively towns of San Pellegrino Terme, Bormio and Bassano del Grappa
            Photo Highlights Dates
            Guided
            Guided
            Italy

            Coast to Coast - L'Adriatico al Tirreno

            Guided Road Bike Tour

            Duration

            9 days

            Prices from

            $3,665 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.
            13/09/2025
            Guaranteed
            21/09/2025$3,665.00
            16/05/202624/05/2026$3,850.00
            12/09/202620/09/2026$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
            Guided
            Guided
            United Kingdom

            Scotland - Tour d'Ecosse

            Guided Road Bike Tour

            Duration

            8 days

            Prices from

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

            Scotland - Tour d'Ecosse

            Guided Road Bike Tour

            Start DateEnd DatePrice p.p.
            * 19/07/2025
            Fully Booked
            26/07/2025$2,525.00
            30/08/2025
            Last Spaces
            06/09/2025$2,525.00
            02/05/202609/05/2026$2,650.00
            23/05/202630/05/2026$2,650.00
            13/06/202620/06/2026$2,650.00
            04/07/202611/07/2026$2,650.00
            08/08/202615/08/2026$2,650.00
            05/09/202612/09/2026$2,650.00
            • Quiet single-track roads for miles on end
            • Bealach Na Ba – the greatest road ascent in the UK
            • Feasting on fresh seafood after a day in the saddle
            • Stunning views out over the Isle of Skye
            • Cycling the peaceful lochside roads
            • The swooping coastal road from Ullapool to Kinlochewe
            Photo Highlights Dates
            Guided
            Guided
            Norway

            Classic Fjords

            Guided Road Bike Tour

            Duration

            9 days

            Prices from

            $6,995 P.P.
            View Reviews
            3
            1
            2
            3
            4
            5
            Grade 3: Moderate
            More Info BOOK NOW

            Classic Fjords

            Guided Road Bike Tour

            Start DateEnd DatePrice p.p.
            13/06/202621/06/2026$6,995.00
            29/08/202606/09/2026$6,995.00
            • The natural beauty of the Norwegian landscape, fjords, mountains, waterfalls and coastlines
            • Narrow and dramatic Norangsdalen Valley & the beautiful coastal roads of Hjørundfjorden
            • Scenic, pollution-free, quiet roads and the freshest, cleanest air you can breathe
            • Cycling the shores of world-famous Sognefjord and beautiful Balestrand
            • Trollstigen Pass (The Troll’s Ladder) Norway’s most spectacular mountain road
            • Cruising along the UNESCO listed Geirangerfjord by ferry
            • Ålesund, Norway’s most beautiful city showcasing its impressive Art Nouveau architecture
            Photo Highlights Dates
            Guided
            Guided
            United Kingdom

            Eden Valley and the North Pennines

            Guided Road Bike Tour

            Duration

            6 days

            Prices from

            $1,525 P.P.
            View Reviews
            3
            1
            2
            3
            4
            5
            Grade 3 - 4: Moderate/ Challenging
            More Info BOOK NOW

            Eden Valley and the North Pennines

            Guided Road Bike Tour

            Start DateEnd DatePrice p.p.
            14/09/2025
            Guaranteed
            19/09/2025$1,525.00
            26/07/202631/07/2026$1,600.00
            20/09/202625/09/2026$1,600.00
            • Admiring the rugged natural beauty of the North Pennines
            • Riding up to the top of Hartside – a Tour of Britain favourite – from both directions
            • Miles and miles of quiet picturesque valleys and dramatic moorland
            • Pedalling up to Alston, the ‘joint highest market town’ in England
            • Cycling through the Howgill Fells, perfectly situated between the Lake District and Yorkshire Dales National Parks
            • Enjoying a well deserved pint of Pennine Pale Ale at the end of a day in the saddle
            Photo Highlights Dates
            Guided
            Guided
            United Kingdom

