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            Cycling Holidays in Chile

            Sorry, no holidays found

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

            2026

            2027

            2028

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

            2026

            2027

            2028

            Level of Support

            Journey with us in South America on our cycling tours of Chile - a land of towering snow-capped volcanoes, crystal blue lakes, dense ancient forests and rolling vineyards with their Andean backdrop.

            Our cycling holidays in Chile will appeal to those who want to see rugged, open landscapes and truly stunning wildlife. Whether hoping to check out the famous local scenery, wanting to head far off the beaten track or you're looking to sample some of the delicious local wares during our vineyard tour, we’ve something to suit all cyclists. 

            • All Cycling Holidays
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            • South America Gravel Riding Holidays
            • Chile Gravel Riding Holidays
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            Sorry, no holidays found.

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

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

            Quote
            I’ve been fortunate enough to have ridden hundreds of days on a gravel bike all around the world and I can safely say that the first day of the Skedaddle Sardinia Cape to Cape trip was my all-time favourite.
            Olly, Italy - Sardinia Cape to Cape
            Quote
            A great gravel ride with variable terrain and stunning scenery. Skedaddle have managed to minimise the amount of tarmac riding in favour of much more interesting trails.
            Andrea, Spain - Badlands of Andalucia
            Quote
            An amazing trip exploring Tuscany mostly off-road which opens new vistas and experiences. Riding white gravel across the tops of hills with wide open skies and open hills all around was memorable.
            Miles, Italy - Strade Bianche Explorer
            Quote
            The riding was spectacular. Guides were good-humoured, fun, knowledgeable and lovely to chat to. I am grateful for being trusted to do my own thing and felt that I was still looked after. The flexibility to do this really made my holiday.
            Juliet, Scotland - Wild About Argyll
            Quote
            Fantastic area for cycling – really good, varied, fun tracks, beautiful places to ride. A mixture of easy riding along rivers and coast plus some challenging hill climbs. Girona and the surrounding area is beautiful.
            Anna, Spain - Girona Gravel Explorer
            Quote
            A most enjoyable trip in a beautiful part of the country that should appeal to a wide range of cyclists, not just gravel biking enthusiasts. Each day offered something different and was rewarding without being too challenging.
            Ian, UK - Northumberland Reivers Trails
            Next

            News, Reviews & Stories

            Meet the guides: Ernesto, Chile

            We take a closer look at our team in Chile who look after some of our most popular tours in South America. Meet our head honcho, Ernesto, who works tirelessly to ensure you all enjoy the best possible cycling experience across the pond. Read on to find out more about this friendly soul... 1. Name/nickname My ...

            Ernesto Palm
            December 1, 2025
            Carrera Lake in the Patagonia region of Chile

            The Story Behind: Carretera Austral & Lake District, Chile

            A little while ago we asked our maybes, newbies, and experienced Skedaddlers what their number one long-haul destination is. And Chile rode out as the clear winner. It was news to celebrate for us and all the inspiration we needed to create our  latest trip in Patagonia, the Carretera Austral. A trip that’s been described ...

            Andrew Straw Co-Founder of Saddle Skedaddle
            Ernesto Palm & Andrew Straw
            November 10, 2025
            Paul Snedker and Andrew Straw cycling in Chile where Saddle Skedaddle formed an idea

            The Story Behind: Chile, Skedaddle’s spiritual home

            Two old friends on one momentous year-long trip. The ingredients that inspired a lifelong passion for pedallin’. For Saddle Skedaddle’s co-founders, Andrew Straw (Straws) and Paul Snedker, their journey through Chile was so packed with unforgettable people, places and moments that they never stopped travelling by bike and exploring the world with others. Inspiring beginnings: Where ...

            Andrew Straw Co-Founder of Saddle Skedaddle
            Paul Snedker & Andrew Straw
            June 27, 2020

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