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          Extend your Summer of Cycling

          We found 19 Holidays in your search for:

          Destinations (74)
          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 (74)
          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 bike tour 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 fall, 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 fall bike tours. 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 Tours
          • POPULAR GROUP DEPARTURES

          Page 2 of 2

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          Guided
          Guided
          United Kingdom

          Eden Valley and the North Pennines

          Guided Road Bike Tour

          Duration

          6 days

          Prices from

          $1,565 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.
          26/07/2026
          Fully Booked
          31/07/2026$1,565.00
          20/09/202625/09/2026$1,565.00
          • 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
          Spain

          Roads of Ronda

          Guided Road Bike Tour

          Duration

          7 days

          Prices from

          $3,035 P.P.
          View Reviews
          8
          1
          2
          3
          4
          5
          Grade 3: Moderate
          More Info BOOK NOW

          Roads of Ronda

          Guided Road Bike Tour

          Start DateEnd DatePrice p.p.
          08/11/202614/11/2026$3,035.00
          • 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
          Spain

          Sierra Nevada and Granada

          Guided Road Bike Tour

          Duration

          7 days

          Prices from

          $2,835 P.P.
          View Reviews
          2
          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.
          18/10/2026
          Guaranteed
          24/10/2026$2,835.00
          03/05/202709/05/2027$2,850.00
          20/10/202726/10/2027$2,850.00
          • 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
          France

          Haute Dordogne

          Guided Road Bike Tour

          Duration

          8 days

          Prices from

          $3,565 P.P.
          View Reviews
          6
          1
          2
          3
          4
          5
          Grade 2 - 3: Gentle/Moderate
          More Info BOOK NOW

          Haute Dordogne

          Guided Road Bike Tour

          Start DateEnd DatePrice p.p.
          05/09/2026
          Last Spaces
          12/09/2026$3,565.00
          05/06/202712/06/2027$3,710.00
          28/08/202704/09/2027$3,710.00
          • 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
          Italy

          Coast to Coast - L'Adriatico al Tirreno

          Guided Road Bike Tour

          Duration

          9 days

          Prices from

          $3,850 P.P.
          View Reviews
          13
          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.
          12/09/2026
          Guaranteed
          20/09/2026$3,850.00
          22/05/202730/05/2027$4,035.00
          11/09/202719/09/2027$4,035.00
          • 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 Bike Tour

          Duration

          6 days

          Prices from

          $1,850 P.P.
          View Reviews
          2
          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.
          19/07/2026
          Fully Booked
          24/07/2026$1,850.00
          13/09/2026
          Last Spaces
          18/09/2026$1,850.00
          25/07/202730/07/2027$1,910.00
          19/09/202724/09/2027$1,910.00
          • 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 Bike Tour

          Duration

          7 days

          Prices from

          $3,280 P.P.
          View Reviews
          8
          1
          2
          3
          4
          5
          Grade 3: Moderate
          More Info BOOK NOW

          La Rioja - Ruta del Vino

          Guided Road Bike Tour

          Start DateEnd DatePrice p.p.
          27/09/2026
          Guaranteed
          03/10/2026$3,280.00
          14/06/202720/06/2027$3,350.00
          16/09/202722/09/2027$3,350.00
          • 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 Bike Tour

          Duration

          22 days

          Prices from

          $8,250 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 Bike Tour

          Start DateEnd DatePrice p.p.
          03/10/2026
          Last Spaces
          24/10/2026$8,250.00
          09/04/202730/04/2027$8,490.00
          05/10/202726/10/2027$8,490.00
          • 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 Bike Tour

          Duration

          8 days

          Prices from

          $3,850 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 Bike Tour

          Start DateEnd DatePrice p.p.
          17/10/2026
          Guaranteed
          24/10/2026$3,850.00
          • 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
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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 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
          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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