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            2026 Cycling Holidays To Book Now

            We found 13 Holidays in your search for:

            Destinations (81)
            Types of Cycling / Grades (1)
            Departure Month

            2025

            2026

            2027

            Level of Support

            We found 13 Holidays in your search for:

            Select Order Order By
            Destinations (81)
            Types of Cycling / Grades (1)
            Departure Month

            2025

            2026

            2027

            Level of Support

            Are you ready to plan your cycling holiday for 2026? Here’s everything you can already book from our range to secure your space and mark it on your calendar. We’re working to make our full range available for 2026 bookings as soon as possible. If you don’t see something on the list, simply register your interest for your chosen trip or send our team a message, and we’ll keep you updated.

            We are also working on NEW routes and destinations for 2026. Be the first to find out more by signing up for our newsletter.

            • All Cycling Holidays
            • All Road Cycling Holidays
            • BOOK EARLY

            Page 1 of 2

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            Guided
            Guided
            Italy

            Grand Traverse Classic - North to South

            Guided Road Cycling Holiday

            Duration

            17 days

            Prices from

            £4,395 P.P.
            View Reviews
            9
            1
            2
            3
            4
            5
            Grade 4 : Challenging
            More Info BOOK NOW

            Grand Traverse Classic - North to South

            Guided Road Cycling Holiday

            Start DateEnd DatePrice p.p.
            22/05/2025
            Contact Us
            07/06/2025£4,395.00
            25/09/2025
            Last Spaces
            11/10/2025£4,395.00
            21/05/202606/06/2026£4,615.00
            24/09/202610/10/2026£4,615.00
            • Riding down 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: Lucca, San Gimignano, Pienza, Assisi and Lecce
            • 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 to the most southerly point of Italy, having ridden nearly 1,100 miles and climbed over 21,000 metres!
            Photo Highlights Dates
            Guided
            Guided
            France

            St Malo to Nice Classic

            Guided Road Cycling Holiday

            Duration

            15 days

            Prices from

            £4,195 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.
            * 15/06/2025
            Guaranteed
            29/06/2025£4,195.00
            06/09/202520/09/2025£4,195.00
            12/06/202626/06/2026£4,395.00
            04/09/202618/09/2026£4,395.00
            • 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
            Italy

            Alps and Dolomites - Giants of the Giro

            Guided Road Cycling Holiday

            Duration

            9 days

            Prices from

            £2,465 P.P.
            View Reviews
            17
            1
            2
            3
            4
            5
            Grade 4 - 5: Challenging/ Demanding
            More Info BOOK NOW

            Alps and Dolomites - Giants of the Giro

            Guided Road Cycling Holiday

            Start DateEnd DatePrice p.p.
            * 25/07/2025
            Fully Booked
            02/08/2025£2,465.00
            * 16/08/202524/08/2025£2,465.00
            24/07/202601/08/2026£2,595.00
            15/08/202623/08/2026£2,595.00
            • Cycling through the best alpine and dolomite scenery of Italy
            • Climbing the iconic Mortirolo, Passo Gavia and Passo Stelvio of Giro d’Italia fame
            • Enjoying post-ride relaxation in typical chalet-style mountain hotels
            • Re-charging your energy levels every evening with tasty local fayre
            • Testing your legs and endurance on the final Monte Grappa climb
            • Enjoying an aperitif in the lively towns of San Pellegrino Terme, Bormio and Bassano del Grappa
            Photo Highlights Dates
            Guided
            Guided
            Czech Republic, Austria, Slovenia & Italy

            NEW! Prague to Venice

            Guided Road Cycling Holiday

            Duration

            21 days

            Prices from

            £5,495 P.P.
            1
            2
            3
            4
            5
            Grade 3 : Moderate
            More Info BOOK NOW

            NEW! Prague to Venice

            Guided Road Cycling Holiday

            Start DateEnd DatePrice p.p.
            05/07/2025
            Last Spaces
            25/07/2025£5,495.00
            06/06/2026
            Last Spaces
            26/06/2026£5,775.00
            04/07/2026
            Fully Booked
            24/07/2026£5,775.00
            01/08/2026
            Last Spaces
            21/08/2026£5,775.00
            • A journey from Central Europe to the Mediterranean through four European countries
            • Visit the vibrant capitals of Prague, Vienna and Ljubljana
            • Learn about the historical Central European regions of Bohemia and Styria
            • Explore the UNESCO World Heritage sites of Prague, Cesky Krumlov, Vienna, Graz, and Venice
            • Have a well deserved end-of-ride pilsner seated in the village square of a little Bohemian village
            • Enjoy quiet countryside roads with sweeping views all the way from Prague to Vienna
            • Staying in quality accommodation, with warm traditional hospitality
            • Feast on the traditional dishes, desserts and drinks of the Czech, Austrian and Slovenian cuisine.
            Photo Highlights Dates
            Guided
            Guided
            Colombia

