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          Extend your Summer of Cycling

          We found 30 Holidays in your search for:

          Destinations (74)
          Types of Cycling / Grades (7)
          Departure Month

          2026

          2027

          2028

          Level of Support

          We found 30 Holidays in your search for:

          Select Order Order By
          Destinations (74)
          Types of Cycling / Grades (7)
          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
          • POPULAR GROUP DEPARTURES

          Page 3 of 3

          Select Order Order By
          Guided
          Guided
          Spain

          Roads of Ronda

          Guided Road Bike Tour

          Duration

          7 days

          Prices from

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

          Roads of Ronda

          Guided Road Bike Tour

          Start DateEnd DatePrice p.p.
          08/11/2026
          Guaranteed
          14/11/2026$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
          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
          Last Spaces
          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
          Italy

          Tuscany to Rome

          Guided Electric Bike Tour

          Duration

          8 days

          Prices from

          $3,425 P.P.
          View Reviews
          7
          1
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          3
          4
          5
          Grade 3 : Moderate
          More Info BOOK NOW

          Tuscany to Rome

          Guided Electric Bike Tour

          E-BIKE TOUR

          This holiday has been designed as an e-bike tour allowing you to experience more on two wheels whilst riding with like-minded Skedaddlers. Confident cyclists will enjoy the boost from a battery for those cheeky climbs and longer distances. With less effort required on the bike, you’ll have more energy at the end of the day for off-the-bike activities. Remember to select your e-bike hire when you book your holiday with us.

          Start DateEnd DatePrice p.p.
          12/09/2026
          Last Spaces
          19/09/2026$3,425.00
          08/05/202715/05/2027$3,565.00
          04/09/202711/09/2027$3,565.00
          • Staying in Tuscan accommodation overlooking stunning landscapes
          • Discovering the amazing towns of Siena, San Quirico and Pienza
          • Sampling the best wines of Chianti, Montepulciano and Montalcino
          • Enjoying the journey from Tuscany to Rome on a variety of terrain, including ancient Roman roads
          • Exploring the lesser-known historical towns of Lazio, such as Sutri with it’s Roman amphitheatre
          • The sense of achievement riding into St Peter’s Square in Rome
          Photo Highlights Dates
          Guided
          Guided
          Peru

          Sacred Valley of the Incas

          Guided Bike Tour

          Duration

          12 days

          Prices from

          $4,080 P.P.
          View Reviews
          2
          1
          2
          3
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          5
          Grade 2 - 3: Moderate/ Active
          More Info BOOK NOW

          Sacred Valley of the Incas

          Guided Bike Tour

          Start DateEnd DatePrice p.p.
          19/09/2026
          Guaranteed
          30/09/2026$4,080.00
          05/06/202716/06/2027$4,335.00
          14/08/202725/08/2027$4,335.00
          18/09/202729/09/2027$4,335.00
          • Amazing biking and a day of hiking the Inca Trail
          • The imposing Inca ruins of the Sacred Valley
          • Shopping for bargains at Pisac’s artisan market
          • Machu Picchu – One of the Wonders of the World
          • The world’s best Pisco sours and ceviche!
          • Colourful Cusco and the unspoiled Lares Valley
          Photo Highlights Dates
          Guided
          Guided
          Italy

          Tuscany - Strade Bianche Explorer

          Guided Gravel Riding Tour

          Duration

          8 days

          Prices from

          $3,180 P.P.
          View Reviews
          1
          1
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          3
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          5
          Grade 3-4 : Moderate/Chellenging
          More Info BOOK NOW

          Tuscany - Strade Bianche Explorer

          Guided Gravel Riding Tour

          Start DateEnd DatePrice p.p.
          20/09/2026
          Last Spaces
          27/09/2026$3,180.00
          24/04/202701/05/2027$3,280.00
          08/05/202715/05/2027$3,280.00
          25/09/202702/10/2027$3,280.00
          • Riding some of the classic Tuscany gravel routes including the Strade Bianche
          • Cycling through the historic wine regions of Tuscany, stopping off for a bit of wine tasting
          • Exploring the region on a mix of terrains
          • Riding the stunning UNESCO heritage region of Val d’Orcia
          • Relaxing in small villages for a coffee with the locals
          • Easing along the rolling hills of the ‘Colli Sienesi’
          • Chilling out with a post-ride Chianti or Brunello
          Photo Highlights Dates
          Guided
          Guided
          Spain & Portugal

