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          Winter Sun and Cycling

          We found 11 Holidays in your search for:

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

          2026

          2027

          2028

          Level of Support

          We found 11 Holidays in your search for:

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

          2026

          2027

          2028

          Level of Support

          Experience the joy of winter cycling with our inspiring range of winter cycling tours, perfect for riders looking to escape the colder months. Whether you’re trading winter weather for warmer destinations or planning a memorable way to celebrate the holiday season, our expertly crafted winter bike tours offer beautiful scenery, expert support, and an exceptional experience on the bike!

          Choose from extraordinary adventures that immerse you in fascinating cultures in Central America, South America, Africa, and Asia. Or discover winter cycling destinations in Europe where late-season sunshine and quieter roads await.

          Whether you’re searching for cycling tours in December, a rewarding way to celebrate Christmas and New Year, or planning cycling tours in January to kick-start your season, look no further - your perfect winter ride starts here!

          Want to ride at a different time of year? Don't miss our fall cycling tours and spring cycling tours.

          • All Cycling Holidays
          • WINTER CYCLING TOURS

          Page 1 of 2

          Select Order Order By
          Guided
          Guided
          Spain

          Andalucia - Los Pueblos Blancos

          Guided Road Bike Tour

          Duration

          8 days

          Prices from

          $3,135 P.P.
          View Reviews
          5
          1
          2
          3
          4
          5
          Grade 2 - 3: Gentle/Moderate
          More Info BOOK NOW

          Andalucia - Los Pueblos Blancos

          Guided Road Bike Tour

          Start DateEnd DatePrice p.p.
          25/10/2026
          Contact Us
          01/11/2026$3,135.00
          28/12/202604/01/2027$3,565.00
          • Riding the beautiful Serrania de Ronda, past white villages, chestnut groves and craggy sierras
          • A fantastic mixture of great small rural hotels
          • Exploring beautiful Ronda, perched on its magnificent gorge
          • Reaching the dramatic Puerto de las Palomas
          • Grazalema, nestled below atmospheric, limestone mountains
          • Sipping local sherries with tasty tapas in the local bodegas
          Photo Highlights Dates
          Guided
          Guided
          Costa Rica

          Ruta de los Volcanes

          Guided Road Bike Tour

          Duration

          13 days

          Prices from

          $6,280 P.P.
          View Reviews
          13
          1
          2
          3
          4
          5
          Grade 3: Moderate
          More Info BOOK NOW

          Ruta de los Volcanes

          Guided Road Bike Tour

          Start DateEnd DatePrice p.p.
          22/12/202603/01/2027$6,280.00
          13/03/202725/03/2027$6,320.00
          22/12/202703/01/2028$6,465.00
          • Spotting an unparalleled diversity of wildlife
          • Cycling in the shadow of palm trees along the Pacific coast
          • Breaking through the clouds as we cross Costa Rica’s central mountains
          • Enjoying volcanic vistas over a drink in La Fortuna
          • Watching the sun go down from Samara beach after a rewarding day in the saddle
          • The change in scenery on opposing sides of the continental divide
          Photo Highlights Dates
          Guided
          Guided
          Morocco

          Road Atlas

          Guided Road Bike Tour

          Duration

          10 days

          Prices from

          $2,710 P.P.
          View Reviews
          30
          1
          2
          3
          4
          5
          Grade 3: Moderate
          More Info BOOK NOW

          Road Atlas

          Guided Road Bike Tour

          Start DateEnd DatePrice p.p.
          07/11/2026
          Fully Booked
          16/11/2026$2,710.00
          27/12/202605/01/2027$2,710.00
          30/01/202708/02/2027$2,850.00
          06/11/202715/11/2027$2,850.00
          27/12/202705/01/2028$2,850.00
          • The High Atlas mountain range
          • The outstanding Ounila Valley and Ait Benhaddou Kasbah
          • Exploring the surreal blue rocks of Tafraoute
          • The incredible 100km ride from Tafraoute towards the coast
          • Enjoying a cold beer on one of Morocco’s finest terraces at Immouzer
          • The sights, smells and sounds of the Marrakech souk
          • Starting and finishing in this years ‘Capital of Culture’ Marrakech
          Photo Highlights Dates
          Guided
          Guided
          Chile and Argentina

          Lake District

          Guided Bike Tour

          Duration

          13 days

          Prices from

          $6,020 P.P.
          View Reviews
          45
          1
          2
          3
          4
          5
          Grade 3 : Moderate
          More Info BOOK NOW

