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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 1 of 2

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            Guided
            Guided
            Spain

            Basque Country to Andalucia Explorer - North to South

            Guided Road Cycling Holiday

            Duration

            21 days

            Prices from

            £5,195 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.
            30/08/2026
            Last Spaces
            19/09/2026£5,195.00
            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
            Italy

            Grand Traverse Explorer - South to North

            Guided Road Cycling Holiday

            Duration

            22 days

            Prices from

            £5,495 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.
            29/08/2026
            Guaranteed
            19/09/2026£5,495.00
            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
            United Kingdom

            Land's End to John O'Groats Explorer

            Guided Road Cycling Holiday

            Duration

            22 days

            Prices from

            £4,895 P.P.
            View Reviews
            25
            1
            2
            3
            4
            5
            Grade 3 - 4: Moderate/ Challenging
            More Info BOOK NOW

            Land's End to John O'Groats Explorer

            Guided Road 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.
            11/07/2026
            Last Spaces
            01/08/2026£4,895.00
            05/09/2026
            Last Spaces
            26/09/2026£4,895.00
            08/05/202729/05/2027£5,045.00
            05/06/202726/06/2027£5,045.00
            03/07/202724/07/2027£5,045.00
            31/07/202721/08/2027£5,045.00
            • Ride the length of Britain from toe to tip and declare yourself an ‘End to Ender’
            • Experience the regional changes in tradition, culture and accents as you progress from county to county
            • Enjoy spectacular scenery from Cheddar Gorge to the Cairngorms
            • 3 countries in 19 days of riding
            • 1,000 miles of Britain at its best
            • Cornish pasties to haggis and everything in between
            Photo Highlights Dates
            Guided
            Guided
            France

            Corsica - The Beautiful Isle

            Guided Road Cycling Holiday

            Duration

            8 days

            Prices from

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

            Corsica - The Beautiful Isle

            Guided Road Cycling Holiday

            Start DateEnd DatePrice p.p.
            12/09/2026
            Guaranteed
            19/09/2026£2,395.00
            15/05/202722/05/2027£2,495.00
            18/09/202725/09/2027£2,495.00
            • One of the most dramatic coastal rides in Europe
            • The descent through the Scala di Santa Regina between the Col de Vergio and Corte
            • Chestnut beers all round in Corte, the ancient and rustic mountain capital
            • Mouthwatering local cuisine, charcuterie and cheeses
            • The Castagniccia – Corsica’s most unspoiled region of chestnut forest, wild boar and traditional rural villages
            Photo Highlights Dates
            Guided
            Guided
            Italy

            NEW! - Piedmont - La Strada del Vino

            Guided Road Cycling Holiday

            Duration

            8 days

            Prices from

            £1,995 P.P.
            View Reviews
            4
            1
            2
            3
            4
            5
            Grade 3 : Moderate
            More Info BOOK NOW

            NEW! - Piedmont - La Strada del Vino

            Guided Road Cycling Holiday

            Start DateEnd DatePrice p.p.
            12/09/202619/09/2026£1,995.00
            01/05/202708/05/2027£2,075.00
            05/06/202712/06/2027£2,075.00
            25/09/202702/10/2027£2,075.00
            • Cycling through rolling hills terraced with vineyards and quaint medieval villages
            • Capturing beautiful views that stretch as far as the Alps
            • Admiring castle topped villages which lend a historic romantic feel to the area
            • Tasting some of the best wines in Italy in the regions they are produced; Barolo, Barbaresco and Asti
            • Feasting on some of the best regional food in Italy, including truffles, cheeses and hazelnut Gianduia chocolates!
            Photo Highlights Dates
            Guided
            Guided
            Spain

            Bilbao to Barcelona

            Guided Road Cycling Holiday

            Duration

            10 days

            Prices from

            £2,995 P.P.
            View Reviews
            2
            1
            2
            3
            4
            5
            Grade 3 - 4: Moderate/ Challenging
            More Info BOOK NOW

            Bilbao to Barcelona

            Guided Road Cycling Holiday

            Start DateEnd DatePrice p.p.
            03/09/2026
            Last Spaces
            12/09/2026£2,995.00
            24/09/2026
            Last Spaces
            03/10/2026£2,995.00
            12/05/202721/05/2027£3,085.00
            03/09/202712/09/2027£3,085.00
            25/09/202704/10/2027£3,085.00
            • An epic coast to coast adventure – riding all the way from the Atlantic to the Med under your own steam
            • Cycling with the impressive back-drop of the Pyrenees by your side
            • Dining each evening on rustic Spanish mountain cuisine
            • The striking pink granite of the Parc Natural de Montserrat
            • Dramatic castles, forts and monasteries perched on every hilltop
            • Seeing Barcelona stretched out in front of you, with the sea beyond
            Photo Highlights Dates
            Guided
            Guided
            Spain

            Sierra Nevada and Granada

            Guided Road Cycling Holiday

            Duration

            7 days

            Prices from

            £1,985 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 Cycling Holiday

            Start DateEnd DatePrice p.p.
            18/10/2026
            Guaranteed
            24/10/2026£1,985.00
            03/05/202709/05/2027£1,995.00
            20/10/202726/10/2027£1,995.00
            • 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
            Scotland

            Scotland - Tour d'Ecosse

            Guided Road Cycling Holiday

            Duration

            8 days

            Prices from

            £1,855 P.P.
            View Reviews
            6
            1
            2
            3
            4
            5
            Grade 3 : Moderate
            More Info BOOK NOW

            Scotland - Tour d'Ecosse

            Guided Road Cycling Holiday

            Start DateEnd DatePrice p.p.
            04/07/2026
            Fully Booked
            11/07/2026£1,855.00
            08/08/2026
            Last Spaces
            15/08/2026£1,855.00
            05/09/2026
            Last Spaces
            12/09/2026£1,855.00
            08/05/202715/05/2027£1,925.00
            26/06/202703/07/2027£1,925.00
            07/08/202714/08/2027£1,925.00
            04/09/202711/09/2027£1,925.00
            • Quiet single-track roads for miles on end
            • Bealach Na Ba – the greatest road ascent in the UK
            • Feasting on fresh seafood after a day in the saddle
            • Stunning views out over the Isle of Skye
            • Cycling the peaceful lochside roads of Scotland
            • The swooping coastal road from Ullapool to Kinlochewe
            Photo Highlights Dates
            Guided
            Guided
            United Kingdom

            Eden Valley and the North Pennines

            Guided Road Cycling Holiday

            Duration

            6 days

            Prices from

            £1,095 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 Cycling Holiday

            Start DateEnd DatePrice p.p.
            26/07/2026
            Fully Booked
            31/07/2026£1,095.00
            20/09/202625/09/2026£1,095.00
            • 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
            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
            • 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
            • 1
            • 2
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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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