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            Bestsellers - 2027 Holidays to Book Now

            We found 10 Holidays in your search for:

            Destinations (83)
            Types of Cycling / Grades (1)
            Departure Month

            2026

            2027

            2028

            Level of Support

            We found 10 Holidays in your search for:

            Select Order Order By
            Destinations (83)
            Types of Cycling / Grades (1)
            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
            • All Leisure Cycling Holidays
            • BOOK EARLY
            Select Order Order By
            Guided
            £100 OFF
            Guided
            Spain

            Andalucia - Costa de la Luz and Ancient Cadiz

            Guided Leisure Cycling Holiday

            Duration

            8 days

            Prices from

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

            Andalucia - Costa de la Luz and Ancient Cadiz

            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.
            17/10/2026
            Fully Booked
            24/10/2026£2,295.00
            20/10/2026
            Last Spaces
            27/10/2026£2,295.00
            30/03/2027
            £100 OFF
            06/04/2027£2,325.00
            06/06/2027
            £100 OFF
            13/06/2027£2,325.00
            19/09/2027
            £100 OFF
            26/09/2027£2,325.00
            • Exploring the endless coastal trails surrounding Tarifa
            • Indulging in delicious, freshly-caught seafood in Sanlucar
            • Savouring a glass of sherry in a historic bodega within the Sherry Triangle
            • Immersing ourselves in true Andalucian culture and enjoying some Flamenco
            • Riding along the peaceful, traffic-free EuroVelo routes
            • Experiencing the lively, vibrant town of Tarifa, the gateway to two continents
            Photo Highlights Dates
            Guided
            Guided
            France

            NEW! France - St Malo to Nice Explorer (23 Days)

            Guided Electric Bike Holiday

            Duration

            23 days

            Prices from

            £6,995 P.P.
            1
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            3
            4
            5
            Grade 4: Active
            More Info BOOK NOW

            NEW! France - St Malo to Nice Explorer (23 Days)

            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.
            03/05/2027
            Fully Booked
            25/05/2027£6,995.00
            27/09/2027
            Fully Booked
            19/10/2027£6,995.00
            • Cycling almost 1000 pedal-assisted miles through 19 of France’s regional départements
            • Cruising along the Brittany coast, admiring the dramatic landscapes and picturesque shoreline
            • Cycling in the Loire Valley, admiring the many châteaux and sampling the region’s famous wines
            • Meandering along the Loire, Dordogne, Lot and Rhône rivers
            • Rolling through the vineyards of Châteauneuf-du-Pape
            • Enjoying the changing French flavours, from the dairy-rich north to the Mediterranean south
            • Marvelling at the spectacular Gorges de l’Ardèche, Gorge de la Nesque and Gorges du Verdon
            • Celebrating the achievement of conquering the St Malo to Nice cycle route with a glass of fizz on the French Riviera
            Photo Highlights Dates
            Self-Guided
            £75 OFF
            Self-Guided
            Sweden

            Stockholm's Archipelago

            Self-Guided Leisure Cycling Holiday

            Duration

            7 days

            Prices from

            £1,365 P.P.
            View Reviews
            1
            1
            2
            3
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            5
            Grade 3 : Moderate
            More Info BOOK NOW

            Stockholm's Archipelago

            Self-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.

            The season prices below are per person. Daily departures are available between and inclusive of the stated dates.

            2026 16 May – 12 Sep

            Season 1 £1365 16-29 May and 30 Aug – 12 Sep

            Season 2 £1425 30 May – 19 Jun / 21-29 Aug

            Season 3 £1525 20 Jun – 20 Aug

            2027 16 May – 12 Sep

            Season 1 £1425 16-29 May and 30 Aug – 12 Sep

            Season 2 £1495 30 May – 19 Jun / 21-29 Aug

            Season 3 £1595 20 Jun – 20 Aug

            • Exploring scenic Stockholm
            • Island hopping by ferry and bike through coastal Sweden
            • Riding forest trails and waterside routes
            • Exploring harbour towns like Vaxholm and Gustavsberg
            • Discovering Sandhamn’s beaches, boats and colourful charm
            • Stopping for fika, lunches and sea views along the way
            • Soaking up the archipelago’s unique mix of nature and culture
            Photo Highlights Dates
            Guided
            £100 OFF
            Guided
            Scotland

            Scotland - The Caledonia Way

            Guided Leisure Cycling Holiday

            Duration

            8 days

            Prices from

            £2,185 P.P.
            View Reviews
            5
            1
            2
            3
            4
            5
            Grade 4: Active
            More Info BOOK NOW

