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          2027 Cycling Tours To Book Now

          We found 89 Holidays in your search for:

          Destinations (74)
          Types of Cycling / Grades (7)
          Departure Month

          2026

          2027

          2028

          Level of Support

          We found 89 Holidays in your search for:

          Select Order Order By
          Destinations (74)
          Types of Cycling / Grades (7)
          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
          • BOOK EARLY US

          Page 5 of 9

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

          Hadrian's Cycleway (3 days cycling)

          Self-Guided Leisure Bike Tour

          Duration

          4 days

          Prices from

          $710 P.P.
          View Reviews
          6
          1
          2
          3
          4
          5
          Grade 3 : Moderate
          More Info BOOK NOW

          Hadrian's Cycleway (3 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.

          Start DateEnd DatePrice p.p.
          24/07/2026
          Guaranteed
          27/07/2026$710.00
          07/08/202610/08/2026$710.00

          Daily departures available from April to mid October.

          Choose your own dates from:

          2026 $880 per person

          2027 $900 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 sense of achievement having ridden from coast to coast
          • The well preserved forts of Birdoswald and Vindolanda
          • The rugged beauty of the North Pennines
          • The picturesque market town of Corbridge
          • Following in the footsteps of the Roman Empire
          • Flexibility to choose your own start date or one of our great value scheduled departure dates
          Photo Highlights Dates
          Self-Guided
          Self-Guided
          United Kingdom

          Hadrian's Cycleway (4 days cycling)

          Self-Guided Leisure Bike Tour

          Duration

          5 days

          Prices from

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

          Hadrian's Cycleway (4 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.

          Start DateEnd DatePrice p.p.
          24/07/2026
          Guaranteed
          28/07/2026$850.00
          07/08/2026
          Fully Booked
          11/08/2026$850.00

          Daily departures available from April to mid October.

          Choose your own dates from:

          2026 $1040 per person

          2027 $1060 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.

          Alternatively for a great value holiday choose one of our scheduled weekend departures below.

          • The sense of achievement having ridden from coast to coast
          • The well preserved forts of Birdoswald and Vindolanda
          • The rugged beauty of the North Pennines
          • The picturesque market town of Corbridge
          • Following in the footsteps of the Roman Empire
          • Flexibility to choose your own start date or one of our great value scheduled departure dates
          Photo Highlights Dates
          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
          Last Spaces
          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
          5
          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
          Fully Booked
          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
          France

          St Malo to Nice Explorer

          Guided Road Bike Tour

          Duration

          20 days

          Prices from

          $8,420 P.P.
          View Reviews
          19
          1
          2
          3
          4
          5
          Grade 3: Moderate
          More Info BOOK NOW

          St Malo to Nice Explorer

          Guided Road Bike Tour

          Start DateEnd DatePrice p.p.
          07/09/2026
          Guaranteed
          26/09/2026$8,420.00
          25/05/202713/06/2027$8,680.00
          06/09/202725/09/2027$8,680.00
          • Cycling along the Brittany coast with views out to the Abbey of Mont St-Michel
          • 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
          Italy

          Dolomites of Brenta

          Electric Mountain Bike Tour

          Duration

          7 days

          Prices from

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

          Dolomites of Brenta

          Electric Mountain Bike Tour

          ELECTRIC MOUNTAIN BIKE TOUR

          If you love mountain biking let us show you the thrills of an e-MTB adventure. On this specially designed holiday we’ll be making the most of everything an e-MTB has to offer, with incredible climbs as well as fun descents. Hire one of our quality e-mountain bikes and experience the buzz of a pedal-assisted ride. Remember to select your e-MTB hire when you book a holiday with us.

          Start DateEnd DatePrice p.p.
          27/06/202603/07/2026$3,280.00
          29/08/202604/09/2026$3,280.00
          19/06/202725/06/2027$3,425.00
          24/07/202730/07/2027$3,425.00
          • Everchanging mountain scenery
          • Scrumptious polenta and stew at the best little refuge of the Dolomites
          • Gazing over the most famous peaks of the Dolomites
          • Rolling through alpine pastures
          • Italian gelato after a day on your bike
          • Biking through beech forests and flower filled meadows
          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
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          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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          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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