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          2027 Cycling Tours To Book Now

          We found 9 Holidays in your search for:

          Destinations (75)
          Types of Cycling / Grades (1)
          Departure Month

          2026

          2027

          2028

          Level of Support

          We found 9 Holidays in your search for:

          Select Order Order By
          Destinations (75)
          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
          Select Order Order By
          Guided
          $125 OFF
          Guided
          Italy

          Emilia-Romagna - The Food Valley

          Guided Leisure Bike Tour

          Duration

          8 days

          Prices from

          $2,980 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 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.
          24/04/2027
          $125 OFF
          01/05/2027$2,980.00
          29/05/2027
          $125 OFF
          05/06/2027$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
          Guided
          $125 OFF
          Guided
          Scotland

          Scotland - The Caledonia Way

          Guided Leisure Bike Tour

          Duration

          8 days

          Prices from

          $3,125 P.P.
          View Reviews
          5
          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.
          02/05/2027
          $125 OFF
          09/05/2027$3,125.00
          23/05/2027
          $125 OFF
          30/05/2027$3,125.00
          11/07/2027
          $125 OFF
          18/07/2027$3,125.00
          05/09/2027
          $125 OFF
          12/09/2027$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
          Guided
          Guided
          United Kingdom

          Land's End to John O'Groats Explorer

          Guided Electric Bike Tour

          Duration

          22 days

          Prices from

          $7,205 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 Tour

          E-BIKE TOUR

          This tour 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$7,205.00
          19/06/2027
          Last Spaces
          10/07/2027$7,205.00
          11/09/202702/10/2027$7,205.00
          • 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
          Guided
          Scotland

          Scotland - Hebridean Way

          Guided Leisure Bike Tour

          Duration

          7 days

          Prices from

          $3,765 P.P.
          View Reviews
          5
          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.
          23/05/202729/05/2027$3,765.00
          06/06/2027
          Guaranteed
          12/06/2027$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
          Guided
          $125 OFF
          Guided
          Spain

          Andalucia - Costa de la Luz and Ancient Cadiz

          Guided Leisure Bike Tour

          Duration

          8 days

          Prices from

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

          Andalucia - Costa de la Luz and Ancient Cadiz

          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.
          17/10/2026
          Fully Booked
          24/10/2026$3,280.00
          20/10/2026
          Last Spaces
          27/10/2026$3,280.00
          30/03/2027
          $125 OFF
          06/04/2027$3,325.00
          06/06/2027
          $125 OFF
          13/06/2027$3,325.00
          19/09/2027
          $125 OFF
          26/09/2027$3,325.00
          • 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
          Supported
          $60 OFF
          Supported
          United Kingdom

          C2C - Coast to Coast

          Supported Leisure Bike Tour

          Duration

          5 days

          Prices from

          $1,325 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 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. 

          Start DateEnd DatePrice p.p.
          21/05/2027
          Last Spaces
          25/05/2027$1,325.00
          16/07/2027
          $60 OFF
          20/07/2027$1,325.00
          06/08/2027
          $60 OFF
          10/08/2027$1,325.00
          27/08/2027
          $60 OFF
          31/08/2027$1,325.00
          24/09/2027
          $60 OFF
          28/09/2027$1,325.00
          • 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
          $150 OFF
          Guided
          Italy

          Tuscany to Rome

          Guided Electric Bike Tour

          Duration

          8 days

          Prices from

          $3,565 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.
          08/05/2027
          $150 OFF
          15/05/2027$3,565.00
          04/09/2027
          $150 OFF
          11/09/2027$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
          Self-Guided
          $95 OFF
          Self-Guided
          Sweden

          Stockholm's Archipelago

          Self-Guided Leisure Bike Tour

          Duration

          7 days

          Prices from

          $1,950 P.P.
          View Reviews
          1
          1
          2
          3
          4
          5
          Grade 3 : Moderate
          More Info BOOK NOW

          Stockholm's Archipelago

          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.

          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 $1950 16-29 May and 30-12 Sep

          Season 2 $2035 30 May – 19 Jun / 21-29 Aug

          Season 3 $2180 20 Jun – 20 Aug

          2026 16 May – 12 Sep

          Season 1 $2035 16-29 May and 30-12 Sep

          Season 2 $2135 30 May – 19 Jun / 21-29 Aug

          Season 3 $2280 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
          Guided
          France

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

          Guided Electric Bike Tour

          Duration

          23 days

          Prices from

          $9,990 P.P.
          1
          2
          3
          4
          5
          Grade 4 : Active
          More Info BOOK NOW

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

          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.
          03/05/2027
          Fully Booked
          25/05/2027$9,990.00
          27/09/2027
          Fully Booked
          19/10/2027$9,990.00
          • 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

          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
          Next

          News, Reviews & Stories

          winter cycling in costa rica - two cyclists admiring the tropical view

          7 winter cycling destinations for sun-seekers

          The best winter cycling destinations provide a wonderful way to leave winter behind and discover new roads, cultures and landscapes on two wheels. Whether you're seeking winter sunshine, aiming to build fitness with some early-season training miles, or looking for an adventure to kick-start the year, there's plenty of winter cycling destinations offering warmer, sunnier ...

          David Hall - Road Cycling Product Specialist at Saddle Skedaddle
          David Hall
          October 2, 2026
          Cycling in Andalucia

          Sierras to the Coast: The best road cycling in Andalucia 

          If you’re looking for a top European cycling destination, then road cycling in Andalucia has to be up there with the best! Plus, with beautiful weather almost year-round, it’s the ideal destination for extending your cycling season. Head of Skedaddle España, Dan, has lived in this region for more than 25 years, guiding countless cycling ...

          Dan Hirst, Head of Skedaddle Espana
          Dan Hirst
          October 1, 2026
          Cycle route in Dumfries and Galloway

          Skedaddle guide to the best cycle routes in Dumfries and Galloway

          Dave Shuttle, UK Route Developer and Guide, talks us through our cycle routes in Dumfries and Galloway and why our newest leisure cycling holiday should be on your wish list for next year.   Over the years, Dave has guided and scouted multiple cycling routes in Scotland, so who better to give us a breakdown ...

          Dave Shuttle - UK Product Lead at Saddle Skedaddle
          Dave Shuttle
          September 21, 2026

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