            Emerald Mountains

            Guided Road Cycling Holiday

            Duration

            13 days

            Prices from

            £3,875 P.P.
            View Reviews
            27
            1
            2
            3
            4
            5
            Grade 4 : Challenging
            More Info BOOK NOW

            Emerald Mountains

            Guided Road Cycling Holiday

            Start DateEnd DatePrice p.p.
            07/06/2025
            Contact Us
            19/06/2025£3,875.00
            17/01/202629/01/2026£3,995.00
            07/02/202619/02/2026£3,995.00
            06/06/202618/06/2026£3,995.00
            • 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
            Japan

            NEW! Shimanami Kaido, Shikoku & Kyoto

            Guided Road Cycling Holiday

            Duration

            15 days

            Prices from

            £7,595 P.P.
            1
            2
            3
            4
            5
            Grade 3 : Moderate
            More Info BOOK NOW

            NEW! Shimanami Kaido, Shikoku & Kyoto

            Guided Road Cycling Holiday

            Start DateEnd DatePrice p.p.
            22/10/2025
            Fully Booked
            05/11/2025£7,595.00
            09/05/202623/05/2026£7,795.00
            • Riding across the famous Shimanami Kaido cycling bridges
            • Traversing Shikoku’s quiet mountain roads and rolling coastline
            • Experiencing traditional Japanese cuisine, accommodations, and hospitality
            • Reaching Cape Ashizuri, the southernmost tip of Shikoku Island
            • Descending to the banks of the Shimanto River, one of Japan’s last unspoilt waterways
            • Passing through the magnificent Oboke and Koboke Gorges
            • Exploring Kyoto, Japan’s beautiful and historic cultural capital
            Photo Highlights Dates
            Guided
            Guided
            United Kingdom

            Land's End to John O'Groats Explorer

            Guided Road Cycling Holiday

            Duration

            22 days

            Prices from

            £4,845 P.P.
            View Reviews
            23
            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

            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.
            * 07/06/2025
            Last Spaces
            28/06/2025£4,845.00
            12/07/2025
            Last Spaces
            02/08/2025£4,845.00
            * 26/07/2025
            Guaranteed
            16/08/2025£4,845.00
            06/09/2025
            Last Spaces
            27/09/2025£4,845.00
            09/05/202630/05/2026£5,095.00
            11/07/202601/08/2026£5,095.00
            05/09/202626/09/2026£5,095.00
            • 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
            France

            St Malo to Nice Explorer

            Guided Road Cycling Holiday

            Duration

            20 days

            Prices from

            £5,725 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

            Start DateEnd DatePrice p.p.
            * 12/08/202531/08/2025£5,725.00
            11/05/202630/05/2026£5,995.00
            • 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
            Morocco

            Road Atlas

            Guided Road Cycling Holiday

            Duration

            10 days

            Prices from

            £1,765 P.P.
            View Reviews
            29
            1
            2
            3
            4
            5
            Grade 3 : Moderate
            More Info BOOK NOW

            Road Atlas

            Guided Road Cycling Holiday

            Start DateEnd DatePrice p.p.
            08/11/2025
            Last Spaces
            17/11/2025£1,765.00
            27/12/202505/01/2026£1,765.00
            31/01/202609/02/2026£1,855.00
            07/11/202616/11/2026£1,855.00
            27/12/202605/01/2027£1,855.00
            • 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

            £4,295 P.P.
            View Reviews
            12
            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.
            22/12/202503/01/2026£4,295.00
            14/03/202626/03/2026£4,295.00
            22/12/202603/01/2027£4,495.00
            • 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
            • 1
            • 2
            • Next page
            Quote
            After over 40 tours with other operators, I was apprehensive about trying a new company, but have come away extremely pleased with Skedaddle!
            Bruce, Italy - Sardinian Mountains
            Quote
            All queries were replied almost immediately! Well done, Skedaddle, you have provided good consultant, good tour leader and good technical assistant.
            Sin Siew Tag, 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
            Quite simply, there are not enough superlatives to describe how beautiful the Tuscan countryside and the accommodation chosen were!
            Robert, Italy - Tuscany Tourer
            Next

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