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            2021 Cycling Holiday Dates

            We found 116 Holidays in your search for:

            Destinations (82)
            Types of Cycling / Grades (7)
            Departure Month

            2026

            2027

            2028

            Level of Support

            We found 116 Holidays in your search for:

            Select Order Order By
            Destinations (82)
            Types of Cycling / Grades (7)
            Departure Month

            2026

            2027

            2028

            Level of Support

            With 2020 in full swing and lots of travel uncertainty at the minute, we wanted  to get some of our 2021 dates launched accross our range to give you more options to choose from - and help inspire you during this difficult time! What better way to help you feel motivated than by getting some good times on the bikes booked in...

            • All Cycling Holidays
            • 2021 Cycling Holiday Dates

            Page 10 of 12

            Select Order Order By
            Self-Guided
            Self-Guided
            Spain

            La Rioja - Ruta del Vino

            Self-Guided Road Cycling Holiday

            Duration

            7 days

            Prices from

            £1,045 P.P.
            1
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            Grade 3 : Moderate
            More Info BOOK NOW

            La Rioja - Ruta del Vino

            Self-Guided Road Cycling Holiday

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

            2026 – £1045 01 – 28 Mar / 05 Apr – 08 Jun / 10 Jun – 31 Jul / 1 Sep – 31 Oct

            2027 – £1075 01 – 18 Mar / 29 Mar – 08 Jun / 10 Jun – 31 Jul / 1 Sep – 31 Oct

            • The fantastic San Millan de la Cogolla monastery, a World Heritage Site
            • Marvelling at Frank Gehry’s architectural genius at the Marques de Riscal Winery on the loop ride from Laguardia
            • Cycling high along the limestone cliffs of the Sierra de Cantabria
            • Enjoying the atmospheric, medieval towns of Ezcaray and Laguardia
            • Wine tasting in a Riojan bodega (or two!)
            • Cycling through Mediterranean forests, along mountainsides and through endless vineyards
            • Rolling along the Rio Ebro into Logroño for an authentic slice of tapas heaven in Calle Laurel
            Photo Highlights Dates
            Self-Guided
            Self-Guided
            Italy

            Sicily

            Self-Guided Leisure Cycling Holiday

            Duration

            8 days

            Prices from

            £1,695 P.P.
            View Reviews
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            Grade 2: Gentle
            More Info BOOK NOW

            Sicily

            Self-Guided Leisure Cycling Holiday

            E-BIKE HIRE AVAILABLE

            This holiday is well-suited to both normal bikes and pedal assist e-bikes and you can choose to hire either when you book your holiday 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 applicable for all start dates between and inclusive of the stated dates.

            2026 29 Mar – 26 Oct (excluding departures from 08 Jun – 31 August)

            Season 1 – £1695 29 Mar – 07 Jun and 09 Sep – 26 Oct

            Season 2 – £1995 01 Sep – 08 Sep

            2027 30 Mar – 26 Oct (excluding departures from 08 Jun – 31 August)

            Season 1 – £1775 30 Mar – 07 Jun and 09 Sep – 26 Oct

            Season 2 – £2095 01 Sep – 08 Sep

            • Visiting the Baroque towns of Modica, Ragusa and Noto, all UNESCO Heritage Sites
            • Sampling delicious Sicilian pastries, like cannoli and cassata
            • Cycling along the beautiful coastal road to Capo Passero
            • Exploring the medieval streets of Ortigia di Siracusa
            • Enjoying an aperitivo ‘al fresco’ with the locals in one of the many piazzas
            • Discovering the astonishing Oasis of Vendicari
            Photo Highlights Dates
            Guided
            Guided
            Spain

            Bilbao to Santiago

            Guided Road Cycling Holiday

            Duration

            11 days

            Prices from

            £3,295 P.P.
            View Reviews
            4
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            Grade 3 : Moderate
            More Info BOOK NOW

            Bilbao to Santiago

            Guided Road Cycling Holiday

            Start DateEnd DatePrice p.p.
            26/06/202706/07/2027£3,295.00
            05/09/202715/09/2027£3,295.00
            • Riding along the stunning and dramatic Cantabrian coastline
            • Enjoying a fabulous seafood platter in San Vicente de Barquera
            • Pouring cider in the old town of Oviedo
            • Arriving at the roof of the ‘Camino Primitivo‘, Puerto Palo
            • Cycling through beautiful, rural, enchanting Galicia to arrive in historical Santiago to collect a pilgrims’ certificate
            • The arrival at ‘the end of the world’ and awesome Cape Finisterre
            Photo Highlights Dates
            Guided
            Guided
            Italy

            Dolomites of Brenta

            Guided Electric Mountain Bike Holiday

            Duration

            7 days

            Prices from

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

            Dolomites of Brenta

            Guided Electric Mountain Bike Holiday

            ELECTRIC MOUNTAIN BIKE HOLIDAY

            If you love mountain biking let us show you the thrills of an e-MTB adventure. On this specially designed holiday we’ll be making the most of everything an e-MTB has to offer, with incredible climbs as well as fun descents. Hire one of our quality e-mountain bikes and experience the buzz of a pedal-assisted ride. Remember to select your e-MTB hire when you book a holiday with us.

