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            Winter Road Cycling Holidays

            We found 6 Holidays in your search for:

            Destinations (83)
            Types of Cycling / Grades (1)
            Departure Month

            2026

            2027

            2028

            Level of Support

            We found 6 Holidays in your search for:

            Select Order Order By
            Destinations (83)
            Types of Cycling / Grades (1)
            Departure Month

            2026

            2027

            2028

            Level of Support

            Whether you're looking to snap up a last minute spot on one of our guaranteed departures this late season, or are casting your mind ahead to next year - we've got plenty of popular pedallin' options across the globe to get you excited!

            • All Cycling Holidays
            • All Road Cycling Holidays
            • Road Winter Sun
            Select Order Order By
            Guided
            £100 OFF
            Guided
            Morocco

            Road Atlas

            Guided Road Cycling Holiday

            Duration

            10 days

            Prices from

            £1,895 P.P.
            View Reviews
            30
            1
            2
            3
            4
            5
            Grade 3 : Moderate
            More Info BOOK NOW

            Road Atlas

            Guided Road Cycling Holiday

            Start DateEnd DatePrice p.p.
            07/11/2026
            Fully Booked
            		16/11/2026£1,895.00
            27/12/2026
            Contact Us
            		05/01/2027£1,895.00
            30/01/2027
            Guaranteed
            		08/02/2027£1,995.00
            06/11/2027
            £100 OFF
            		15/11/2027£1,995.00
            27/12/2027
            £100 OFF
            		05/01/2028£1,995.00
            • 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
            Costa Rica

            Ruta de los Volcanes

            Guided Road Cycling Holiday

            Duration

            13 days

            Prices from

            £4,395 P.P.
            View Reviews
            13
            1
            2
            3
            4
            5
            Grade 3 : Moderate
            More Info BOOK NOW

            Ruta de los Volcanes

            Guided Road Cycling Holiday

            Start DateEnd DatePrice p.p.
            22/12/2026
            Contact Us
            		03/01/2027£4,395.00
            13/03/202725/03/2027£4,425.00
            22/12/202703/01/2028£4,525.00
            • 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
            Colombia

            Emerald Mountains

            Guided Road Cycling Holiday

            Duration

            13 days

            Prices from

            £4,195 P.P.
            View Reviews
            28
            1
            2
            3
            4
            5
            Grade 4 : Challenging
            More Info BOOK NOW

            Emerald Mountains

            Guided Road Cycling Holiday

            Start DateEnd DatePrice p.p.
            16/01/2027
            Guaranteed
            		28/01/2027£4,195.00
            06/02/2027
            Guaranteed
            		18/02/2027£4,195.00
            15/01/202827/01/2028£4,395.00
            05/02/202817/02/2028£4,395.00
            • 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
            Spain

            Roads of Ronda

            Guided Road Cycling Holiday

            Duration

            7 days

            Prices from

            £2,125 P.P.
            View Reviews
            9
            1
            2
            3
            4
            5
            Grade 3 : Moderate
            More Info BOOK NOW

            Roads of Ronda

            Guided Road Cycling Holiday

            Start DateEnd DatePrice p.p.
            08/11/2026
            Last Spaces
            		14/11/2026£2,125.00
            • Staying in the quintessentially Spanish town of Old Ronda
            • Cycling through the rugged, ‘bandit country’ of the Sierra de las Nieves
            • Climbing the 1,200m up ‘The Colossus’
            • The seemingly never-ending descent down to the fine sands of Estepona
            • Taking a refreshing post ride dip in the Med
            • Tasty tapas and sunset sangrias
            Photo Highlights Dates
            Guided
            Guided
            Chile and Argentina

            The Andes and the Lake District

            Guided Road Cycling Holiday

            Duration

            13 days

            Prices from

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

            The Andes and the Lake District

            Guided Road Cycling Holiday

            Start DateEnd DatePrice p.p.
            13/03/2027
            Guaranteed
            		25/03/2027£4,135.00
            23/10/202704/11/2027£4,485.00
            11/03/202823/03/2028£4,485.00
            • Your first glimpse of the snowcapped Volcan Osorno
            • Crossing over the Andes not just once but twice!
            • Cycling the Seven Lakes Route from San Martin to Villa Angostura
            • Quiet roads and the backdrop of the awesome Andes
            • The immense monkey puzzle trees around Villa Pehuenia
            • Relaxing in the Puyehue hot springs
            • Tasting all the culinary delights of the region
            Photo Highlights Dates
            Guided
            £125 OFF
            Guided
            Spain

            Andalucia - Los Pueblos Blancos

            Guided Road Cycling Holiday

            Duration

            8 days

            Prices from

            £2,495 P.P.
            View Reviews
            5
            1
            2
            3
            4
            5
            Grade 2 - 3: Gentle to Moderate
            More Info BOOK NOW

            Andalucia - Los Pueblos Blancos

            Guided Road Cycling Holiday

            Start DateEnd DatePrice p.p.
            28/12/2026
            £125 OFF
            		04/01/2027£2,495.00
            • 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

            Not sure which trip's right for you? Just ask!

            Get in touch and we'll help you find your perfect trip.

            Quote
            100% perfection from Saddle Skedaddle on a recent road tour. Amazing route, exceptional accommodation, brilliant guides, quality hire bikes.....11 out of 10!
            Andy - Puglia to Cilento
            Quote
            All queries were replied almost immediately! Well done, Skedaddle, you have provided good consultant, good tour leader and good technical assistant.
            Sin Siew - UK, Land's End to John O'Groats
            Quote
            This trip had something for everybody! The crew were fantastic, they were a vital part of the trip. The rest was the magic of Italy.
            Nigel, Italy - Grand Traverse
            Quote
            A fantastic journey of a lifetime led by excellent guides. Loved the Gorge du Verdon - tremendous climb and stupendous view.
            Miles, France - St Malo to Nice
            Quote
            I was the least experienced in the group - but was made to feel very comfortable and given lots of instruction and help.
            Catharine, France - Le Ventoux a Velo
            Quote
            The trip was amazing and exceeded my expectations. The route was spectacular and well thought, a perfect mix of challenges and easier days to cater for different abilities, levels of fitness and recovery times, without ever being boring.
            Lisa - Colombia Emerald Mountains
            Next

            News, Reviews & Stories
            Cyclist overlooking Lake Jasna in Slovenia

            Why cycling in Slovenia deserves a spot on your wishlist 

            Slovenia features as a highlight on our popular Prague to Venice iconic journey, where riders spend several days cycling through this beautiful corner of Europe. For 2027, we're excited to introduce two brand-new Slovenia cycling tours that explore even more of this remarkable European destination. As a keen cyclist and self-confessed Balkan enthusiast, cycling in Slovenia ...

            Fran on the C2C
            Fran Wilson
            October 29, 2026
            Cyclists riding in Sweden on the Coastal Kattegattleden cycle route

            6 Reasons To Cycle In Sweden

            Our holidays in Sweden are some of the most popular in our leisure cycling range. We're excited to introduce a brand new guided group holiday for 2027 cycling the Kattegattleden, Sweden's first national cycle path. Read on to learn more about our tours and six reasons why you'll love cycling in Sweden. Coastal Kattegattleden The 8-day ...

            Paul Snedker
            Paul Snedker
            October 15, 2026
            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

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