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            Bestsellers - 2027 Holidays to Book Now

            We found 45 Holidays in your search for:

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

            2026

            2027

            2028

            Level of Support

            We found 45 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 2 of 5

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            Guided
            Guided
            Italy

            Grand Traverse Classic - North to South

            Guided Road Cycling Holiday

            Duration

            17 days

            Prices from

            £4,195 P.P.
            View Reviews
            9
            1
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            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.
            24/09/2026
            Last Spaces
            10/10/2026£4,195.00
            20/05/202705/06/2027£4,325.00
            23/09/202709/10/2027£4,325.00
            • 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 - Wild About Argyll

            Guided Gravel Riding Holiday

            Duration

            7 days

            Prices from

            £1,695 P.P.
            View Reviews
            6
            1
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            3
            4
            5
            Grade 3 : Moderate
            More Info BOOK NOW

            Scotland - Wild About Argyll

            Guided Gravel Riding Holiday

            Start DateEnd DatePrice p.p.
            30/08/2026
            Contact Us
            05/09/2026£1,695.00
            06/06/202712/06/2027£1,755.00
            01/08/202707/08/2027£1,755.00
            12/09/202718/09/2027£1,755.00
            • Scenic shorelines on Loch Goil, Loch Long and Loch Eck
            • Lush forest with a variety of trails and textbook gravel riding
            • Pairing Scotland’s finest seafood with local whisky and craft beer
            • Deep glens beneath towering mountains in Loch Lomond & the Trossachs National Park
            • Sunsets across Loch Fyne at Portavadie
            • Chance to spot otters, red squirrels and white-tailed eagles
            Photo Highlights Dates
            Guided
            Guided
            Spain

            Basque Country to Andalucia Classic - North to South

            Guided Road Cycling Holiday

            Duration

            16 days

            Prices from

            £3,995 P.P.
            View Reviews
            21
            1
            2
            3
            4
            5
            Grade 4 : Challenging
            More Info BOOK NOW

            Basque Country to Andalucia Classic - North to South

            Guided Road Cycling Holiday

            Start DateEnd DatePrice p.p.
            27/09/202612/10/2026£3,995.00
            11/04/202726/04/2027£4,095.00
            25/09/202710/10/2027£4,095.00
            • Cycling through the varied beauty of 14 national parks
            • Delicious regional dishes which change from day to day as you traverse the entire country
            • Crossing the granite Guadarrama and Gredos mountain ranges as you move from the north to the south of the country
            • Views over the Straits of Gibraltar to Morocco
            • The beautiful towns of San Sebastian, Guadaloupe and Ronda
            • The satisfaction of arriving in to Tarifa with over 1,000 miles of Spanish roads having passed beneath your wheels
            Photo Highlights Dates
            Guided
            Guided
            Colombia

            Emerald Mountains

            Guided Road Cycling Holiday

            Duration

            13 days

            Prices from

            £4,195 P.P.
            View Reviews
            28
            1
            2
            3
            4
            5
            Grade 4 : Challenging
            More Info BOOK NOW

            Emerald Mountains

            Guided Road Cycling Holiday

            Start DateEnd DatePrice p.p.
            16/01/2027
            Guaranteed
            28/01/2027£4,195.00
            06/02/202718/02/2027£4,195.00
            15/01/202827/01/2028£4,395.00
            05/02/202817/02/2028£4,395.00
            • Exploring unspoiled Andean highlands
            • The historic city of Cartagena
            • The hospitality of locals, so proud to show off their country
            • The challenges offered by Colombia’s dramatic mountains
            • Cycling with the warm Caribbean breeze at your back
            • Being amongst the first to ride in this emerging destination
            Photo Highlights Dates
            Guided
            Guided
            Uzbekistan

            Beyond The Silk Road

            Guided Cycling Holiday

            Duration

            14 days

            Prices from

            £4,395 P.P.
            View Reviews
            6
            1
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            3
            4
            5
            Grade 3 : Moderate
            More Info BOOK NOW

            Beyond The Silk Road

            Guided Cycling Holiday

            Start DateEnd DatePrice p.p.
            02/10/2026
            Fully Booked
            15/10/2026£4,395.00
            21/05/202703/06/2027£4,495.00
            01/10/202714/10/2027£4,495.00
            • Wandering around beautiful Bukhara and its bazaars
            • Exploring Zaamin National Park’s soaring peaks and lush pastures
            • Marvelling at Samarkand’s Mosques and Minarets
            • Riding the legendary Lake Chavac Loop
            • Spending the night in a traditional yurt, enjoying campfires and unforgettable sunsets
            • Pedalling through Sarmysh and its ancient petroglyphs
            Photo Highlights Dates
            Supported
            Supported
            United Kingdom

            C2C - Coast to Coast

            Supported Leisure Cycling Holiday

            Duration

            5 days

            Prices from

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

            C2C - Coast to Coast

            Supported 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.
            25/09/2026
            Fully Booked
            29/09/2026£895.00
            21/05/202725/05/2027£925.00
            16/07/202720/07/2027£925.00
            06/08/202710/08/2027£925.00
            27/08/202731/08/2027£925.00
            24/09/202728/09/2027£925.00
            • UK’s favourite long distance cycle route
            • Dramatic landscapes of the Lake District and Pennines
            • Cycle friendly route – cycle paths and quiet country lanes
            • Fully supported and awesome Skedaddle lunches
            • Bike friendly B&Bs offering mouthwatering breakfasts
            • Great sense of achievement, crossing the country, coast to coast
            Photo Highlights Dates
            Guided
            Guided
            Spain

            Pyrenees All Mountain Traverse

            Guided Mountain Bike Holiday

            Duration

            8 days

            Prices from

            £2,465 P.P.
            View Reviews
            10
            1
            2
            3
            4
            5
            Grade 4 : Challenging
            More Info BOOK NOW

            Pyrenees All Mountain Traverse

            Guided Mountain Bike Holiday

            OPTIONAL E-MTB DEPARTURES

            We offer this holiday with an e-MTB only departure as well as regular trips where you can choose a normal bike or a pedal assist e-MTB hire. Boost your riding off the beaten track! Our e-MTB only departures offer experienced riders the chance to enjoy a phenomenal e-mountain biking adventure with Skedaddle. Hire one of our quality e-mountain bikes and experience the buzz of a pedal-assisted ride. You may choose to hire an e-MTB on a regular tour date for this holiday but bear in mind that the pace will be set to riders without an e-bike.

