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            Small Group Road Cycling Holidays

            We found 38 Holidays in your search for:

            Destinations (82)
            Types of Cycling / Grades (1)
            Departure Month

            2026

            2027

            2028

            Level of Support

            We found 38 Holidays in your search for:

            Select Order Order By
            Destinations (82)
            Types of Cycling / Grades (1)
            Departure Month

            2026

            2027

            2028

            Level of Support

            Join a peloton of like-minded riders on a small group holiday 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
            • All Road Cycling Holidays
            • SMALL GROUP CYCLING HOLIDAYS

            Page 3 of 4

            Select Order Order By
            Guided
            Guided
            Italy

            Grand Traverse Classic - North to South

            Guided Road Cycling Holiday

            Duration

            17 days

            Prices from

            £4,195 P.P.
            View Reviews
            9
            1
            2
            3
            4
            5
            Grade 4 : Challenging
            More Info BOOK NOW

            Grand Traverse Classic - North to South

            Guided Road Cycling Holiday

            Start DateEnd DatePrice p.p.
            24/09/2026
            Last Spaces
            10/10/2026£4,195.00
            20/05/202705/06/2027£4,325.00
            23/09/202709/10/2027£4,325.00
            • Riding down 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: Lucca, San Gimignano, Pienza, Assisi and Lecce
            • 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 to the most southerly point of Italy, having ridden nearly 1,100 miles and climbed over 21,000 metres!
            Photo Highlights Dates
            Guided
            Guided
            Spain

            Pyrenean Traverse

            Guided Road Cycling Holiday

            Duration

            12 days

            Prices from

            £3,595 P.P.
            View Reviews
            3
            1
            2
            3
            4
            5
            Grade 4 : Challenging
            More Info BOOK NOW

            Pyrenean Traverse

            Guided Road Cycling Holiday

            Start DateEnd DatePrice p.p.
            04/07/202715/07/2027£3,595.00
            • A first evening feasting on a traditional Basque supper in beautiful Honarribia
            • Conquering classic climbs of the Pyrenees including the Cat 1 Puerto de Portalet
            • Winding through remote villages on unbelievably quiet mountain roads
            • Gazing in awe at the highest mountains in the Pyrenees in the Parque de Aneto
            • Wondering through the medieval streets of beautiful Ainsa
            • Finishing the week with a glass of Cava on the beach in picturesque Cadaqués
            Photo Highlights Dates
            Guided
            Guided
            Portugal

            Vineyards of the Douro Valley

            Guided Road Cycling Holiday

            Duration

            8 days

            Prices from

            £2,695 P.P.
            View Reviews
            2
            1
            2
            3
            4
            5
            Grade 3 - 4: Moderate/ Challenging
            More Info BOOK NOW

            Vineyards of the Douro Valley

            Guided Road Cycling Holiday

            Start DateEnd DatePrice p.p.
            17/10/2026
            Last Spaces
            24/10/2026£2,695.00
            17/04/202724/04/2027£2,695.00
            09/10/202716/10/2027£2,695.00
            • Riding along the Douro river through immense vineyards surrounded by terraced slopes
            • Staying in carefully selected accommodations, with opportunities to visit Port wine cellars and taste local wines along the way.
            • Riding on the N222 in the heart of the Alto Douro, considered one of the most beautiful roads in the world, with its jaw dropping scenery
            • The historic fortified village of Almeida
            • Tackling the dramatic climb to the summit of Torre in the Serra da Estrela, the highest point of mainland Portugal
            • The final hotel at Unhais da Serra, an unexpected oasis at the end of the trip
            Photo Highlights Dates
            Guided
            Guided
            Portugal

            Atlantic Escape

            Guided Road Cycling Holiday

            Duration

            10 days

            Prices from

            £2,895 P.P.
            View Reviews
            10
            1
            2
            3
            4
            5
            Grade 3 : Moderate
            More Info BOOK NOW

            Atlantic Escape

            Guided Road Cycling Holiday

            Start DateEnd DatePrice p.p.
            31/10/202609/11/2026£2,895.00
            01/05/202710/05/2027£2,895.00
            23/10/202701/11/2027£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
            Spain

