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            Bestsellers - 2027 Holidays to Book Now

            We found 49 Holidays in your search for:

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

            2026

            2027

            2028

            Level of Support

            We found 49 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

            Some trips are best reserved early before they fill up. Now that our 2027 dates are live, we've pulled together a handy list so you don't miss out. Take your pick from popular road cycling challenges to e-bike rides through the Tuscan countryside and off-road adventures in Spain and Italy. And if nothing in the most popular list takes your fancy, you'll find 2027 dates up across our cycling ranges, so go on, have a browse and book with a deposit today!

            • All Cycling Holidays
            • BOOK EARLY

            Page 5 of 5

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            Guided
            Guided
            Scotland

            Scotland - Lochs and Glens

            Guided Leisure Cycling Holiday

            Duration

            7 days

            Prices from

            £1,655 P.P.
            View Reviews
            4
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            Grade 3-4 : Moderate/Active
            More Info BOOK NOW

            Scotland - Lochs and Glens

            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.
            09/05/202715/05/2027£1,655.00
            13/06/202719/06/2027£1,655.00
            15/08/202721/08/2027£1,655.00
            • Watching the sun rise over Loch Lomond
            • The beautiful lochs of Venachar, Lubnaig and Tay
            • Cycling through the dramatic Cairngorms National Park
            • Scottish wildlife at its best including deer, red squirrels, eagles and osprey
            • Castles and distilleries galore
            • Rural Scottish cycling at its very best
            Photo Highlights Dates
            Guided
            Guided
            Spain

            Basque Country to Andalucia Explorer - North to South

            Guided Road Cycling Holiday

            Duration

            21 days

            Prices from

            £5,355 P.P.
            View Reviews
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            Grade 3 : Moderate
            More Info BOOK NOW

            Basque Country to Andalucia Explorer - North to South

            Guided Road Cycling Holiday

            Start DateEnd DatePrice p.p.
            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
            India

            Classic Kerala

            Guided Cycling Holiday

            Duration

            14 days

            Prices from

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

            Classic Kerala

            Guided Cycling Holiday

            Start DateEnd DatePrice p.p.
            21/11/2026
            Guaranteed
            04/12/2026£2,415.00
            31/01/2027
            Fully Booked
            13/02/2027£2,415.00
            30/10/202712/11/2027£2,495.00
            30/01/202812/02/2028£2,535.00
            29/10/202811/11/2028£2,625.00
            • Cycling through lush tea and spice plantations
            • Periyar wildlife reserve, home to elephants, bison and tigers
            • Climbing through cool air and pristine forests
            • Drifting on a rice barge through Kerala’s backwaters
            • Relaxing on white sands of Marari Beach
            • Enjoying the best of Southern Indian Cuisine
            Photo Highlights Dates
            Guided
            Guided
            Spain

            Ruta de la Plata - Seville to Santiago

            Guided Gravel Riding Holiday

            Duration

            16 days

            Prices from

            £4,595 P.P.
            View Reviews
            2
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            Grade 3-4 : Moderate/Challenging
            More Info BOOK NOW

            Ruta de la Plata - Seville to Santiago

            Guided Gravel Riding Holiday

            Start DateEnd DatePrice p.p.
            04/10/2026
            Contact Us
            19/10/2026£4,595.00
            24/04/202709/05/2027£4,695.00
            03/10/202718/10/2027£4,695.00
            • Biking through 4 diverse regions and 7 provinces of Spain
            • Delicious, regional cuisine
            • Sampling a diverse range of trails and paths
            • Exploring historic Roman roads and viaducts
            • 1,000km of challenging linear riding through ever changing landscapes
            • Crossing high passes and endless thrilling descents
            • Arriving in the beautiful Santiago de Compostela at the end of our journey
            Photo Highlights Dates
            Guided
            Guided
            France

            St Malo to Nice Classic

            Guided Road Cycling Holiday

            Duration

            15 days

            Prices from

            £4,525 P.P.
            View Reviews
            15
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            Grade 3 - 4: Moderate/ Challenging
            More Info BOOK NOW

            St Malo to Nice Classic

            Guided Road Cycling Holiday

            Start DateEnd DatePrice p.p.
            18/06/202702/07/2027£4,525.00
            13/08/202727/08/2027£4,525.00
            • Cycling along the Brittany coast with views out to the Abbey of Mont St Michel
            • Travelling under your own power all the way from the Channel to the Mediterranean
            • Following riverside roads along the Loire, Dordogne and the Rhône
            • Riding through the wine drenched Châteauneuf-du-Pape!
            • Riding through the lavender fields of Provence and winding your way through the Verdon Gorge
            • Descending to Nice to ride along the Promenade des Anglais like a Tour de France winner!
            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
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            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
            Japan

            Fuji to Kyoto

            Guided Cycling Holiday

            Duration

            12 days

            Prices from

            £5,495 P.P.
            View Reviews
            2
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            Grade 3 : Moderate
            More Info BOOK NOW

            Fuji to Kyoto

            Guided Cycling Holiday

            Start DateEnd DatePrice p.p.
            08/11/2026
            Guaranteed
            19/11/2026£5,595.00
            22/11/202603/12/2026£5,595.00
            11/04/202722/04/2027£5,495.00
            07/11/202718/11/2027£5,595.00
            • Majestic Mt. Fuji and lovely Lake Kawaguchi
            • Exploring Nagahama and the awesome Hikone Castle
            • Hatage Onsen and its soothing effects after a day’s cycling
            • Bullet Trains and Bento boxes
            • Taking in colourful Kyoto
            • Peaceful pedalling and rural riding
            Photo Highlights Dates
            Guided
            Guided
            Morocco

            Road Atlas

            Guided Road Cycling Holiday

            Duration

            10 days

            Prices from

            £1,895 P.P.
            View Reviews
            30
            1
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            3
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            Grade 3 : Moderate
            More Info BOOK NOW

            Road Atlas

            Guided Road Cycling Holiday

            Start DateEnd DatePrice p.p.
            07/11/2026
            Fully Booked
            16/11/2026£1,895.00
            27/12/202605/01/2027£1,895.00
            30/01/202708/02/2027£1,995.00
            06/11/202715/11/2027£1,995.00
            27/12/202705/01/2028£1,995.00
            • The High Atlas mountain range
            • The outstanding Ounila Valley and Ait Benhaddou Kasbah
            • Exploring the surreal blue rocks of Tafraoute
            • The incredible 100km ride from Tafraoute towards the coast
            • Enjoying a cold beer on one of Morocco’s finest terraces at Immouzer
            • The sights, smells and sounds of the Marrakech souk
            • Starting and finishing in this years ‘Capital of Culture’ Marrakech
            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
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            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£2,095.00
            27/11/202704/12/2027£2,095.00
            18/03/202825/03/2028£2,195.00
            25/11/202802/12/2028£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
            • Previous page
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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

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            September 4, 2026
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            The majestic Pyrenees mountain range, forming a natural border between France and Spain, has long attracted cyclists seeking both challenge and charm. Cycling in the Pyrenees offers exhilarating road cycling adventures, with stunning landscapes, diverse climates, and rich culture to discover. Skedaddle offers two distinct road cycling holidays through this rugged terrain. The Trans Pyrenees ...

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            September 4, 2026

            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

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