            Start DateEnd DatePrice p.p.
            19/06/202725/06/2027£2,395.00
            24/07/202730/07/2027£2,395.00
            • Everchanging mountain scenery
            • Scrumptious polenta and stew at the best little refuge of the Dolomites
            • Gazing over the most famous peaks of the Dolomites
            • Rolling through alpine pastures
            • Italian gelato after a day on your bike
            • Biking through beech forests and flower filled meadows
            Photo Highlights Dates
            Self-Guided
            Self-Guided
            Portugal

            Alentejo and the Algarve

            Self-Guided Leisure Cycling Holiday

            Duration

            8 days

            Prices from

            £2,175 P.P.
            View Reviews
            3
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            Grade 3-4 : Moderate/Active
            More Info BOOK NOW

            Alentejo and the Algarve

            Self-Guided Leisure 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.

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

            2026 – £2175 Sunday departures available

            11 Jan to 21 Jun and 20 Sep – 06 Dec

            (No departures over the Easter week 29 Mar – 05 Apr, St John’s Day 23/24 Jun and over the hotter / busier summer months)

            2027 – £2175 Sunday departures available

            10 Jan to 20 Jun and 19 Sep – 05 Dec

            (No departures over the Easter week 21-28 Mar)and over the hotter / busier summer months)

            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.

            • Warming up with a loop ride through the Arrábida Natural Park
            • Catching the ferry across to Troia and enjoying the quiet road along the Troia peninsula
            • Enjoying the spectacular road along the coast near Porto Covo
            • Visiting the Cabo Sardão lighthouse and enjoying the shore-line views of the wild cliffs
            • Taking a dip on isolated beaches at the bottom of spectacular cliffs
            • Discovering the city of Lagos in the Algarve, with its amazing mixture of tradition and tourism
            • Visiting Cape St Vincent, Europe’s most southwestern point and its imposing lighthouse
            • Wondering at the splendour of the high cliffs around Sagres
            Photo Highlights Dates
            Self-Guided
            Self-Guided
            Italy

            Emilia-Romagna - The Food Valley

            Self-Guided Leisure Cycling Holiday

            Duration

            8 days

            Prices from

            £1,575 P.P.
            View Reviews
            6
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            Grade 2-3: Gentle/Moderate
            More Info BOOK NOW

            Emilia-Romagna - The Food Valley

            Self-Guided Leisure Cycling Holiday

            E-BIKE HIRE AVAILABLE

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

            2026 29 Mar – 26 Oct (excluding dates throughout July and August)

            Season 1 – £1575 29 Mar – 14 Jun and 09 Sep – 26 Oct

            Season 2 – £1695 15 – 30 Jun and 01 – 08 Sep

            2027 30 Mar – 26 Oct (excluding dates throughout July and August)

            Season 1 – £1650 30 Mar – 14 Jun and 09 Sep – 26 Oct

            Season 2 – £1775 15 – 30 Jun and 01 – 08 Sep

            To ensure you have the best experience possible, we’d recommend travelling in the Spring or in the Autumn. We don’t as standard offer this tour in the hotter, more humid, busier summer months of July and August. If however your dates are set in July or August, please call us for a chat and we’ll do what we can to accommodate you.

            • Gently cycling on quiet roads and cycle paths through beautiful countryside
            • Sampling tasty slow-food produce on the Food Valley Bike route from Cremona to Parma
            • Tasting authentic Italian food in their towns of origin such as Parma Ham, Parmigiano Reggiano, Balsamic Vinegar, and Bolognese Ragù
            • Visiting the hometown of the famous Italian composer Giuseppe Verdi
            • Exploring modern and bustling Modena
            • Taking in the vibrant university city of Bologna
            Photo Highlights Dates
            Self-Guided
            Self-Guided
            Ireland

            Highlights of Kerry

            Self-Guided Leisure Cycling Holiday

            Duration

            8 days

            Prices from

            £1,595 P.P.
            View Reviews
            1
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            Grade 3-4 : Moderate/Active
            More Info BOOK NOW

            Highlights of Kerry

            Self-Guided Leisure Cycling Holiday

            E-BIKE HIRE AVAILABLE

            This holiday is well-suited to both normal bikes and pedal assist e-bikes and you can choose to hire either when you book your holiday 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.