          Trans Iberia - Barcelona to Porto

          Guided Road Bike Tour

          Duration

          22 days

          Prices from

          $8,250 P.P.
          View Reviews
          3
          1
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          3
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          5
          Grade 3 - 4: Moderate/ Challenging
          More Info BOOK NOW

          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
          • Cycling through 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
          Italy

          Sardinia - Island Flavours

          Guided Leisure Bike Tour

          Duration

          8 days

          Prices from

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

          Sardinia - Island Flavours

          Guided Leisure Bike Tour

          E-BIKE HIRE AVAILABLE

          This tour is well-suited to both regular bikes and pedal assist e-bikes, and you can choose to hire either when you book your tour with us. Confident cyclists will enjoy the boost from a battery for those cheeky climbs, and with less effort required on the bike, you’ll have more energy at the end of the day for off-the-bike activities. You may choose to hire an e-bike on a group or supported tour but bear in mind that the pace will be set to riders without an e-bike.

          Start DateEnd DatePrice p.p.
          12/09/2026
          Fully Booked
          19/09/2026$2,850.00
          10/10/2026
          Fully Booked
          17/10/2026$2,850.00
          17/04/202724/04/2027$2,995.00
          01/05/202708/05/2027$2,995.00
          11/09/202718/09/2027$2,995.00
          09/10/202716/10/2027$2,995.00
          • Checking out the UNESCO heritage site of Barumini Nuraghe
          • Enjoying the long descent to Fluminimaggiore and Masua
          • Sampling local specialties at Carloforte, on St Pietro island
          • Riding along the Nebida coastline and marvelling at the view of Pan di Zucchero
          • Experiencing the friendliness and hospitality of the Sardinian people
          • Discovering the white beaches along the south-west coastal road
          Photo Highlights Dates
          Guided
          Guided
          Spain

          Sensational Sierra Nevada

          Guided Mountain Bike Tour

          Duration

          7 days

          Prices from

          $2,850 P.P.
          View Reviews
          18
          1
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          3
          4
          5
          Grade 4 : Challenging
          More Info BOOK NOW

          Sensational Sierra Nevada

          Guided Mountain Bike Tour

          OPTIONAL E-MTB DEPARTURES

          We offer this holiday with an e-MTB only departure as well as regular trips where you can choose a normal bike or a pedal assist e-MTB hire. Boost your riding off the beaten track! Our e-MTB only departures offer experienced riders the chance to enjoy a phenomenal e-mountain biking adventure with Skedaddle. Hire one of our quality e-mountain bikes and experience the buzz of a pedal-assisted ride. You may choose to hire an e-MTB on a regular tour date for this holiday but bear in mind that the pace will be set to riders without an e-bike.

          Start DateEnd DatePrice p.p.
          11/10/2026
          Guaranteed
          17/10/2026$2,850.00
          08/11/2026 E-Bike Departure14/11/2026$2,850.00
          11/04/202717/04/2027$2,895.00
          23/10/2027 E-Bike Departure29/10/2027$2,895.00
          • Remote technical riding on seldom visited paths
          • Impressive views of the Sierra Nevada’s highest peaks
          • Testing climbs and descents on natural terrain
          • Re-fuelling on tasty local cuisine
          • Endless free-flowing trails through a bikers paradise
          • The beautiful white villages of Moorish origen in the dramatic Poquiera Valley
          Photo Highlights Dates
          Guided
          Guided
          Spain

          Andalucia - Costa de la Luz and Ancient Cadiz

          Guided Leisure Bike Tour

          Duration

          8 days

          Prices from

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

          Andalucia - Costa de la Luz and Ancient Cadiz

          Guided Leisure Bike Tour

          E-BIKE HIRE AVAILABLE

          This tour is well-suited to both regular bikes and pedal assist e-bikes, and you can choose to hire either when you book your tour with us. Confident cyclists will enjoy the boost from a battery for those cheeky climbs, and with less effort required on the bike, you’ll have more energy at the end of the day for off-the-bike activities. You may choose to hire an e-bike on a group or supported tour but bear in mind that the pace will be set to riders without an e-bike.