            Scotland - Kirkpatrick Coast to Coast

            Guided Road Bike Tour

            Duration

            6 days

            Prices from

            $1,795 P.P.
            View Reviews
            6
            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.
            * 24/08/2025
            Guaranteed
            29/08/2025$1,795.00
            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

            NEW! Coast to Coast - Puglia to Cilento

            Guided Road Bike Tour

            Duration

            8 days

            Prices from

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

            NEW! Coast to Coast - Puglia to Cilento

            Guided Road Bike Tour

            Start DateEnd DatePrice p.p.
            28/09/2025
            Guaranteed
            05/10/2025$2,850.00
            06/10/2025
            Guaranteed
            13/10/2025$2,850.00
            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
            Japan

            NEW! Shimanami Kaido, Shikoku & Kyoto

            Guided Road Bike Tour

            Duration

            15 days

            Prices from

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

            NEW! Shimanami Kaido, Shikoku & Kyoto

            Guided Road Bike Tour

            Start DateEnd DatePrice p.p.
            22/10/2025
            Fully Booked
            05/11/2025$10,850.00
            09/05/202623/05/2026$11,135.00
            • Riding across the famous Shimanami Kaido cycling bridges
            • Traversing Shikoku’s quiet mountain roads and rolling coastline
            • Experiencing traditional Japanese cuisine, accommodations, and hospitality
            • Reaching Cape Ashizuri, the southernmost tip of Shikoku Island
            • Descending to the banks of the Shimanto River, one of Japan’s last unspoilt waterways
            • Passing through the magnificent Oboke and Koboke Gorges
            • Exploring Kyoto, Japan’s beautiful and historic cultural capital
            Photo Highlights Dates
            Guided
            Guided
            Czech Republic, Austria, Slovenia & Italy

            NEW! Prague to Venice

            Guided Road Bike Tour

            Duration

            21 days

            Prices from

            $8,250 P.P.
            1
            2
            3
            4
            5
            Grade 3: Moderate
            More Info BOOK NOW

            NEW! Prague to Venice

            Guided Road Bike Tour

            Start DateEnd DatePrice p.p.
            06/06/2026
            Fully Booked
            26/06/2026$8,250.00
            04/07/2026
            Fully Booked
            24/07/2026$8,250.00
            01/08/2026
            Fully Booked
            21/08/2026$8,250.00
            05/06/202725/06/2027$8,850.00
            03/07/202723/07/2027$8,850.00
            • A journey from Central Europe to the Mediterranean through four European countries
            • Visit the vibrant capitals of Prague, Vienna and Ljubljana
            • Learn about the historical Central European regions of Bohemia and Styria
            • Explore the UNESCO World Heritage sites of Prague, Cesky Krumlov, Vienna, Graz, and Venice
            • Have a well deserved end-of-ride pilsner seated in the village square of a little Bohemian village
            • Enjoy quiet countryside roads with sweeping views all the way from Prague to Vienna
            • Staying in quality accommodation, with warm traditional hospitality
            • Feast on the traditional dishes, desserts and drinks of the Czech, Austrian and Slovenian cuisine.
            Photo Highlights Dates
            Guided
            Guided
            France

            Corsica - The Beautiful Isle

            Guided Road Bike Tour

            Duration

            8 days

            Prices from

            $3,280 P.P.
            View Reviews
            13
            1
            2
            3
            4
            5
            Grade 3: Moderate
            More Info BOOK NOW

            Corsica - The Beautiful Isle

            Guided Road Bike Tour

            Start DateEnd DatePrice p.p.
            13/09/2025
            Fully Booked
            20/09/2025$3,280.00
            16/05/202623/05/2026$3,425.00
            12/09/202619/09/2026$3,425.00
            • One of the most dramatic coastal rides in Europe
            • The descent through the Scala di Santa Regina between the Col de Vergio and Corte
            • Chestnut beers all round in Corte, the ancient and rustic mountain capital
            • Mouthwatering local cuisine, charcuterie and cheeses
            • The Castagniccia – Corsica’s most unspoiled region of chestnut forest, wild boar and traditional rural villages
            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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