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            2027 Road Cycling Holidays To Book Now

            We found 16 Holidays in your search for:

            Destinations (82)
            Types of Cycling / Grades (1)
            Departure Month

            2026

            2027

            2028

            Level of Support

            We found 16 Holidays in your search for:

            Select Order Order By
            Destinations (82)
            Types of Cycling / Grades (1)
            Departure Month

            2026

            2027

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            Level of Support
            2027 Road Cycling Holidays 2027 Adventure Cycling Holidays 2027 Leisure Cycling Holidays 2027 Mountain Bike Holidays

            Planning ahead for your dream cycling holiday? 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 in 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 Road Cycling Holidays
            • BOOK EARLY

            Page 1 of 2

            Select Order Order By
            Guided
            Guided
            Colombia

            Emerald Mountains

            Guided Road Cycling Holiday

            Duration

            13 days

            Prices from

            £3,995 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.
            06/06/2026
            Contact Us
            18/06/2026£3,995.00
            16/01/202728/01/2027£4,195.00
            06/02/202718/02/2027£4,195.00
            05/06/202717/06/2027£4,195.00
            • 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
            United Kingdom

            Land's End to John O'Groats Classic

            Guided Road Cycling Holiday

            Duration

            16 days

            Prices from

            £3,295 P.P.
            View Reviews
            20
            1
            2
            3
            4
            5
            Grade 3 - 4: Moderate/ Challenging
            More Info BOOK NOW

            Land's End to John O'Groats Classic

            Guided Road Cycling Holiday

            LAST CHANCE OFFERS!

            Choose half-price bike hire or get 5% off tour departing 22 Aug 2026. Book before 01 June 2026 and enter promo code LETSGO26. Your discount will be applied once your booking is confirmed. Ts and Cs apply.

            Start DateEnd DatePrice p.p.
            23/05/2026
            Last Spaces
            07/06/2026£3,295.00
            * 22/08/2026
            Last Spaces
            06/09/2026£3,295.00
            22/05/2027
            Guaranteed
            06/06/2027£3,395.00
            14/08/202729/08/2027£3,395.00
            • Ride the length of Britain from toe to tip and declare yourself an ‘End to Ender’
            • The camaraderie of completing the UK’s best challenge ride on a small group tour
            • 3 countries in 14 days of riding. 1,000 miles of Britain at its best
            • A unique LEJOG route along quiet roads through scenic countryside
            • Enjoy spectacular scenery from Cheddar Gorge to the Cairngorms
            • Experience the regional changes in tradition, culture and accents as you progress from county to county
            • Delicious picnics, country pubs and wonderful accommodation
            • Cornish pasties to haggis and everything in between
            Photo Highlights Dates
            Guided
            Guided
            France

            St Malo to Nice Explorer

            Guided Road Cycling Holiday

            Duration

            20 days

            Prices from

            £5,895 P.P.
            View Reviews
            19
            1
            2
            3
            4
            5
            Grade 3 : Moderate
            More Info BOOK NOW

            St Malo to Nice Explorer

            Guided Road Cycling Holiday

            LAST CHANCE OFFERS!

            Choose half-price bike hire or get 5% off tour departing 07 Sep 2026. Book before 01 June 2026 and enter promo code LETSGO26. Your discount will be applied once your booking is confirmed. Ts and Cs apply.

            Start DateEnd DatePrice p.p.
            * 07/09/202626/09/2026£5,895.00
            25/05/202713/06/2027£6,075.00
            06/09/202725/09/2027£6,075.00
            • Cycling along the Brittany coast with views out to the Abbey of Mont St-Michel
            • Travelling under your own power all the way from the Channel to the Mediterranean
            • Meandering along the Loire, Dordogne and Rhône rivers
            • Riding through vineyards of Chateauneuf-du-pape
            • Riding through the lavender fields of Provence and winding your way through the Verdon Gorge
            • Descending to Nice to ride along the Promenade des Anglais
            Photo Highlights Dates
            Guided
            Guided
            Italy

            Grand Traverse Explorer - South to North

            Guided Road Cycling Holiday

            Duration

            22 days

            Prices from

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

            Grand Traverse Explorer - South to North

            Guided Road Cycling Holiday

            Start DateEnd DatePrice p.p.
            29/08/2026
            Guaranteed
            19/09/2026£5,495.00
            24/04/202715/05/2027£5,655.00
            28/08/202718/09/2027£5,655.00
            • Riding up the backbone of Italy on a stunning route which takes in some of the best road cycling that Italy has to offer
            • Cycling through 10 UNESCO World Heritage sites and 5 National Parks
            • Visiting some of the most important historical and artistic cities in Italy: Lecce, Assisi, Siena, Venice
            • The camaraderie of your fellow cyclists who’ll be joining you on this incredible tour
            • Immersing yourself in Italian culture – meeting the friendly locals, experiencing delicious culinary specialties and tasting the wines of each region
            • Cycling from the most south-easterly point of the heel of Italy up to Venice, having ridden nearly 1,100 miles and climbed almost 22,000 metres!
            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
            3
            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.
            24/10/2026
            Guaranteed
            05/11/2026£4,135.00
            13/03/202725/03/2027£4,135.00
            • 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
            Guided
            United Kingdom

