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            Small Group Cycling Holidays

            We found 104 Holidays in your search for:

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

            2025

            2026

            2027

            Level of Support

            We found 104 Holidays in your search for:

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

            2025

            2026

            2027

            Level of Support

            Join a group of likeminded riders on a small group holiday with Skedaddle! Whether you’re looking to join as a couple, group of friends, or as a solo traveller, you’ll feel part of one passionate pedallin’ community. Our tour leaders and guides will be on hand throughout your trip to ensure everything runs smoothly. You’ll also have a dedicated support vehicle to assist with everything from mechanical issues to emergency back-up and extra supplies.

            On a group tour, we take care of all your accommodation and luggage transfers. The only thing you’ll need to focus on is turning the pedals, enjoying the beautiful scenery and wondering what you’ll have for lunch (did we mention the legendary Skedaddle picnics?). It’s no wonder our small group tours are so popular!

            Read More
            • All Cycling Holidays
            • SMALL GROUP CYCLING HOLIDAYS

            Page 2 of 11

            Select Order Order By
            Guided
            Guided
            United Kingdom

            Land's End to John O'Groats Classic

            Guided Road Cycling Holiday

            Duration

            16 days

            Prices from

            £3,395 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

            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.
            24/05/2025
            Contact Us
            08/06/2025£3,395.00
            * 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
            France

            Trans Pyrenees Challenge

            Guided Road Cycling Holiday

            Duration

            10 days

            Prices from

            £3,095 P.P.
            View Reviews
            8
            1
            2
            3
            4
            5
            Grade 4 : Challenging
            More Info BOOK NOW

            Trans Pyrenees Challenge

            Guided Road Cycling Holiday

            Start DateEnd DatePrice p.p.
            03/07/2025
            Last Spaces
            12/07/2025£3,095.00
            * 21/08/202530/08/2025£3,095.00
            • Riding the entire length of Europe’s most dramatic mountain range
            • Looking down on the switchbacks ahead from the summits of the Aspin and the Port de Pailhères
            • The breath-taking descent from the top of the Tourmalet
            • Fresh crepes and a coffee at the summit of Col de Peyresourde
            • Bathing tired legs in the outdoor thermal waters in Ax-les-Thermes
            • Fine Spanish food and wine in Bossost
            • A picnic and celebratory drinks on the beach by the Med
            Photo Highlights Dates
            Guided
            Guided
            United Kingdom

            Scotland - Tour d'Ecosse

            Guided Road Cycling Holiday

            Duration

            8 days

            Prices from

            £1,765 P.P.
            View Reviews
            11
            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.
            * 17/05/2025
            Fully Booked
            24/05/2025£1,765.00
            * 14/06/2025
            Last Spaces
            21/06/2025£1,765.00
            * 28/06/2025
            Guaranteed
            05/07/2025£1,765.00
            * 19/07/2025
            Fully Booked
            26/07/2025£1,765.00
            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
            • The swooping coastal road from Ullapool to Kinlochewe
            Photo Highlights Dates
            Guided
            Guided
            Italy

            Alps and Dolomites - Giants of the Giro

            Guided Road Cycling Holiday

            Duration

            9 days

            Prices from

            £2,465 P.P.
            View Reviews
            17
            1
            2
            3
            4
            5
            Grade 4 - 5: Challenging/ Demanding
            More Info BOOK NOW

            Alps and Dolomites - Giants of the Giro

            Guided Road Cycling Holiday

            Start DateEnd DatePrice p.p.
            * 25/07/2025
            Fully Booked
            02/08/2025£2,465.00
            * 16/08/202524/08/2025£2,465.00
            24/07/202601/08/2026£2,595.00
            15/08/202623/08/2026£2,595.00
            • Cycling through the best alpine and dolomite scenery of Italy
            • Climbing the iconic Mortirolo, Passo Gavia and Passo Stelvio of Giro d’Italia fame
            • Enjoying post-ride relaxation in typical chalet-style mountain hotels
            • Re-charging your energy levels every evening with tasty local fayre
            • Testing your legs and endurance on the final Monte Grappa climb
            • Enjoying an aperitif in the lively towns of San Pellegrino Terme, Bormio and Bassano del Grappa
            Photo Highlights Dates
            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£4,495.00
            • 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
            Spain

            Sierra Nevada and Granada

            Guided Road Cycling Holiday

            Duration

            7 days

            Prices from

            £1,885 P.P.
            View Reviews
            6
            1
            2
            3
            4
            5
            Grade 3 - 4: Moderate/ Challenging
            More Info BOOK NOW

