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            2027 Cycling Holidays You Can Book Now

            We found 39 Holidays in your search for:

            Destinations (82)
            Types of Cycling / Grades (7)
            Departure Month

            2026

            2027

            2028

            Level of Support

            We found 39 Holidays in your search for:

            Select Order Order By
            Destinations (82)
            Types of Cycling / Grades (7)
            Departure Month

            2026

            2027

            2028

            Level of Support
            2027 Road Cycling Holidays 2027 Adventure Cycling Holidays 2027 Leisure Cycling Holidays 2027 Mountain Bike Holidays

            Planning ahead for your dream cycling holiday? Whether you're training to complete the UK's ultimate challenge ride - Land's End to John o' Groats - or searching for your trip of a lifetime in a far-flung destination, we know it’s helpful to plan ahead. These tours all have 2027 dates available to book now. Plus, you’ll only need to pay a deposit upfront to secure your space.

            What are you waiting for? Stop dreaming and start planning!

            • All Cycling Holidays
            • BOOK EARLY

            Page 4 of 4

            Select Order Order By
            Guided
            Guided
            Sri Lanka

            Backroads and Beaches

            Guided Cycling Holiday

            Duration

            15 days

            Prices from

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

            Backroads and Beaches

            Guided Cycling Holiday

            Start DateEnd DatePrice p.p.
            07/11/2026
            Last Spaces
            21/11/2026£2,895.00
            13/02/202727/02/2027£2,895.00
            06/11/202720/11/2027£2,895.00
            • Eying up the elephants at Udawalawe
            • Stunning Sigirya and the Lion Rock
            • Colonial cool in Nuwara Eliya
            • Coastal cycling and beautiful beaches
            • Honing in on Horton Plains after a day in the hills
            • The Knuckles and Kandy’s Temple of the Tooth
            Photo Highlights Dates
            Guided
            Guided
            Peru

            Sacred Valley of the Incas

            Guided Cycling Holiday

            Duration

            12 days

            Prices from

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

            Sacred Valley of the Incas

            Guided Cycling Holiday

            Start DateEnd DatePrice p.p.
            06/06/2026
            Guaranteed
            17/06/2026£2,895.00
            15/08/202626/08/2026£2,895.00
            19/09/2026
            Guaranteed
            30/09/2026£2,895.00
            05/06/202716/06/2027£3,035.00
            14/08/202725/08/2027£3,035.00
            18/09/202729/09/2027£3,035.00
            • 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
            Czech Republic, Austria, Slovenia & Italy

            Prague to Venice

            Guided Road Cycling Holiday

            Duration

            21 days

            Prices from

            £5,775 P.P.
            View Reviews
            1
            1
            2
            3
            4
            5
            Grade 3 : Moderate
            More Info BOOK NOW

            Prague to Venice

            Guided Road Cycling Holiday

            Start DateEnd DatePrice p.p.
            06/06/2026
            Last Spaces
            26/06/2026£5,775.00
            04/07/2026
            Fully Booked
            24/07/2026£5,775.00
            01/08/2026
            Fully Booked
            21/08/2026£5,775.00
            05/06/2027
            Last Spaces
            25/06/2027£6,195.00
            03/07/202723/07/2027£6,195.00
            31/07/202720/08/2027£6,195.00
            • A journey from Central Europe to the Mediterranean through four European countries
            • Visit the vibrant capitals of Prague, Vienna and Ljubljana
            • Learn about the historical Central European regions of Bohemia and Styria
            • Explore the UNESCO World Heritage sites of Prague, Cesky Krumlov, Vienna, Graz, and Venice
            • Have a well deserved end-of-ride pilsner seated in the village square of a little Bohemian village
            • Enjoy quiet countryside roads with sweeping views all the way from Prague to Venice
            • Staying in quality accommodation, with warm traditional hospitality
            • Feast on the traditional dishes, desserts and drinks of the Czech, Austrian and Slovenian cuisine.
            Photo Highlights Dates
            Guided
            Guided
            Mongolia

            Route of the Nomads

            Guided Cycling Holiday

            Duration

            16 days

            Prices from

            £3,195 P.P.
            View Reviews
            9
            1
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            3
            4
            5
            Grades 3 - 4: Moderate/ Active
            More Info BOOK NOW

            Route of the Nomads

            Guided Cycling Holiday

            Start DateEnd DatePrice p.p.
            06/06/202621/06/2026£3,195.00
            12/07/2026
            Guaranteed
            27/07/2026£3,195.00
            05/06/202720/06/2027£3,355.00
            10/07/202725/07/2027£3,355.00
            • The Palace of Bogd Khan & Ganden Monastery – Ulaan Baatar
            • Tsetserleg Hot Springs & time at a traditional Ger camp
            • Gorgeous Tamir River Valley & Orkhon Valley Falls
            • Delicious food and nights under the stars
            • Cycling through one of the world’s true wildernesses
            • Nomadic horsemen and smiling children along the way
            Photo Highlights Dates
            Guided
            Guided
            Eswatini (Swaziland)