            Scotland - The Caledonia 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.
            02/05/2027
            £100 OFF
            09/05/2027£2,185.00
            23/05/2027
            £100 OFF
            30/05/2027£2,185.00
            11/07/2027
            £100 OFF
            18/07/2027£2,185.00
            05/09/2027
            £100 OFF
            12/09/2027£2,185.00
            • Marvelling at the beauty of Kilmartin Glen and its ancient monuments
            • Enjoying traffic-free Caledonia Way cycleways and lovely canal side routes
            • Checking out Ben Nevis and The Grampians from Loch Linhe
            • Fort Augustus and taking on the legendary ascent of Glendoe
            • Exploring Knapdale – One of Scotland’s National Scenic Areas
            • Cycling to Scotland’s best-loved towns including Fort William and Fort Augustus
            Photo Highlights Dates
            Supported
            £50 OFF
            Supported
            United Kingdom

            C2C - Coast to Coast

            Supported Leisure Cycling Holiday

            Duration

            5 days

            Prices from

            £925 P.P.
            View Reviews
            2
            1
            2
            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.
            21/05/2027
            Last Spaces
            25/05/2027£925.00
            16/07/2027
            £50 OFF
            20/07/2027£925.00
            06/08/2027
            £50 OFF
            10/08/2027£925.00
            27/08/2027
            £50 OFF
            31/08/2027£925.00
            24/09/2027
            £50 OFF
            28/09/2027£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
            £100 OFF
            Guided
            Italy

            Emilia-Romagna - The Food Valley

            Guided Leisure Cycling Holiday

            Duration

            8 days

            Prices from

            £2,085 P.P.
            View Reviews
            2
            1
            2
            3
            4
            5
            Grade 2-3: Gentle/Moderate
            More Info BOOK NOW

            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.
            24/04/2027
            £100 OFF
            01/05/2027£2,085.00
            29/05/2027
            £100 OFF
            05/06/2027£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

            £2,635 P.P.
            View Reviews
            5
            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.
            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
            £125 OFF
            Guided
            Italy

            Tuscany to Rome

            Guided Electric Bike Holiday

            Duration

            8 days

            Prices from

            £2,495 P.P.
            View Reviews
            7
            1
            2
            3
            4
            5
            Grade 3 : Moderate
            More Info BOOK NOW

            Tuscany to Rome

            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.
            08/05/2027
            £125 OFF
            15/05/2027£2,495.00
            04/09/2027
            £125 OFF
            11/09/2027£2,495.00
            • Staying in Tuscan accommodation overlooking stunning landscapes
            • Discovering the amazing towns of Siena, San Quirico and Pienza
            • Sampling the best wines of Chianti, Montepulciano and Montalcino
            • Enjoying the journey from Tuscany to Rome on a variety of terrain, including ancient Roman roads
            • Exploring the lesser-known historical towns of Lazio, such as Sutri with it’s Roman amphitheatre
            • The sense of achievement riding into St Peter’s Square in Rome
            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
            £75 OFF
            Guided
            Scotland

            Scotland - Lochs and Glens

            Guided Leisure Cycling Holiday

            Duration

            7 days

            Prices from

            £1,655 P.P.
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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.
            09/05/2027
            £75 OFF
            15/05/2027£1,655.00
            13/06/2027
            £75 OFF
            19/06/2027£1,655.00
            15/08/2027
            £75 OFF
            21/08/2027£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

            Not sure which trip's right for you? Just ask!

            Get in touch and we'll help you find your perfect trip.

            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
            The guides and other group members really made the holiday enjoyable. Our guide was friendly, professional and knowledgeable.
            Elaine, Italy - Tuscany to Rome
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            All the services we received were first class. This was a real holiday and going with Skedaddle took all the stress of booking accommodation from home, route planning and so on, so all we had to do was enjoy the cycling. This has been one of the best holidays in my life.
            Alison, Italy - Sardinia Island Flavours
            Quote
            What do you like most about Skedaddle? Where do I start? The booking process, the hotels, the guides, the lunches, the places they go, the people I meet, the pit stops, the Skedaddle community, reliability, I can put my trust in them to provide a great and memorable experience.
            David, Austria & Italy - La Via Claudia
            Quote
            Skedaddle holidays are always great; you can ride your bike and they pretty much do the rest! Being able to use two wheels as a mode of transport to travel across the country, supported by Skedaddle, just shows the beauty, and power, of bikes. Thank you for making it possible!
            Kate, UK - C2C
            Quote
            We just LOVED the whole thing – route, weather, food, scenery, being outside – it was probably one of the best holidays we have had.
            Inese, Austria - The Danube Cyclepath
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