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            Extend your Summer of Cycling

            We found 19 Holidays in your search for:

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

            2026

            2027

            2028

            Level of Support

            We found 19 Holidays in your search for:

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

            2026

            2027

            2028

            Level of Support

            Not ready to put your bike away just yet? Extend your summer of cycling with a late-season escape. If you're looking for a cycling holiday in late August, September or October, you're in the right place. 

            As the peak holiday season comes to an end, it's the perfect time to enjoy quieter roads and trails, fewer crowds and more comfortable temperatures. Across much of Southern Europe, warm sunshine lingers well into autumn, whilst September in the UK is one of the very best times to ride, plus our most popular month for departures. 

            Whether you're looking for one last escape before winter or simply want to make the most of the cycling season, explore our late summer and autumn cycling holidays. Many departures are filling up fast, so don't miss your chance to enjoy one more unforgettable cycling adventure this year! 

            • All Cycling Holidays
            • All Road Cycling Holidays
            • POPULAR GROUP DEPARTURES

            Page 2 of 2

            Select Order Order By
            Guided
            Guided
            Spain

            Roads of Ronda

            Guided Road Cycling Holiday

            Duration

            7 days

            Prices from

            £2,125 P.P.
            View Reviews
            9
            1
            2
            3
            4
            5
            Grade 3 : Moderate
            More Info BOOK NOW

            Roads of Ronda

            Guided Road Cycling Holiday

            Start DateEnd DatePrice p.p.
            08/11/202614/11/2026£2,125.00
            • Staying in the quintessentially Spanish town of Old Ronda
            • Cycling through the rugged, ‘bandit country’ of the Sierra de las Nieves
            • Climbing the 1,200m up ‘The Colossus’
            • The seemingly never-ending descent down to the fine sands of Estepona
            • Taking a refreshing post ride dip in the Med
            • Tasty tapas and sunset sangrias
            Photo Highlights Dates
            Guided
            Guided
            France

            Haute Dordogne

            Guided Road Cycling Holiday

            Duration

            8 days

            Prices from

            £2,495 P.P.
            View Reviews
            6
            1
            2
            3
            4
            5
            Grade 2 - 3: Gentle to Moderate
            More Info BOOK NOW

            Haute Dordogne

            Guided Road Cycling Holiday

            Start DateEnd DatePrice p.p.
            05/09/2026
            Last Spaces
            12/09/2026£2,495.00
            05/06/202712/06/2027£2,595.00
            28/08/202704/09/2027£2,595.00
            • Sampling a glass of red in Cahors – home of Malbec
            • Winding our way along the dramatic Vallée du Célé
            • Cycling along to the sound of cowbells near Velzic
            • Conquering the Pas de Peyrol and drinking in the views
            • Rocamadour and the descent from its lofty heights
            • Marvelling at the Massif Centrale as we cycle through its distinctive landscapes
            Photo Highlights Dates
            Guided
            Guided
            France

            St Malo to Nice Explorer

            Guided Road Cycling Holiday

            Duration

            20 days

            Prices from

            £5,895 P.P.
            View Reviews
            19
            1
            2
            3
            4
            5
            Grade 3 : Moderate
            More Info BOOK NOW

            St Malo to Nice Explorer

            Guided Road Cycling Holiday

            Start DateEnd DatePrice p.p.
            07/09/2026
            Guaranteed
            26/09/2026£5,895.00
            25/05/202713/06/2027£6,075.00
            06/09/202725/09/2027£6,075.00
            • 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

            Alps and Dolomites - Giants of the Giro

            Guided Road Cycling Holiday

            Duration

            9 days

            Prices from

            £2,495 P.P.
            View Reviews
            17
            1
            2
            3
            4
            5
            Grade 4 - 5: Challenging/ Demanding
            More Info BOOK NOW

            Alps and Dolomites - Giants of the Giro

            Guided Road Cycling Holiday

            Start DateEnd DatePrice p.p.
            25/07/2026
            Guaranteed
            02/08/2026£2,495.00
            22/08/2026
            Guaranteed
            30/08/2026£2,495.00
            17/07/202725/07/2027£2,595.00
            21/08/202729/08/2027£2,595.00
            • 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 Cycling Holiday

            Duration

            9 days

            Prices from

            £2,695 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.
            12/09/2026
            Guaranteed
            20/09/2026£2,695.00
            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
            Scotland

            Scotland - Kirkpatrick Coast to Coast

            Guided Road Cycling Holiday

            Duration

            6 days

            Prices from

            £1,295 P.P.
            View Reviews
            2
            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.
            19/07/2026
            Fully Booked
            24/07/2026£1,295.00
            13/09/2026
            Last Spaces
            18/09/2026£1,295.00
            25/07/202730/07/2027£1,335.00
            19/09/202724/09/2027£1,335.00
            • 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
            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
            Guaranteed
            03/10/2026£2,295.00
            14/06/202720/06/2027£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
            Spain & Portugal

            NEW! Trans Iberia - Barcelona to Porto

            Guided Road Cycling Holiday

            Duration

            22 days

            Prices from

            £5,775 P.P.
            View Reviews
            3
            1
            2
            3
            4
            5
            Grade 3 : Moderate
            More Info BOOK NOW

            NEW! Trans Iberia - Barcelona to Porto

            Guided Road Cycling Holiday

            Start DateEnd DatePrice p.p.
            03/10/2026
            Last Spaces
            24/10/2026£5,775.00
            09/04/202730/04/2027£5,945.00
            05/10/202726/10/2027£5,945.00
            • Starting the journey in the cultural capital of Barcelona
            • Crossing the stunning mountain roads of the Sierra de Gredos
            • Delighting in the varied regional specialities of the Iberian Peninsula
            • Discovering the fortified city of Toledo
            • Exploring the ancient narrow streets of Morella, Albarracín and Chinchón
            • Toasting the end of the ride with a glass of Port on the banks of the Douro
            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
            Guaranteed
            24/10/2026£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
            • 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
            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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