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            Extend your Summer of Cycling

            We found 5 Holidays in your search for:

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

            2026

            2027

            2028

            Level of Support

            We found 5 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 Leisure Cycling Holidays
            • POPULAR GROUP DEPARTURES
            Select Order Order By
            Guided
            Guided
            United Kingdom

            Norfolk - Rebellion Way

            Guided Leisure Cycling Holiday

            Duration

            7 days

            Prices from

            £1,695 P.P.
            View Reviews
            9
            1
            2
            3
            4
            5
            Grade 3 : Moderate
            More Info BOOK NOW

            Norfolk - Rebellion Way

            Guided Leisure Cycling Holiday

            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.
            06/09/2026
            Guaranteed
            12/09/2026£1,695.00
            • Coastal cycling, beach houses and British seaside sights
            • Majestic manor houses and villages full of character and charm
            • Varied terrain from rolling country lanes to wooded ways
            • Tales of Boudicca and rebellions
            • Delightful Diss and stunning Holkham Hall
            • Miles of gentle pedalling through the Norfolk Broads
            • Posing with Captain Mainwaring in Thetford
            Photo Highlights Dates
            Guided
            Guided
            Italy

            Puglia

            Guided Leisure Cycling Holiday

            Duration

            8 days

            Prices from

            £2,295 P.P.
            View Reviews
            12
            1
            2
            3
            4
            5
            Grade 2: Gentle
            More Info BOOK NOW

            Puglia

            Guided Leisure Cycling Holiday

            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.
            20/09/2026
            Guaranteed
            27/09/2026£2,295.00
            10/04/202717/04/2027£2,395.00
            18/09/202725/09/2027£2,395.00
            • Cycling through wonderful landscapes of ancient olive groves, vineyards and stunning coastlines
            • Exploring the UNESCO World Heritage town of Alberobello and the Baroque city of Lecce
            • Discovering the traditional Trulli houses of Puglia
            • Relaxing each night in comfortable 3 and 4* hotels in authentic Apulian towns and villages
            • Stopping at beautiful sandy beaches with turquoise seas
            • Tasting delicious Apulian produce, like orecchiette and extra virgin olive oil
            Photo Highlights Dates
            Guided
            Guided
            Italy

            Tuscany to Rome

            Guided Electric Bike Holiday

            Duration

            8 days

            Prices from

            £2,395 P.P.
            View Reviews
            7
            1
            2
            3
            4
            5
            Grade 3 : Moderate
            More Info BOOK NOW

            Tuscany to Rome

            Guided Electric Bike Holiday

            E-BIKE HOLIDAY

            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£2,395.00
            08/05/202715/05/2027£2,495.00
            04/09/202711/09/2027£2,495.00
            • 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
            Scotland

            Scotland - The Caledonia Way

            Guided Leisure Cycling Holiday

            Duration

            8 days

            Prices from

            £2,095 P.P.
            View Reviews
            4
            1
            2
            3
            4
            5
            Grade 4: Active
            More Info BOOK NOW

            Scotland - The Caledonia Way

            Guided Leisure Cycling Holiday

            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.
            06/09/2026
            Last Spaces
            13/09/2026£2,095.00
            02/05/202709/05/2027£2,185.00
            23/05/202730/05/2027£2,185.00
            11/07/202718/07/2027£2,185.00
            05/09/202712/09/2027£2,185.00
            • Marvelling at the beauty of Kilmartin Glen and its ancient monuments
            • Enjoying traffic-free Caledonia Way cycleways and lovely canal side routes
            • Checking out Ben Nevis and The Grampians from Loch Linhe
            • Fort Augustus and taking on the legendary ascent of Glendoe
            • Exploring Knapdale – One of Scotland’s National Scenic Areas
            • Cycling to Scotland’s best-loved towns including Fort William and Fort Augustus
            Photo Highlights Dates
            Guided
            Guided
            Spain

            Andalucia - Costa de la Luz and Ancient Cadiz

            Guided Leisure Cycling Holiday

            Duration

            8 days

            Prices from

            £2,295 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 Cycling Holiday

            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£2,295.00
            20/10/2026
            Guaranteed
            27/10/2026£2,295.00
            30/03/202706/04/2027£2,325.00
            06/06/202713/06/2027£2,325.00
            19/09/202726/09/2027£2,325.00
            • 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

            Not sure which trip's right for you? Just ask!

            Get in touch and we'll help you find your perfect trip.

            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
            The guides and other group members really made the holiday enjoyable. Our guide was friendly, professional and knowledgeable.
            Elaine, Italy - Tuscany to Rome
            Quote
            All the services we received were first class. This was a real holiday and going with Skedaddle took all the stress of booking accommodation from home, route planning and so on, so all we had to do was enjoy the cycling. This has been one of the best holidays in my life.
            Alison, Italy - Sardinia Island Flavours
            Quote
            What do you like most about Skedaddle? Where do I start? The booking process, the hotels, the guides, the lunches, the places they go, the people I meet, the pit stops, the Skedaddle community, reliability, I can put my trust in them to provide a great and memorable experience.
            David, Austria & Italy - La Via Claudia
            Quote
            Skedaddle holidays are always great; you can ride your bike and they pretty much do the rest! Being able to use two wheels as a mode of transport to travel across the country, supported by Skedaddle, just shows the beauty, and power, of bikes. Thank you for making it possible!
            Kate, UK - C2C
            Quote
            We just LOVED the whole thing – route, weather, food, scenery, being outside – it was probably one of the best holidays we have had.
            Inese, Austria - The Danube Cyclepath
            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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