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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 3 of 3

          Select Order Order By
          Guided
          Guided
          Scotland

          Scotland - The Caledonia Way

          Guided Leisure Bike Tour

          Duration

          8 days

          Prices from

          $2,995 P.P.
          View Reviews
          6
          1
          2
          3
          4
          5
          Grade 4 : Active
          More Info BOOK NOW

          Scotland - The Caledonia 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.
          28/06/2026
          Last Spaces
          05/07/2026$2,995.00
          26/07/2026
          Contact Us
          02/08/2026$2,995.00
          06/09/2026
          Last Spaces
          13/09/2026$2,995.00
          02/05/202709/05/2027$3,125.00
          23/05/202730/05/2027$3,125.00
          11/07/202718/07/2027$3,125.00
          05/09/202712/09/2027$3,125.00
          • 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
          Self-Guided
          Self-Guided
          United Kingdom

          Cotswolds to Windsor

          Self-Guided Leisure Cycling Tour

          Duration

          5 days

          Prices from

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

          Cotswolds to Windsor

          Self-Guided Leisure Cycling Tour

          E-BIKE HIRE AVAILABLE

          This holiday is well-suited to both regular bikes and pedal assist e-bikes, and you can choose to hire either when you book your holiday 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 $1565 per person.

          2027 $1600 per person.

          For a group of 4 or more we can offer the reduced rate of 2026 $1350 / 2027 $1380.

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

          • Tracing the River Thames from near its source all the way to Windsor
          • Didcot and its impressive railway heritage
          • The impressive Uffington White Horse & Dragon Hill
          • Beautiful wooded hills and green landscapes of the Chilterns
          • World famous Windsor Castle
          • Traditional pubs and award-winning English wines at the home of the Royal Regatta
          Photo Highlights Dates
          Self-Guided
          Self-Guided
          United Kingdom

          Cotswolds Explorer

          Self-Guided Leisure Cycling Tour

          Duration

          8 days

          Prices from

          $1,995 P.P.
          View Reviews
          2
          1
          2
          3
          4
          5
          Grade 2-3: Gentle/ Moderate
          More Info BOOK NOW

          Cotswolds Explorer

          Self-Guided Leisure Cycling Tour

          Daily departures available from April to mid October.

          Choose your own dates from:

          2026 $1995 per person

          2027 $2035 per person

          For a group of 4 or more we can offer the reduced rate of 2026 $1850 / 2027 $1895

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

          • The famous Cotswolds market towns of Moreton-in-Marsh and Stow-on-the-Wold
          • Riverside relaxation in Bourton-on-the-Water, the “Venice of the Cotswolds”
          • Leisurely riding through beautiful rolling countryside
          • The historic village of Bibury, famous for its beautiful stone cottages
          • Cycling through charming chocolate box villages
          • Stately home of Blenheim Palace with 2000 acres of gardens and magnificent architecture
          Photo Highlights Dates
          Self-Guided
          Self-Guided
          Scotland

          Scotland - The Caledonia Way - Oban to Inverness

          Self-Guided Leisure Bike Tour

          Duration

          7 days

          Prices from

          $1,710 P.P.
          View Reviews
          1
          1
          2
          3
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          5
          Grade 3-4 : Moderate/Active
          More Info BOOK NOW

          Scotland - The Caledonia Way - Oban to Inverness

          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.
          15/08/2026
          Fully Booked
          21/08/2026$1,710.00
          05/09/2026
          Fully Booked
          11/09/2026$1,710.00

          Daily departures (excluding Thursdays) available from April to mid October.

          Choose your own dates from:

          2026 $2135 per person

          2027 $2180 per person

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

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

          • Checking out Ben Nevis and The Grampians from Loch Linhe
          • Taking on the legendary ascent of Glendoe
          • Exploring Loch Ness and some of Scotland’s more remote National Scenic Areas, including the Appin Peninsula
          • Cycling Coast to Coast through Scotland’s best-loved towns including Oban, Fort William and Fort Augustus
          • Scenic ferry rides to the Ardgour peninsula
          • A chance to sample local whiskies at the Oban and Fort William distilleries
          Photo Highlights Dates
          Self-Guided
          Self-Guided
          United Kingdom

          NEW! UK - North York Moors, Coast and Abbeys - 5 Days Cycling

          Self-Guided Leisure Bike Tour

          Duration

          7 days

          Prices from

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

          NEW! UK - North York Moors, Coast and Abbeys - 5 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 $1565 per person

          2026 $1610 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.

          Please note that Scarborough and Whitby can be particularly busy in July and August, and hotels are less likely to have availability, so booking early is advised.

          • Scenic riding along the ‘The Cinder Track’ disused railway, with coastal views of Robin Hood’s Bay, Scarborough and Whitby
          • Riding up steep climbs and down exhilarating descents through beautiful heather moorlands on quiet roads in the North York Moors National Park
          • Tucking in to award-winning local fish & chips in Whitby harbour at the end of a long day in the saddle
          • Staying in the quaint historical Yorkshire towns and villages of Helmsley, Pickering and Great Ayton
          • The chance to visit an abundance of historic attractions including Whitby Abbey, Scarborough Castle and Rievaulx Abbey
          • Riding the serene forest tracks in Dalby Forest
          Photo Highlights Dates
          Guided
          Guided
          Italy

          NEW! Emilia-Romagna - The Food Valley

          Guided Leisure Bike Tour

          Duration

          8 days

          Prices from

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

          NEW! Emilia-Romagna - The Food Valley

          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.
          29/08/2026
          Fully Booked
          05/09/2026$2,850.00
          24/04/202701/05/2027$2,980.00
          29/05/202705/06/2027$2,980.00
          18/09/202725/09/2027$2,980.00
          • 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
          Self-Guided
          Self-Guided
          United Kingdom

          NEW! Northumberland Coast - Alnwick to Berwick

          Self-Guided Leisure Bike Tour

          Duration

          5 days

          Prices from

          $1,140 P.P.
          View Reviews
          8
          1
          2
          3
          4
          5
          Grade 1-2 : Easy/Gentle
          More Info BOOK NOW

          NEW! Northumberland Coast - Alnwick to Berwick

          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. 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. 

          Daily departures available from April to the end of September.

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

          2026 $1140 per person

          2027 $1165 per person

          Kid’s Discounts

          For children below the age of 18 who are travelling with 2 full-paying passengers, we are able to offer a 20% discount off the basic holiday cost.

          If you‘re happy sharing a family room, once we’ve received your booking we will check what rooms are available and we may be able to offer (up to) an additional 20% discount for the children (subject to availability).

          • Discovering beautiful Alnwick and its famous castle and gardens
          • Cycling over the causeway to Holy Island to check out Lindisfarne castle and priory
          • Sampling tasty fish and chips at Seahouses
          • Admiring the gorgeous sandy beaches and sweeping sand dunes of the Northumberland Coast
          • Beholding the majestic castles of Warkworth, Dustanburgh, Bamburgh and Alnwick
          • Checking out the town walls of Berwick-upon-Tweed, England’s most northern town
          Photo Highlights Dates
          • Previous page
          • 1
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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
          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
          Quote
          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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