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            2026 Cycling Holidays To Book Now

            We found 46 Holidays in your search for:

            Destinations (81)
            Types of Cycling / Grades (7)
            Departure Month

            2025

            2026

            2027

            Level of Support

            We found 46 Holidays in your search for:

            Select Order Order By
            Destinations (81)
            Types of Cycling / Grades (7)
            Departure Month

            2025

            2026

            2027

            Level of Support

            The results are in! These were our best selling trips for 2025 that you'd be wise to book early for 2026. Take your pick from popular road cycling challenges to relaxing rides through the English countryside and off-road adventures in Spain and Italy.

            We are also working on NEW routes and destinations for 2026. Be the first to find out more by signing up for our newsletter.

            • All Cycling Holidays
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            Page 3 of 5

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            Guided
            Guided
            Costa Rica

            Ruta de los Volcanes

            Guided Road Cycling Holiday

            Duration

            13 days

            Prices from

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

            Ruta de los Volcanes

            Guided Road Cycling Holiday

            Start DateEnd DatePrice p.p.
            22/12/202503/01/2026£4,295.00
            14/03/202626/03/2026£4,295.00
            22/12/202603/01/2027£4,395.00
            13/03/202725/03/2027£4,425.00
            22/12/202703/01/2028£4,525.00
            • Spotting an unparalleled diversity of wildlife
            • Cycling in the shadow of palm trees along the Pacific coast
            • Breaking through the clouds as we cross Costa Rica’s central mountains
            • Enjoying volcanic vistas over a drink in La Fortuna
            • Watching the sun go down from Samara beach after a rewarding day in the saddle
            • The change in scenery on opposing sides of the continental divide
            Photo Highlights Dates
            Guided
            Guided
            United Kingdom

            Land's End to John O'Groats Classic

            Guided Road Cycling Holiday

            Duration

            16 days

            Prices from

            £3,565 P.P.
            View Reviews
            20
            1
            2
            3
            4
            5
            Grade 3 - 4: Moderate/ Challenging
            More Info BOOK NOW

            Land's End to John O'Groats Classic

            Guided Road Cycling Holiday

            Start DateEnd DatePrice p.p.
            * 23/08/2025
            Guaranteed
            07/09/2025£3,395.00
            23/05/202607/06/2026£3,565.00
            22/08/202606/09/2026£3,565.00
            • 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 14 days of riding
            • 1,000 miles of Britain at its best
            • Cornish pasties to haggis and everything in between
            Photo Highlights Dates
            Guided
            Guided
            Italy

            Grand Traverse Classic - North to South

            Guided Road Cycling Holiday

            Duration

            17 days

            Prices from

            £4,395 P.P.
            View Reviews
            9
            1
            2
            3
            4
            5
            Grade 4 : Challenging
            More Info BOOK NOW

            Grand Traverse Classic - North to South

            Guided Road Cycling Holiday

            Start DateEnd DatePrice p.p.
            25/09/2025
            Last Spaces
            11/10/2025£4,395.00
            21/05/202606/06/2026£4,615.00
            24/09/202610/10/2026£4,615.00
            • Riding down 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: Lucca, San Gimignano, Pienza, Assisi and Lecce
            • 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 to the most southerly point of Italy, having ridden nearly 1,100 miles and climbed over 21,000 metres!
            Photo Highlights Dates
            Guided
            Guided
            Scotland

            Scotland - Hebridean Way

            Guided Leisure Cycling Holiday

            Duration

            7 days

            Prices from

            £2,425 P.P.
            View Reviews
            10
            1
            2
            3
            4
            5
            Grade 3-4 : Moderate/Active
            More Info BOOK NOW

            Scotland - Hebridean 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. 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.
            * 31/08/2025
            Fully Booked
            06/09/2025£2,425.00
            03/05/202609/05/2026£2,555.00
            24/05/202630/05/2026£2,555.00
            31/05/202606/06/2026£2,555.00
            21/06/202627/06/2026£2,555.00
            05/07/202611/07/2026£2,555.00
            26/07/202601/08/2026£2,555.00
            16/08/202622/08/2026£2,555.00
            30/08/202605/09/2026£2,555.00
            • Riding along the Golden Road
            • Miles and miles of picture-perfect white sand beaches
            • Enjoying a wee dram from the Distillery at Tarbert
            • Seeing the traditional weaving of Harris Tweed
            • Views of Luskentyre Beach over a delicious picnic lunch
            • Visiting the Blackhouse Village at Gearrannan
            • The awe inspiring Callanish Standing Stones
            Photo Highlights Dates
            Guided
            Guided
            Norway

            Classic Fjords

            Guided Road Cycling Holiday

            Duration

            9 days

            Prices from

            £4,795 P.P.
            View Reviews
            3
            1
            2
            3
            4
            5
            Grade 3 : Moderate
            More Info BOOK NOW

