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            Bestsellers - 2027 Holidays to Book Now

            We found 49 Holidays in your search for:

            Destinations (83)
            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 (83)
            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 4 of 5

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            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
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            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
            09/01/2027
            Last Spaces
            23/01/2027£2,895.00
            13/02/2027
            Fully Booked
            27/02/2027£2,895.00
            14/03/202728/03/2027£2,895.00
            06/11/202720/11/2027£2,895.00
            12/02/202826/02/2028£2,895.00
            04/11/202818/11/2028£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
            Italy

            Tuscany - Strade Bianche Explorer

            Guided Gravel Riding Holiday

            Duration

            8 days

            Prices from

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

            Tuscany - Strade Bianche Explorer

            Guided Gravel Riding Holiday

            Start DateEnd DatePrice p.p.
            24/04/202701/05/2027£2,295.00
            08/05/202715/05/2027£2,295.00
            25/09/202702/10/2027£2,295.00
            • Riding some of the classic Tuscany gravel routes including the Strade Bianche
            • Cycling through the historic wine regions of Tuscany, stopping off for a bit of wine tasting
            • Exploring the region on a mix of terrains
            • Riding the stunning UNESCO heritage region of Val d’Orcia
            • Relaxing in small villages for a coffee with the locals
            • Easing along the rolling hills of the ‘Colli Sienesi’
            • Chilling out with a post-ride Chianti or Brunello
            Photo Highlights Dates
            Guided
            Guided
            United Kingdom

            Land's End to John O'Groats Explorer

            Guided Electric Bike Holiday

            Duration

            22 days

            Prices from

            £5,045 P.P.
            View Reviews
            2
            1
            2
            3
            4
            5
            Grade 3-4 : Moderate/Active
            More Info BOOK NOW

            Land's End to John O'Groats Explorer

            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.
            17/04/2027
            Guaranteed
            08/05/2027£5,045.00
            19/06/2027
            Last Spaces
            10/07/2027£5,045.00
            11/09/202702/10/2027£5,045.00
            • 3 countries in 19 days of riding
            • 1,000 miles of Britain at its best – Riding an e-bike the length of Britain from toe to tip and declaring yourself an ‘End to Ender’
            • Cornish pasties to haggis and everything in between
            • Experiencing the regional changes in tradition, culture and accents as you progress from county to county
            • Enjoying spectacular scenery from Cheddar Gorge to the Cairngorms
            Photo Highlights Dates
            Guided
            Guided
            Spain

            Andalucia - Costa de La Luz and Cadiz Discoverer

            Guided Gravel Riding Holiday

            Duration

            8 days

            Prices from

            £2,195 P.P.
            View Reviews
            1
            1
            2
            3
            4
            5
            Grade 2-3: Gentle/Moderate
            More Info BOOK NOW

            Andalucia - Costa de La Luz and Cadiz Discoverer

            Guided Gravel Riding Holiday

            Start DateEnd DatePrice p.p.
            24/10/2026
            Fully Booked
            31/10/2026£2,195.00
            29/03/202705/04/2027£2,225.00
            24/10/202731/10/2027£2,225.00
            • Enjoying Andalucia’s extensive network of non-technical, coastal gravel riding
            • Riding cyclepaths, 4×4 tracks, asphalt lanes, earthy singletrack and sandy trails
            • Experiencing vibrant Tarifa; The gateway to 2 continents
            • Discovering the coast of light’s wild and rugged coastline with huge expansive white sand beaches and traditional fishing villages
            • Indulging in delicious local seafood and local wines and sherries
            • Exploring the lanes of fun-loving Cadiz for the best tapas and flamenco
            • Savouring a glass of sherry in a historic bodega within the Sherry Triangle
            Photo Highlights Dates
            Guided
            Guided
            United Kingdom

            Land's End to John O'Groats Explorer

            Guided Road Cycling Holiday

            Duration

            22 days

            Prices from

            £5,045 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.
            08/05/2027
            Guaranteed
            29/05/2027£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
            Costa Rica

            Ruta de los Volcanes

            Guided Road Cycling Holiday

            Duration

            13 days

            Prices from

            £4,395 P.P.
            View Reviews
            13
            1
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            3
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            Grade 3 : Moderate
            More Info BOOK NOW

            Ruta de los Volcanes

            Guided Road Cycling Holiday

            Start DateEnd DatePrice p.p.
            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
            Czech Republic, Austria, Slovenia & Italy

            Prague to Venice

            Guided Road Cycling Holiday

            Duration

            21 days

            Prices from

            £6,195 P.P.
            View Reviews
            5
            1
            2
            3
            4
            5
            Grade 3 : Moderate
            More Info BOOK NOW

            Prague to Venice

            Guided Road Cycling Holiday

            Start DateEnd DatePrice p.p.
            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
            France

            St Malo to Nice Explorer

            Guided Road Cycling Holiday

            Duration

            20 days

            Prices from

            £6,075 P.P.
            View Reviews
            19
            1
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            3
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            Grade 3 : Moderate
            More Info BOOK NOW

            St Malo to Nice Explorer

            Guided Road Cycling Holiday

            Start DateEnd DatePrice p.p.
            25/05/202713/06/2027£6,075.00
            06/09/2027
            Last Spaces
            25/09/2027£6,075.00
            • Visiting the enchanting medieval village of Roccamadour clinging to the steep cliff side ; exploring the romanic abbey and its affrescoed caves in the little town of Bratome on the River Dronne
            • Travelling under your own power all the way from the Channel to the Mediterranean
            • Meandering along the Loire, Dordogne and Rhône rivers
            • Riding through vineyards of Chateauneuf-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
            Photo Highlights Dates
            Guided
            Guided
            Vietnam

            Mountains and Coast

            Guided Cycling Holiday

            Duration

            15 days

            Prices from

            £2,095 P.P.
            View Reviews
            19
            1
            2
            3
            4
            5
            Grade 3 : Moderate
            More Info BOOK NOW

            Mountains and Coast

            Guided Cycling Holiday

            Start DateEnd DatePrice p.p.
            14/11/202628/11/2026£2,165.00
            14/02/202728/02/2027£2,095.00
            06/03/202720/03/2027£2,095.00
            13/11/202727/11/2027£2,095.00
            12/02/202826/02/2028£2,095.00
            04/03/202818/03/2028£2,095.00
            11/11/202825/11/2028£2,095.00
            • Exploring the lesser visited parts of Vietnam by bike
            • Stunning Saigon – the ‘Pearl of the Orient’
            • Heading off the tourist trail in the Central Highlands
            • Treating your tastebuds to Vietnam’s legendary cuisine
            • Get your caffeine hit with a fresh roadside brew
            • Soaking up the sunshine at beautiful Nha Trang
            Photo Highlights Dates
            Guided
            Guided
            Italy

            Grand Traverse Explorer - South to North

            Guided Road Cycling Holiday

            Duration

            22 days

            Prices from

            £5,655 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.
            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
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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
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            News, Reviews & Stories

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            September 21, 2026
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            Riding along the southern spain coastline on the badlands of spain

            9 must-ride Spanish cycling routes  

            Spanish cycling routes offer some of Europe's most rewarding riding, from dramatic mountain passes and quiet coastal roads to rolling vineyards and remote pueblos blancos (white villages). Few people know these bike tours in Spain better than Dan Hirst, Head of Skedaddle España. Dan has spent more than two decades living near Tarifa, mainland Spain's ...

            Dan Hirst, Head of Skedaddle Espana
            Dan Hirst
            September 4, 2026

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