          Lake District

          Guided Bike Tour

          Start DateEnd DatePrice p.p.
          11/10/202623/10/2026$6,020.00
          06/12/202618/12/2026$6,020.00
          10/01/202722/01/2027$6,020.00
          • Majestic Volcan Osorno and its snow-capped peak
          • Tasting the chocolates of Bariloche
          • Biking the Seven Lakes Route to San Martin de los Andes
          • The monkey-puzzle tree forests of Conguillio
          • Sampling a tasty Malbec or Carmanere after a day’s biking
          • Hiking the lofty heights of Volcan Villarica
          Photo Highlights Dates
          Guided
          Guided
          India

          Classic Kerala

          Guided Bike Tour

          Duration

          14 days

          Prices from

          $3,450 P.P.
          View Reviews
          1
          1
          2
          3
          4
          5
          Grade 3 : Moderate
          More Info BOOK NOW

          Classic Kerala

          Guided Bike Tour

          Start DateEnd DatePrice p.p.
          21/11/2026
          Guaranteed
          04/12/2026$3,450.00
          31/01/2027
          Fully Booked
          13/02/2027$3,450.00
          30/10/202712/11/2027$3,565.00
          30/01/202812/02/2028$3,620.00
          29/10/202811/11/2028$3,750.00
          • Cycling through lush tea and spice plantations
          • Periyar wildlife reserve, home to elephants, bison and tigers
          • Climbing through cool air and pristine forests
          • Drifting on a rice barge through Kerala’s backwaters
          • Relaxing on white sands of Marari Beach
          • Enjoying the best of Southern Indian Cuisine
          Photo Highlights Dates
          Guided
          Guided
          Sri Lanka

          Backroads and Beaches

          Guided Bike Tour

          Duration

          15 days

          Prices from

          $4,135 P.P.
          View Reviews
          3
          1
          2
          3
          4
          5
          Grade 3 : Moderate
          More Info BOOK NOW

          Backroads and Beaches

          Guided Bike Tour

          Start DateEnd DatePrice p.p.
          07/11/2026
          Last Spaces
          21/11/2026$4,135.00
          09/01/2027
          Last Spaces
          23/01/2027$4,135.00
          13/02/2027
          Fully Booked
          27/02/2027$4,135.00
          14/03/202728/03/2027$4,135.00
          06/11/202720/11/2027$4,135.00
          12/02/202826/02/2028$4,135.00
          04/11/202818/11/2028$4,135.00
          • Eyeing up the elephants at Udawalawe
          • Stunning Sigirya and the Lion Rock
          • Colonial cool in Nuwara Eliya
          • Coastal cycling and beautiful beaches
          • Honing in on Horton Plains after a day in the hills
          • The Knuckles and Kandy’s Temple of the Tooth
          Photo Highlights Dates
          Guided
          Guided
          Vietnam

          Mountains and Coast

          Guided Bike Tour

          Duration

          15 days

          Prices from

          $2,995 P.P.
          View Reviews
          26
          1
          2
          3
          4
          5
          Grade 3 : Moderate
          More Info BOOK NOW

          Mountains and Coast

          Guided Bike Tour

          Start DateEnd DatePrice p.p.
          14/11/202628/11/2026$3,095.00
          14/02/202728/02/2027$2,995.00
          06/03/202720/03/2027$2,995.00
          13/11/202727/11/2027$2,995.00
          12/02/202826/02/2028$2,995.00
          04/03/202818/03/2028$2,995.00
          11/11/202825/11/2028$2,995.00
          • Exploring the lesser visited parts of Vietnam by bike
          • Stunning Saigon – the ‘Pearl of the Orient’
          • Heading off the tourist trail in the Central Highlands
          • Treating your tastebuds to Vietnam’s legendary cuisine
          • Get your caffeine hit with a fresh roadside brew
          • Soaking up the sunshine at beautiful Nha Trang
          Photo Highlights Dates
          Guided
          Guided
          Colombia

          Emerald Mountains

          Guided Road Bike Tour

          Duration

          13 days

          Prices from

          $5,995 P.P.
          View Reviews
          27
          1
          2
          3
          4
          5
          Grade 4: Challenging
          More Info BOOK NOW

          Emerald Mountains

          Guided Road Bike Tour

          Start DateEnd DatePrice p.p.
          16/01/2027
          Guaranteed
          28/01/2027$5,995.00
          06/02/202718/02/2027$5,995.00
          15/01/202827/01/2028$6,280.00
          05/02/202817/02/2028$6,280.00
          • Exploring unspoiled Andean highlands
          • The historic city of Cartagena
          • The hospitality of locals, so proud to show off their country
          • The challenges offered by Colombia’s dramatic mountains
          • Cycling with the warm Caribbean breeze at your back
          • Being amongst the first to ride in this emerging destination
          Photo Highlights Dates
          Guided
          Guided
          Costa Rica