            Classic Fjords

            Guided Road Cycling Holiday

            Start DateEnd DatePrice p.p.
            13/06/202621/06/2026£4,795.00
            29/08/202606/09/2026£4,795.00
            • The natural beauty of the Norwegian landscape, fjords, mountains, waterfalls and coastlines
            • Narrow and dramatic Norangsdalen Valley & the beautiful coastal roads of Hjørundfjorden
            • Scenic, pollution-free, quiet roads and the freshest, cleanest air you can breathe
            • Cycling the shores of world-famous Sognefjord and beautiful Balestrand
            • Trollstigen Pass (The Troll’s Ladder) Norway’s most spectacular mountain road
            • Cruising along the UNESCO listed Geirangerfjord by ferry
            • Ålesund, Norway’s most beautiful city showcasing its impressive Art Nouveau architecture
            Photo Highlights Dates
            Guided
            Guided
            United Kingdom

            Norfolk - Rebellion Way

            Guided Leisure Cycling Holiday

            Duration

            7 days

            Prices from

            £1,595 P.P.
            View Reviews
            8
            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. 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.
            21/09/2025
            Fully Booked
            27/09/2025£1,595.00
            26/04/202602/05/2026£1,675.00
            05/07/202611/07/2026£1,675.00
            09/08/202615/08/2026£1,675.00
            06/09/202612/09/2026£1,675.00
            • 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
            Cuba

            Cuban Revolutions

            Guided Cycling Holiday

            Duration

            15 days

            Prices from

            £3,445 P.P.
            View Reviews
            24
            1
            2
            3
            4
            5
            Grade 2 - 3: Gentle/ Moderate
            More Info BOOK NOW

            Cuban Revolutions

            Guided Cycling Holiday

            Start DateEnd DatePrice p.p.
            08/11/202522/11/2025£3,445.00
            22/11/202506/12/2025£3,445.00
            24/01/202607/02/2026£3,635.00
            07/02/202621/02/2026£3,635.00
            07/11/202621/11/2026£3,635.00
            21/11/202605/12/2026£3,635.00
            • Kicking back with a post-ride Mojito
            • Cycling around the loaf-shaped mountains of Viñales
            • Exploring the cultural delights of Trinidad and Santiago
            • Cuban salsa beats in downtown Havana
            • Stories of Che, Castro and the Revolution
            • Cycling the Caribbean coast of Marea del Portillo
            Photo Highlights Dates
            Guided
            Guided
            Italy

            NEW! Coast to Coast - Puglia to Cilento

            Guided Road Cycling Holiday

            Duration

            8 days

            Prices from

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

            NEW! Coast to Coast - Puglia to Cilento

            Guided Road Cycling Holiday

            Start DateEnd DatePrice p.p.
            28/09/2025
            Last Spaces
            05/10/2025£1,995.00
            06/10/2025
            Last Spaces
            13/10/2025£1,995.00
            18/04/202625/04/2026£2,095.00
            26/04/202603/05/2026£2,095.00
            27/09/202604/10/2026£2,095.00
            • An epic coast to coast journey through southern Italy riding from the Adriatic coast to the Tyrrhenian Sea
            • Exploring the UNESCO World Heritage sites of Alberobello, Matera, Padula and Paestum
            • Losing ourselves in the labyrinthic white washed alleyways of Noci and Tricarico
            • Climbing the hills of little-known Basilicata, to the hill-top villages of Castelmezzano, Calvello and Marsico Vetere
            • Cycling through the Dolomiti Lucane, southern Italy’s lesser-known Dolomites
            • Enjoying the roller-coaster ride along the Cilento Coast from Palinuro to Paestum
            • Sampling southern Italy’s best food and wine
            Photo Highlights Dates
            Guided
            Guided
            France

            Alps - Mont Ventoux to Alpe d'Huez

            Guided Road Cycling Holiday

            Duration

            8 days

            Prices from

            £2,620 P.P.
            View Reviews
            9
            1
            2
            3
            4
            5
            Grade 4 : Challenging
            More Info BOOK NOW

            Alps - Mont Ventoux to Alpe d'Huez

            Guided Road Cycling Holiday

            Start DateEnd DatePrice p.p.
            14/06/202621/06/2026£2,620.00
            16/08/202623/08/2026£2,620.00
            • Legendary Tour de France challenges every day
            • ‘Warming up’ on Mont Ventoux, the ‘Giant of Provence’
            • Blue skies, fresh air and snow-capped peaks
            • ‘Top of the world’ sensations on the summit of the Izoard
            • Ticking off lots of Tour de France classics
            • Riding through Provençal lavender flelds, synonymous with the region
            • The final challenge of the legendary Alpe d‘Huez
            Photo Highlights Dates
            Guided
            Guided
            Scotland

            Scotland - Tour d'Ecosse

            Guided Road Cycling Holiday

            Duration

            8 days

            Prices from

            £1,765 P.P.
            View Reviews
            7
            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.
            30/08/2025
            Last Spaces
            06/09/2025£1,765.00
            02/05/202609/05/2026£1,855.00
            23/05/202630/05/2026£1,855.00
            13/06/202620/06/2026£1,855.00
            04/07/202611/07/2026£1,855.00
            08/08/202615/08/2026£1,855.00
            05/09/202612/09/2026£1,855.00
            • 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
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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
            One of the very best trips! The kindness and professionalism of the lead guide and his locally based colleagues was outstanding in every respect.
            Brenda, Italy - Dolomites of Brenta, Guided Mountain Bike Holiday
            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
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