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          2027 Cycling Tours To Book Now

          We found 27 Holidays in your search for:

          Destinations (74)
          Types of Cycling / Grades (1)
          Departure Month

          2026

          2027

          2028

          Level of Support

          We found 27 Holidays in your search for:

          Select Order Order By
          Destinations (74)
          Types of Cycling / Grades (1)
          Departure Month

          2026

          2027

          2028

          Level of Support
          2027 Road Cycling Tours 2027 Adventure Cycling Tours

          Planning ahead for your dream cycling tour? Whether you're training to complete the UK's ultimate challenge ride - Land's End to John o' Groats - or searching for your trip of a lifetime exploring a far-flung destination, we know it’s helpful to plan ahead. These tours all have 2027 dates available to book now. Plus, you’ll only need to pay a deposit upfront to secure your space.

          What are you waiting for? Stop dreaming and start planning!

          • All Cycling Holidays
          • All Leisure Cycling Tours
          • BOOK EARLY US

          Page 2 of 3

          Select Order Order By
          Self-Guided
          Self-Guided
          United Kingdom

          Hadrian's Cycleway (6 days cycling)

          Self-Guided Leisure Bike Tour

          Duration

          7 days

          Prices from

          $1,280 P.P.
          View Reviews
          6
          1
          2
          3
          4
          5
          Grade 1-2 : Easy/Gentle
          More Info BOOK NOW

          Hadrian's Cycleway (6 days cycling)

          Self-Guided Leisure Bike Tour

          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.

          Daily departures available from April to mid October.

          Choose your own dates from:

          2026 $1280 per person

          2027 $1310 per person

          You either can make a booking online or over the phone. Once we have your details, we’ll be able to check availability.

          • The well preserved forts of Birdoswald and Vindolanda
          • The rugged beauty of the North Pennines
          • The view down the Tyne as you arrive in to Newcastle
          • The picturesque market town of Corbridge
          • The sense of achievement having ridden from coast to coast
          • Following in the footsteps of the Roman Empire
          Photo Highlights Dates
          Self-Guided
          Self-Guided
          United Kingdom

          Yorkshire Wolds

          Self-Guided Leisure Bike Tour

          Duration

          6 days

          Prices from

          $1,280 P.P.
          View Reviews
          12
          1
          2
          3
          4
          5
          Grade 2-3: Gentle/ Moderate
          More Info BOOK NOW

          Yorkshire Wolds

          Self-Guided Leisure Bike Tour

          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.

          Daily departures available from April to mid October.

          Choose your own dates from:

          2026 $1280 per person

          2027 $1310 per person

          You can either make a booking online or over the phone. Once we have your details, we’ll be able to check availability.

          • Gently undulating hills with picture postcard villages
          • Medieval market towns of Pocklington, Driffield and Beverley
          • The stunning gothic Minster in Beverley
          • The manor houses of Sledmere, Sewerby and Burton Agnes
          • The cliffs and thousands of seabirds at Bempton
          • Flamborough Head Heritage Coast
          Photo Highlights Dates
          Self-Guided
          Self-Guided
          Scotland

          Scotland - Lochs and Glens

          Self-Guided Leisure Bike Tour

          Duration

          5 days

          Prices from

          $1,025 P.P.
          View Reviews
          6
          1
          2
          3
          4
          5
          Grade 3 : Moderate
          More Info BOOK NOW

          Scotland - Lochs and Glens

          Self-Guided Leisure Bike Tour

          SAVE ON 2026 ESCAPES

          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.

          Daily departures available from April to mid October.

          Choose your own dates from:

          2026 $1025 per person

          2026 $1045 per person

          Please note, due to some events happening in Killin in early-June, availability is very limited. Please chat to us if you’re looking to travel around this time and we’ll do our best to accommodate you.

          You either can make a booking online or over the phone. Once we have your details, we’ll be able to check availability.

          • Watching the sun burn away the mists from Loch Lomond
          • The beautiful lochs of Venachar, Lubnaig and Tay.
          • Enjoying a dram at one of Scotland’s whisky distilleries
          • Perth’s Georgian buildings
          • Miles of quiet winding loch-side roads
          • The spectacular mountain backdrop
          Photo Highlights Dates
          Guided
          Guided
          Austria and Italy

          La Via Claudia

          Guided Leisure Bike Tour

          Duration

          8 days

          Prices from

          $3,565 P.P.
          View Reviews
          26
          1
          2
          3
          4
          5
          Grade 3-4 : Moderate/Active
          More Info BOOK NOW

          La Via Claudia

          Guided Leisure Bike Tour

          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.
          20/06/2026
          Guaranteed
          27/06/2026$3,565.00
          18/07/2026
          Fully Booked
          25/07/2026$3,565.00
          22/08/2026
          Guaranteed
          29/08/2026$3,565.00
          19/06/202726/06/2027$3,710.00
          03/07/202710/07/2027$3,710.00
          21/08/202728/08/2027$3,710.00
          • Waking up to beautiful views of the Zugspitze, Germany’s highest peak
          • Cycling beside the vivid blue waters of the River Inn
          • Absorbing the history of an ancient trade route by bike
          • Exploring Merano – The Jewel of South Tyrol
          • Winding your way through the lovely Vinschgau Valley
          • A post-ride, tasty gelato on the shores of Lake Garda
          Photo Highlights Dates
          Guided
          Guided
          Italy

          Tuscany to Rome

          Guided Electric Bike Tour

          Duration

          8 days

          Prices from

          $3,425 P.P.
          View Reviews
          7
          1
          2
          3
          4
          5
          Grade 3 : Moderate
          More Info BOOK NOW