          Volcanes y Playas

          Guided Bike Tour

          Duration

          12 days

          Prices from

          $4,710 P.P.
          View Reviews
          15
          1
          2
          3
          4
          5
          Grade 3 : Moderate
          More Info BOOK NOW

          Volcanes y Playas

          Guided Bike Tour

          Start DateEnd DatePrice p.p.
          20/10/2026
          Contact Us
          31/10/2026$4,710.00
          22/12/202602/01/2027$5,135.00
          05/01/2027
          Guaranteed
          16/01/2027$4,850.00
          19/10/202730/10/2027$4,850.00
          22/12/202702/01/2028$5,280.00
          • Enjoying biking through the very heart of Costa Rica
          • Taking a pre-lunch dip in the Pacific Ocean near Samara
          • Biking the rancher routes of Guanacaste
          • Searching out wildlife as you cycle along
          • Sunset on Coyote Beach with a chilled Imperial
          • Cycling across the Continental Divide
          Photo Highlights Dates
          Self-Guided
          Self-Guided
          Portugal

          Azure Ocean Ride

          Self-Guided Leisure Bike Tour

          Duration

          8 days

          Prices from

          $2,610 P.P.
          View Reviews
          1
          1
          2
          3
          4
          5
          Grade 3 : Moderate
          More Info BOOK NOW

          Azure Ocean Ride

          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. The season prices below are per person and are applicable for all start dates between and inclusive of the stated dates.

          2026 05 Jan – 13 Dec (excl. Easter week between 29 Mar and 05 Apr and St John’s Day 23/24 Jun)

          Season 1 – $2610 05 Jan – 30 Jun and 16 Sep – 13 Dec

          Season 2 – $3135 01 Jul – 15 Sep

          2027 06 Jan – 12 Dec (excl. Easter week between 21-28 Mar and St John’s Day 23/24 Jun)

          Season 1 – $2610 06 Jan – 30 Jun and 16 Sep – 12 Dec

          Season 2 – $2610 01 Jul – 15 Sep

          Worth noting We run this tour from Jan through to Dec. The summer months however (generally from 01 Jul – 15 Sep) can be really busy. More people, more cyclists, busier restaurants, busier hotels etc, so we’d recommend travelling in the Spring or Autumn if you‘re looking for a quieter getaway with less cyclists to share the route with.

          Please note We are generally not able to confirm any bookings for this tour made within 4 weeks of departure. Please contact our office if you are looking to book and begin your holiday within this period and we will do our best to accommodate your request.

          • Discovering Portugal’s most beautiful beaches
          • Cycling alongside the Ria de Aviero, a 40km stretch of blue lagoon
          • Helping the fishermen with their catch in Praia da Vieira
          • Enjoying the views of the western shoreline from the Sitio viewpoint
          • Exploring the historical, castle walled village of Óbidos
          • Visiting the lovely Vimeiro
          Photo Highlights Dates
          • 1
          • 2
          • Next page

          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
          Quote
          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
          Quote
          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
          Next

          News, Reviews & Stories

          Cycling on the Hadrian's Cycleway long distance cycle route

          7 Must-Do long distance cycle routes on the National Cycle Network

          If you’re looking for long distance cycle routes in the UK, you’ll likely have encountered the little blue and red signs marking the incredible National Cycle Network. For more than 30 years, Walk Wheel Cycle Trust has been the custodian of this network, developing and maintaining routes that make exploring the UK by bike more ...

          Amy McKie
          Amy McKie
          September 11, 2026
          Riding along the southern spain coastline on the badlands of spain

          9 must-ride Spanish cycling routes  

          Spanish cycling routes offer some of Europe's most rewarding riding, from dramatic mountain passes and quiet coastal roads to rolling vineyards and remote pueblos blancos (white villages). Few people know these bike tours in Spain better than Dan Hirst, Head of Skedaddle España. Dan has spent more than two decades living near Tarifa, mainland Spain's ...

          Dan Hirst, Head of Skedaddle Espana
          Dan Hirst
          September 4, 2026
          Cycling in the Pyrenees

          Cycling in the Pyrenees: A Tale of Two Journeys – France versus Spain

          The majestic Pyrenees mountain range, forming a natural border between France and Spain, has long attracted cyclists seeking both challenge and charm. Cycling in the Pyrenees offers exhilarating road cycling adventures, with stunning landscapes, diverse climates, and rich culture to discover. Skedaddle offers two distinct road cycling holidays through this rugged terrain. The Trans Pyrenees ...

          Hannah Reynolds
          September 4, 2026

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