          Start DateEnd DatePrice p.p.
          17/10/2026
          Fully Booked
          24/10/2026$3,280.00
          20/10/2026
          Guaranteed
          27/10/2026$3,280.00
          30/03/202706/04/2027$3,325.00
          06/06/202713/06/2027$3,325.00
          19/09/202726/09/2027$3,325.00
          • Exploring the endless coastal trails surrounding Tarifa
          • Indulging in delicious, freshly-caught seafood in Sanlucar
          • Savouring a glass of sherry in a historic bodega within the Sherry Triangle
          • Immersing ourselves in true Andalucian culture and enjoying some Flamenco
          • Riding along the peaceful, traffic-free EuroVelo routes
          • Experiencing the lively, vibrant town of Tarifa, the gateway to two continents
          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
          Last Spaces
          24/10/2026$3,850.00
          17/04/202724/04/2027$3,850.00
          09/10/202716/10/2027$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
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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
          Saddle Skedaddle staff were excellent. Consistently high standards delivered year on year. Don't think I'd trust anybody else when booking a cycling holiday!
          Susan, Slovenia - Capital to Coast, Leisure Cycling Holiday
          Quote
          This was the best of the several organised bike tours I've been on by light years, and I'm now looking at doing other tours with Skedaddle.
          Jay, France - St Malo to Nice, Road Cycling Holiday
          Quote
          Everything about the Skedaddle operation was spot-on, great attention to detail both before and during the trip. I was impressed by all things on the trip, quality of food, route briefings, accommodation, maps. I could go on!
          Paul, Land's End to John O'Groats Classic - 16 Days
          Quote
          What one pays for is not having to worry about anything – and Skedaddle does an excellent job taking care of us. We haven’t tried the other tour companies but why bother when Skedaddle is top notch.
          Roger, France - Chateaux of the Loire
          Quote
          From the first day to the last, everything was fantastic. We never had to worry about anything. Hotels, van pick-ups, guides - you had it all covered!
          Carol and Jim - Peru, Cycling Holiday
          Quote
          On 10+ trips with Skedaddle they have always delivered great trips and service. You get what you pay for and Skedaddle are very good at providing well run cycling holidays.
          Rob, Italy - Sardinia Island Flavours
          Next

          News, Reviews & Stories

          5 best end to end cycle routes 

          There is something undeniably special about cycling the full length of a country. More than just a cycling holiday, these epic journeys allow you to experience a destination in a way few travellers ever do, watching landscapes and cultures change day by day from the saddle. For Skedaddle Travel Consultant Kerry Ashberry, our Iconic Journeys ...

          Kerry Ashberry
          August 21, 2026
          Cyclists riding over medieval bridge of medieval bridge in France from St Malo to Nice

          St Malo to Nice: The must-do electric bike tour in France

          Since it was first created by Skedaddle guides Hannah Reynolds and John Walsh over 15 years ago, our St Malo to Nice adventure has gone on to become one of our most popular Iconic Journeys.  For years, this epic French odyssey has wowed road cyclists on our ever popular 15-and 20-day tours. Now, for 2027, we’re excited to make this ...

          Hannah Reynolds
          August 20, 2026
          View of the Col d'Allos mountain pass in the French Alps

          Customer Story: Cycling Mont Ventoux and Alpe d’Huez

          After a long hiatus, Paul rejoined us on a Skedaddle tour in the French Alps to conquer classic climbs, including cycling Mont Ventoux. Discover his highlights of this epic road cycling trip below. If there was a prize for the longest gap between Saddle Skedaddle holidays, I might just walk away with it. In the ...

          paul streets
          Paul Streets
          August 3, 2026

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