          Tuscany to Rome

          Guided Electric Bike Tour

          E-BIKE TOUR

          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.
          12/09/2026
          Guaranteed
          19/09/2026$3,425.00
          08/05/202715/05/2027$3,565.00
          04/09/202711/09/2027$3,565.00
          • 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
          Italy

          Sardinia - Island Flavours

          Guided Leisure Bike Tour

          Duration

          8 days

          Prices from

          $2,850 P.P.
          View Reviews
          4
          1
          2
          3
          4
          5
          Grade 3 : Moderate
          More Info BOOK NOW

          Sardinia - Island Flavours

          Guided Leisure Bike Tour

          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.
          12/09/2026
          Last Spaces
          19/09/2026$2,850.00
          10/10/2026
          Guaranteed
          17/10/2026$2,850.00
          17/04/202724/04/2027$2,995.00
          01/05/202708/05/2027$2,995.00
          11/09/202718/09/2027$2,995.00
          09/10/202716/10/2027$2,995.00
          • 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
          Scotland

          Scotland - Lochs and Glens

          Guided Leisure Bike Tour

          Duration

          7 days

          Prices from

          $2,280 P.P.
          View Reviews
          8
          1
          2
          3
          4
          5
          Grade 3-4 : Moderate/Active
          More Info BOOK NOW

          Scotland - Lochs and Glens

          Guided Leisure Bike Tour

          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.
          19/07/2026
          Fully Booked
          25/07/2026$2,280.00
          23/08/2026
          Guaranteed
          29/08/2026$2,280.00
          09/05/202715/05/2027$2,365.00
          13/06/202719/06/2027$2,365.00
          15/08/202721/08/2027$2,365.00
          • 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
          Self-Guided
          Self-Guided
          United Kingdom

          Lake District Discoverer

          Self-Guided Leisure Bike Tour

          Duration

          7 days

          Prices from

          $1,280 P.P.
          1
          2
          3
          4
          5
          Grade 2-3: Gentle/ Moderate
          More Info BOOK NOW

          Lake District Discoverer

          Self-Guided Leisure Bike Tour

          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.

          Daily departures available from April to mid October.

          Choose your own dates from:

          2026 $1280 per person

          2026 $1310 per person

          You either can make a booking online or over the phone. Once we have your details, we’ll be able to check availability.

          • Taking in a lake view over a traditional pub lunch
          • Admiring scenic villages spread across the hillsides
          • Cycling up to Castlerigg Stone Circle
          • Riding through the rugged beauty of the Langdale Valley
          • Sampling Grasmere’s famous Gingerbread
          • Glimpses of Ospreys over Dodd Wood
          Photo Highlights Dates
          Self-Guided
          Self-Guided
          Austria

          Salzburg's Lake District

          Self-Guided Leisure Bike Tour

          Duration

          8 days

          Prices from

          $1,665 P.P.
          View Reviews
          1
          1
          2
          3
          4
          5
          Grade 2 : Gentle
          More Info BOOK NOW

          Salzburg's Lake District

          Self-Guided Leisure Bike Tour

          E-BIKE HIRE AVAILABLE

          This tour is well-suited to both normal 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.

          Daily departures available. The seasonal prices below are per person, and are applicable for all start dates between and inclusive of the stated dates.

          2026 04 Apr – 04 Oct

          Season 1 – $1665 04 Apr – 17 Apr / 26 Sep – 04 Oct

          Season 2 – $1810 18 Apr – 08 May / 12 Sep – 25 Sep

          Season 3 – $1895 09 May – 11 Sep

          2027 04 Apr – 03 Oct

          Season 1 – $1750 04 Apr – 17 Apr / 26 Sep – 03 Oct

          Season 2 – $1895 18 Apr – 08 May / 12 Sep – 25 Sep

          Season 3 – $1995 09 May – 11 Sep

          • Staying in beautiful Salzburg – the City of Mozart
          • Cycling along the River Salzach and through numerous nature reserves
          • Blue skies set against snowcapped peaks shimmering in the lake waters
          • Cycling on traffic-free and well maintained cycle paths
          • Taking a refreshing lake swim after a day in the saddle
          • Enjoying a game of miniature golf in Franking
          • Visiting the monastery at Mondsee, where the wedding scene in the Sound of Music was filmed
          Photo Highlights Dates
          Guided
          Guided
          Scotland

          Scotland - Hebridean Way

          Guided Leisure Bike Tour

          Duration

          7 days

          Prices from

          $3,650 P.P.
          View Reviews
          10
          1
          2
          3
          4
          5
          Grade 3-4 : Moderate/Active
          More Info BOOK NOW

          Scotland - Hebridean Way

          Guided Leisure Bike Tour

          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.
          21/06/2026
          Fully Booked
          27/06/2026$3,650.00
          05/07/2026
          Fully Booked
          11/07/2026$3,650.00
          26/07/2026
          Fully Booked
          01/08/2026$3,650.00
          * 16/08/2026
          Guaranteed
          22/08/2026$3,650.00
          30/08/2026
          Fully Booked
          05/09/2026$3,650.00
          02/05/202708/05/2027$3,765.00
          23/05/202729/05/2027$3,765.00
          06/06/202712/06/2027$3,765.00
          27/06/202703/07/2027$3,765.00
          08/08/202714/08/2027$3,765.00
          29/08/202704/09/2027$3,765.00
          12/09/202718/09/2027$3,765.00
          • 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
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          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
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          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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