            Sierra Nevada and Granada

            Guided Road Cycling Holiday

            Start DateEnd DatePrice p.p.
            12/10/2025
            Guaranteed
            18/10/2025£1,885.00
            • Checking out the white mountain villages of the Alpujarras
            • A night in a luxurious cave house in Guadix
            • The Sierra Nevada Challenge – riding to the roof of Spain
            • The classic Vuelta ride through the Sierra de Pandera
            • Tasty tapas and sunset sangrias
            • The descent to Granada and its amazing Alhambra Palace
            Photo Highlights Dates
            Guided
            Guided
            Italy

            Lakes of Lombardia

            Guided Road Cycling Holiday

            Duration

            8 days

            Prices from

            £2,395 P.P.
            View Reviews
            20
            1
            2
            3
            4
            5
            Grade 3 : Moderate
            More Info BOOK NOW

            Lakes of Lombardia

            Guided Road Cycling Holiday

            Start DateEnd DatePrice p.p.
            * 12/07/2025
            Guaranteed
            19/07/2025£2,395.00
            * 02/08/202509/08/2025£2,395.00
            • Riding into Switzerland from Lake Maggiore to Lake Lugano
            • The ascent to Madonna del Ghisallo and the world famous cycling museum
            • Strolling through Bellagio on Lake Como after a great lake-side ride
            • Conquering Passo Maniva and the sweeping downhill to Lago di Idro
            • Relaxing with a post-ride drink overlooking yet another beautiful lake
            • Enjoying good food, fine wines and quality accommodation
            Photo Highlights Dates
            Guided
            Guided
            Italy

            Sardinia - Island Flavours

            Guided Leisure Cycling Holiday

            Duration

            8 days

            Prices from

            £1,895 P.P.
            View Reviews
            11
            1
            2
            3
            4
            5
            Grade 3 : Moderate
            More Info BOOK NOW

            Sardinia - Island Flavours

            Guided Leisure Cycling Holiday

            OPTIONAL E-BIKE DEPARTURES

            We offer this holiday with an e-bike only departure as well as regular trips where you can choose a regular bike or a pedal assist e-bike hire. Our e-bike only departures allow 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. You may choose to hire an e-bike on a regular trip but bear in mind that the pace will be set to riders without an e-bike.

            Start DateEnd DatePrice p.p.
            20/09/2025 E-Bike Departure27/09/2025£1,895.00
            11/10/2025
            Guaranteed
            18/10/2025£1,895.00
            • Checking out the UNESCO heritage site of Barumini Nuraghe
            • Enjoying the long descent to Fluminimaggiore and Masua
            • Sampling local specialties at Carloforte, on St Pietro island
            • Riding along the Nebida coastline and marvelling at the view of Pan di Zucchero
            • Experiencing the friendliness and hospitality of the Sardinian people
            • Discovering the white beaches along the south-west coastal road
            Photo Highlights Dates
            Guided
            Guided
            Italy

            Tuscany - Giro della Toscana

            Guided Road Cycling Holiday

            Duration

            8 days

            Prices from

            £2,035 P.P.
            View Reviews
            22
            1
            2
            3
            4
            5
            Grade 3 : Moderate
            More Info BOOK NOW

            Tuscany - Giro della Toscana

            Guided Road Cycling Holiday

            Start DateEnd DatePrice p.p.
            31/05/2025
            Guaranteed
            07/06/2025£2,035.00
            * 30/08/2025
            Last Spaces
            06/09/2025£2,035.00
            • Cycling through the historic wine regions of Tuscany, stopping off for a bit of wine tasting along the way
            • Staying in quality accommodation, with fantastically warm hospitality
            • Easing along the rolling hills of the Colli Sienesi
            • Riding the stunning UNESCO heritage region of Val d’Orcia
            • Stopping off at the lovely San Gimignano and Montalcino
            • Chilling out with a post-ride Chianti
            Photo Highlights Dates
            Guided
            Guided
            United Kingdom

            Land's End to John O'Groats Explorer

            Guided Road Cycling Holiday

            Duration

            22 days

            Prices from

            £4,845 P.P.
            View Reviews
            23
            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.
            10/05/2025
            Last Spaces
            31/05/2025£4,845.00
            * 07/06/2025
            Last Spaces
            28/06/2025£4,845.00
            12/07/2025
            Last Spaces
            02/08/2025£4,845.00
            * 26/07/2025
            Guaranteed
            16/08/2025£4,845.00
            06/09/2025
            Last Spaces
            27/09/2025£4,845.00
            09/05/202630/05/2026£5,095.00
            11/07/202601/08/2026£5,095.00
            05/09/202626/09/2026£5,095.00
            • 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
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            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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