            2026 Daily departures available from 01 Apr to 10 Oct.

            £1595 per person.

            Please note we are generally not able to confirm any bookings for this tour made within 2 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.

            • Cycling the foothills of Ireland’s highest Mountain – Carrantuohill
            • Exploring the picturesque shores of Kells Bay
            • Dining in cosy Irish pubs
            • Enjoying views over the spectacular Three Lakes of Killarney
            • Riding through the renowned Gap of Dunloe
            • Visiting Valentia Island and discovering 360-million-year-old Tetrapod footprints.
            Photo Highlights Dates
            Guided
            Guided
            Spain

            Sierras Explorer

            Guided Mountain Bike Holiday

            Duration

            7 days

            Prices from

            £2,095 P.P.
            View Reviews
            2
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            Grade 3 : Moderate
            More Info BOOK NOW

            Sierras Explorer

            Guided Mountain Bike Holiday

            E-MTB HIRE AVAILABLE

            This holiday is great fun on a regular mountain bike or an e-mountain bike and you can choose to hire either when you book your holiday with us! If you’re an experienced rider, you can choose one of our quality e-mountain hire bikes and experience the buzz of a pedal-assisted ride. Select your e-MTB hire when you book a holiday with us. Bear in mind that the pace will be set to riders with a regular mountain bike.

            Start DateEnd DatePrice p.p.
            31/10/2026
            Guaranteed
            06/11/2026£2,095.00
            • Exploring the historical town of Ronda
            • Riding the slick Guadiaro single-track
            • Incredible descent through the Alcornocales to the white hilltop of Jimena
            • Spending a night in the beautiful setting of a 13th century Moorish castle
            • Riding the shores of the Straits of Gibraltar past secluded coves and ancient watchtowers
            • Tapas bar hopping in the fun filled town of Tarifa
            Photo Highlights Dates
            Guided
            Guided
            Scotland

            Scotland - Lochs and Glens

            Guided Leisure Cycling Holiday

            Duration

            7 days

            Prices from

            £1,655 P.P.
            View Reviews
            4
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            Grade 3-4 : Moderate/Active
            More Info BOOK NOW

            Scotland - Lochs and Glens

            Guided Leisure 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.
            09/05/202715/05/2027£1,655.00
            13/06/202719/06/2027£1,655.00
            15/08/202721/08/2027£1,655.00
            • Watching the sun rise over Loch Lomond
            • The beautiful lochs of Venachar, Lubnaig and Tay
            • Cycling through the dramatic Cairngorms National Park
            • Scottish wildlife at its best including deer, red squirrels, eagles and osprey
            • Castles and distilleries galore
            • Rural Scottish cycling at its very best
            Photo Highlights Dates
            Self-Guided
            Self-Guided
            Spain

            Bilbao to San Sebastian

            Self-Guided Leisure Cycling Holiday

            Duration

            7 days

            Prices from

            £1,695 P.P.
            View Reviews
            2
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            Grade 3 : Moderate
            More Info BOOK NOW

            Bilbao to San Sebastian

            Self-Guided Leisure Cycling Holiday

            E-BIKE HIRE AVAILABLE

            This holiday 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 06 Apr – 31 Oct (excluding dates from 01 – 31 Aug and 11 – 20 Sep)

            Season 1 – £1695 06 – 29 Apr / 03 May – 11 Jun / 1 – 31 Oct

            Season 2 – £1925 30 Apr – 02 May / 12 Jun – 25 Jul / 01 – 10 Sep / 21 – 30 Sep

            2027 30 Mar – 31 Oct (excluding dates from 25 Jul – 31 Aug)

            Season 1 – £1695 30 Mar – 29 Apr / 3 May – 10 Jun / 21 Sep – 31 Oct

            Season 2 – £1925 30 Apr – 02 May / 11 Jun – 25 Jul / 01 – 10 Sep

            Alternatively for a great value holiday choose one of our scheduled departures below.

            • Visiting the world-class Guggenheim museum
            • Savouring fabulous Basque cuisine
            • Cycling through the beautiful Urdaibai natural park
            • Admiring the dramatic Atlantic coastline: Cliffs, beaches, estuaries and coves
            • Relaxing by the harbour of the picturesque fishing village of Lekeitio
            • Arriving in stunning San Sebastian and bar hopping in the Casco Viejo
            Photo Highlights Dates
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            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
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            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
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            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
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            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
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            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
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            News, Reviews & Stories

            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

            5 best end to end cycle routes 

            There is something undeniably special about cycling the full length of a country. More than just a cycling holiday, these epic journeys allow you to experience a destination in a way few travellers ever do, watching landscapes and cultures change day by day from the saddle. For Skedaddle Travel Consultant Kerry Ashberry, our Iconic Journeys ...

            Kerry Ashberry
            August 21, 2026

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