            Start DateEnd DatePrice p.p.
            01/10/2026 E-Bike Departure
            Guaranteed
            08/10/2026£2,465.00
            23/05/202730/05/2027£2,525.00
            03/10/2027 E-Bike Departure10/10/2027£2,525.00
            • Oh, just sweet, sweet singletrack everywhere
            • The full traverse of the stunning Tena valley
            • Riding ancient singletrack steeped with history and heritage
            • Exploring the untouched Spanish Pyrenees
            • Enjoying tasty local cuisine with a glass of Somantano Red
            • Taking on el Classico from San Andreas hermitage
            Photo Highlights Dates
            Guided
            Guided
            Italy

            NEW! Emilia-Romagna - The Food Valley

            Guided Leisure Cycling Holiday

            Duration

            8 days

            Prices from

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

            NEW! Emilia-Romagna - The Food Valley

            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.
            29/08/2026
            Fully Booked
            05/09/2026£1,995.00
            24/04/202701/05/2027£2,085.00
            29/05/202705/06/2027£2,085.00
            18/09/202725/09/2027£2,085.00
            • Riding along quiet roads and cycle paths through beautiful countryside
            • Sampling tasty slow-food produce on the Food Valley Bike route from Cremona to Parma
            • Tasting authentic Italian food in their towns of origin such as Parma Ham, Parmigiano Reggiano, Balsamic Vinegar, and Bolognese Ragù
            • Visiting Busseto and Roncole, where the famous Italian composer Giuseppe Verdi was born
            • Exploring modern and bustling Modena
            • Taking in the vibrant university city of Bologna
            Photo Highlights Dates
            Guided
            Guided
            Scotland

            Scotland - Hebridean Way

            Guided Leisure Cycling Holiday

            Duration

            7 days

            Prices from

            £2,555 P.P.
            View Reviews
            4
            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.

            Start DateEnd DatePrice p.p.
            * 16/08/2026
            Fully Booked
            22/08/2026£2,555.00
            30/08/2026
            Fully Booked
            05/09/2026£2,555.00
            02/05/202708/05/2027£2,635.00
            23/05/202729/05/2027£2,635.00
            06/06/2027
            Guaranteed
            12/06/2027£2,635.00
            27/06/202703/07/2027£2,635.00
            08/08/202714/08/2027£2,635.00
            29/08/202704/09/2027£2,635.00
            12/09/202718/09/2027£2,635.00
            • 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
            Costa Rica

            Volcanes y Playas

            Guided Cycling Holiday

            Duration

            12 days

            Prices from

            £3,295 P.P.
            View Reviews
            16
            1
            2
            3
            4
            5
            Grade 3 : Moderate
            More Info BOOK NOW

            Volcanes y Playas

            Guided Cycling Holiday

            Start DateEnd DatePrice p.p.
            20/10/202631/10/2026£3,295.00
            22/12/202602/01/2027£3,595.00
            05/01/202716/01/2027£3,395.00
            19/10/202730/10/2027£3,395.00
            22/12/202702/01/2028£3,695.00
            • Enjoying biking through the very heart of Costa Rica
            • Taking a pre-lunch dip in the Pacific Ocean near Samara
            • Biking the rancher routes of Guanacaste
            • Searching out wildlife as you cycle along
            • Sunset on Coyote Beach with a chilled Imperial
            • Cycling across the Continental Divide
            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

            View of the Col d'Allos mountain pass in the French Alps

            Customer Story: Cycling Mont Ventoux and Alpe d’Huez

            After a long hiatus, Paul rejoined us on a Skedaddle tour in the French Alps to conquer classic climbs, including cycling Mont Ventoux. Discover his highlights of this epic road cycling trip below. If there was a prize for the longest gap between Saddle Skedaddle holidays, I might just walk away with it. In the ...

            paul streets
            Paul Streets
            August 3, 2026

            Gallovidian Gravel – a New Gravel Scotland Adventure

            Gravel riding in Scotland just got better! Gallovidian Gravel joins Cycling UK’s growing collection of long-distance must-ride routes.   Since launching our gravel holiday range in 2023, we’ve sampled some of the best gravel riding in Scotland, so we were delighted to be involved in helping Cycling UK create a new off-road route in Dumfries and Galloway - 'Galloway Gravel Escape'. Working ...

            Dave Shuttle - UK Product Lead at Saddle Skedaddle
            Dave Shuttle
            July 25, 2026
            Cyclists riding Hartside Pass on the coast to coast cycle route

            Our official guide to the UK C2C – Coast to Coast ride

              The C2C, also known as the Sea to Sea or Coast to Coast, is undoubtedly the UK’s best-loved challenge ride and attracts a vast array of enthusiastic cyclists each year to take on its legendary ups and downs. This rewarding multi-day coast to coast adventure has become somewhat of a rite of passage for us here in the ...

            Amy McKie
            Amy McKie
            July 22, 2026

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