            Andalucia - Los Pueblos Blancos

            Guided Road Cycling Holiday

            Duration

            8 days

            Prices from

            £2,195 P.P.
            View Reviews
            5
            1
            2
            3
            4
            5
            Grade 2 - 3: Gentle to Moderate
            More Info BOOK NOW

            Andalucia - Los Pueblos Blancos

            Guided Road Cycling Holiday

            Start DateEnd DatePrice p.p.
            25/10/2026
            Contact Us
            01/11/2026£2,195.00
            28/12/202604/01/2027£2,495.00
            • Riding the beautiful Serrania de Ronda, past white villages, chestnut groves and craggy sierras
            • A fantastic mixture of great small rural hotels
            • Exploring beautiful Ronda, perched on its magnificent gorge
            • Reaching the dramatic Puerto de las Palomas
            • Grazalema, nestled below atmospheric, limestone mountains
            • Sipping local sherries with tasty tapas in the local bodegas
            Photo Highlights Dates
            Guided
            Guided
            Italy

            Grand Traverse Explorer - South to North

            Guided Road Cycling Holiday

            Duration

            22 days

            Prices from

            £5,655 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.
            24/04/202715/05/2027£5,655.00
            28/08/202718/09/2027£5,655.00
            • 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
            Spain

            La Rioja - Ruta del Vino

            Guided Road Cycling Holiday

            Duration

            7 days

            Prices from

            £2,295 P.P.
            View Reviews
            8
            1
            2
            3
            4
            5
            Grade 3 : Moderate
            More Info BOOK NOW

            La Rioja - Ruta del Vino

            Guided Road Cycling Holiday

            Start DateEnd DatePrice p.p.
            27/09/2026
            Fully Booked
            03/10/2026£2,295.00
            07/06/202713/06/2027£2,345.00
            16/09/202722/09/2027£2,345.00
            • Staying at the fantastic San Millan de la Cogolla monastery, a World Heritage Site.
            • Cycling high along the limestone cliffs of the Sierra de Cantabria
            • Enjoying the atmospheric, medieval towns of Ezacary and Laguardia
            • Wine tasting in a Riojan bodega (or two!)
            • Cycling through Mediterranean forests, along mountainsides and through endless vineyards
            • Rolling along the Rio Ebro into Logroño for an authentic slice of tapas heaven in Calle Laurel
            Photo Highlights Dates
            Guided
            Guided
            Italy

            Coast to Coast - L'Adriatico al Tirreno

            Guided Road Cycling Holiday

            Duration

            9 days

            Prices from

            £2,825 P.P.
            View Reviews
            12
            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.
            22/05/202730/05/2027£2,825.00
            11/09/202719/09/2027£2,825.00
            • 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

            Basque Country to Andalucia Explorer - North to South

            Guided Road Cycling Holiday

            Duration

            21 days

            Prices from

            £5,355 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 Cycling Holiday

            Start DateEnd DatePrice p.p.
            08/05/202728/05/2027£5,355.00
            28/08/202717/09/2027£5,355.00
            • 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
            Spain

            Bilbao to Santiago

            Guided Road Cycling Holiday

            Duration

            11 days

            Prices from

            £3,295 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.
            26/06/202706/07/2027£3,295.00
            05/09/202715/09/2027£3,295.00
            • 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
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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
            100% perfection from Saddle Skedaddle on a recent road tour. Amazing route, exceptional accommodation, brilliant guides, quality hire bikes.....11 out of 10!
            Andy - Puglia to Cilento
            Quote
            All queries were replied almost immediately! Well done, Skedaddle, you have provided good consultant, good tour leader and good technical assistant.
            Sin Siew - 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
            The trip was amazing and exceeded my expectations. The route was spectacular and well thought, a perfect mix of challenges and easier days to cater for different abilities, levels of fitness and recovery times, without ever being boring.
            Lisa - Colombia Emerald Mountains
            Next

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            If you’re looking for long distance cycle routes in the UK, you’ll likely have encountered the little blue and red signs marking the incredible National Cycle Network. For more than 30 years, Walk Wheel Cycle Trust has been the custodian of this network, developing and maintaining routes that make exploring the UK by bike more ...

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            September 11, 2026
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            Dan Hirst, Head of Skedaddle Espana
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            Cycling in the Pyrenees

            Cycling in the Pyrenees: A Tale of Two Journeys – France versus Spain

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