            Cycling Safari

            Guided Cycling Holiday

            Duration

            11 days

            Prices from

            £3,415 P.P.
            View Reviews
            7
            1
            2
            3
            4
            5
            Grade 3 : Moderate
            More Info BOOK NOW

            Cycling Safari

            Guided Cycling Holiday

            Start DateEnd DatePrice p.p.
            20/08/2026
            Last Spaces
            30/08/2026£3,415.00
            08/10/202618/10/2026£3,415.00
            01/04/202711/04/2027£3,655.00
            19/08/202729/08/2027£3,655.00
            07/10/202717/10/2027£3,655.00
            • Explore the diverse regions of this amazing country
            • Experience some fantastic ‘off the beaten path’ cycling
            • Stay in amazing accommodation, full of character
            • Discover an incredible range of wildlife
            • Sample a wide range of great local food
            • Get to know the super-friendly local people
            Photo Highlights Dates
            Guided
            Guided
            Borneo

            Secret Sarawak

            Guided Cycling Holiday

            Duration

            14 days

            Prices from

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

            Secret Sarawak

            Guided Cycling Holiday

            Start DateEnd DatePrice p.p.
            09/05/202622/05/2026£2,995.00
            22/08/202604/09/2026£2,995.00
            26/09/2026
            Guaranteed
            09/10/2026£2,995.00
            08/05/202721/05/2027£3,145.00
            21/08/202703/09/2027£3,145.00
            25/09/202708/10/2027£3,145.00
            • Orangutan spotting at Semenggoh Nature Reserve
            • Overnighting at a traditional Sarawak Longhouse
            • Wildlife walks at Bako National Park
            • Stunning Sematan and cycling its palm fringed coastline
            • Kayaking through scenic rainforest
            • Siniawan’s market and its street food delights
            Photo Highlights Dates
            Guided
            Guided
            South Africa

            NEW! Western Cape - Coast and Winelands

            Guided Cycling Holiday

            Duration

            11 days

            Prices from

            £4,675 P.P.
            1
            2
            3
            4
            5
            Grade 3 : Moderate
            More Info BOOK NOW

            NEW! Western Cape - Coast and Winelands

            Guided Cycling Holiday

            Start DateEnd DatePrice p.p.
            25/10/202604/11/2026£4,675.00
            11/04/202721/04/2027£5,145.00
            17/10/202727/10/2027£5,145.00
            • Riding through the tracks and quiet roads of the cape winelands
            • Watching the comical penguins, lounging seals and perhaps even breaching whales
            • Cycling the dramatic coastal roads of Chapman’s Peak and Clarence Drive
            • Taking in the stunning views at the top of Franschhoek Pass
            • Pausing for a glass of the local vintage
            • Incredible views framed by the unique fynbos vegetation
            Photo Highlights Dates
            Guided
            Guided
            Chile and Argentina

            Lake District

            Guided Cycling Holiday

            Duration

            13 days

            Prices from

            £4,215 P.P.
            View Reviews
            47
            1
            2
            3
            4
            5
            Grade 3 : Moderate
            More Info BOOK NOW

            Lake District

            Guided Cycling Holiday

            Start DateEnd DatePrice p.p.
            11/10/202623/10/2026£4,215.00
            06/12/202618/12/2026£4,215.00
            10/01/202722/01/2027£4,215.00
            • Majestic Volcan Osorno and its snow-capped peak
            • Tasting the chocolates of Bariloche
            • Biking the Seven Lakes Route to San Martin de los Andes
            • The monkey-puzzle tree forests of Conguillio
            • Sampling a tasty Malbec or Carmanere after a day’s biking
            • Hiking the lofty heights of Volcan Villarica
            Photo Highlights Dates
            Guided
            Guided
            Jordan

            Petra, Wadi Rum & The Dead Sea

            Guided Cycling Holiday

            Duration

            8 days

            Prices from

            £2,095 P.P.
            View Reviews
            9
            1
            2
            3
            4
            5
            Grade 3 : Moderate
            More Info BOOK NOW

            Petra, Wadi Rum & The Dead Sea

            Guided Cycling Holiday

            Start DateEnd DatePrice p.p.
            17/10/202624/10/2026£2,095.00
            28/11/202605/12/2026£2,095.00
            13/03/202720/03/2027£2,195.00
            24/04/202701/05/2027£2,195.00
            16/10/202723/10/2027£2,195.00
            27/11/202704/12/2027£2,195.00
            • Discovering Jerash – the most well-preserved Roman city, outside of Rome
            • Exploring Petra – The Red Rose City
            • Cycling Jordan’s deserts & dramatic canyons
            • Desert star gazing in the dramatic Wadi Rum
            • Dead Sea dipping and your very own DIY spa treatment
            • Bedouin hospitality and feasting on delicious local food
            • Crusader castles & the historic city of Amman
            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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