            Land's End to John O'Groats Explorer

            Guided Road Cycling Holiday

            Duration

            22 days

            Prices from

            £4,895 P.P.
            View Reviews
            25
            1
            2
            3
            4
            5
            Grade 3 - 4: Moderate/ Challenging
            More Info BOOK NOW

            Land's End to John O'Groats Explorer

            Guided Road Cycling Holiday

            LAST CHANCE OFFERS!

            Choose half-price bike hire or get 5% off tour departing 5 Sep 2026. Book before 01 June 2026 and enter promo code LETSGO26. Your discount will be applied once your booking is confirmed. Ts and Cs apply.

            Start DateEnd DatePrice p.p.
            06/06/2026
            Fully Booked
            27/06/2026£4,895.00
            11/07/2026
            Last Spaces
            01/08/2026£4,895.00
            * 05/09/2026
            Last Spaces
            26/09/2026£4,895.00
            08/05/202729/05/2027£5,045.00
            05/06/202726/06/2027£5,045.00
            03/07/202724/07/2027£5,045.00
            31/07/202721/08/2027£5,045.00
            • Ride the length of Britain from toe to tip and declare yourself an ‘End to Ender’
            • Experience the regional changes in tradition, culture and accents as you progress from county to county
            • Enjoy spectacular scenery from Cheddar Gorge to the Cairngorms
            • 3 countries in 19 days of riding
            • 1,000 miles of Britain at its best
            • Cornish pasties to haggis and everything in between
            Photo Highlights Dates
            Guided
            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
            Guaranteed
            16/11/2026£1,895.00
            27/12/202605/01/2027£1,895.00
            30/01/202708/02/2027£1,995.00
            06/11/202715/11/2027£1,995.00
            27/12/202705/01/2028£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.
            22/12/202603/01/2027£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
            France

            St Malo to Nice Classic

            Guided Road Cycling Holiday

            Duration

            15 days

            Prices from

            £4,395 P.P.
            View Reviews
            15
            1
            2
            3
            4
            5
            Grade 3 - 4: Moderate/ Challenging
            More Info BOOK NOW

            St Malo to Nice Classic

            Guided Road Cycling Holiday

            Start DateEnd DatePrice p.p.
            12/06/2026
            Contact Us
            26/06/2026£4,395.00
            14/08/2026
            Contact Us
            28/08/2026£4,395.00
            18/06/202702/07/2027£4,525.00
            13/08/202727/08/2027£4,525.00
            • Cycling along the Brittany coast with views out to the Abbey of Mont St Michel
            • Travelling under your own power all the way from the Channel to the Mediterranean
            • Following riverside roads along the Loire, Dordogne and the Rhône
            • Riding through the wine drenched Châteauneuf-du-Pape!
            • Riding through the lavender fields of Provence and winding your way through the Verdon Gorge
            • Descending to Nice to ride along the Promenade des Anglais like a Tour de France winner!
            Photo Highlights Dates
            Guided
            Guided
            Scotland

            Scotland - Tour d'Ecosse

            Guided Road Cycling Holiday

            Duration

            8 days

            Prices from

            £1,855 P.P.
            View Reviews
            8
            1
            2
            3
            4
            5
            Grade 3 : Moderate
            More Info BOOK NOW

            Scotland - Tour d'Ecosse

            Guided Road Cycling Holiday

            Start DateEnd DatePrice p.p.
            23/05/2026
            Last Spaces
            30/05/2026£1,855.00
            13/06/2026
            Fully Booked
            20/06/2026£1,855.00
            04/07/2026
            Last Spaces
            11/07/2026£1,855.00
            08/08/2026
            Last Spaces
            15/08/2026£1,855.00
            05/09/2026
            Guaranteed
            12/09/2026£1,855.00
            08/05/202715/05/2027£1,925.00
            26/06/202703/07/2027£1,925.00
            07/08/202714/08/2027£1,925.00
            04/09/202711/09/2027£1,925.00
            • Quiet single-track roads for miles on end
            • Bealach Na Ba – the greatest road ascent in the UK
            • Feasting on fresh seafood after a day in the saddle
            • Stunning views out over the Isle of Skye
            • Cycling the peaceful lochside roads of Scotland
            • The swooping coastal road from Ullapool to Kinlochewe
            Photo Highlights Dates
            • 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
            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

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