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          2021 Cycling Tour Dates

          We found 116 Holidays in your search for:

          Destinations (74)
          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 (74)
          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 Tour Dates

          Page 3 of 12

          Select Order Order By
          Self-Guided
          Self-Guided
          Italy

          Sardinia - Coastal Explorer

          Self-Guided Road Bike Tour

          Duration

          8 days

          Prices from

          $2,110 P.P.
          View Reviews
          7
          1
          2
          3
          4
          5
          Grade 2 - 3: Gentle/Moderate
          More Info BOOK NOW

          Sardinia - Coastal Explorer

          Self-Guided Road Bike Tour

          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 29 Mar – 26 Oct (excluding dates from 08 Jun – 31 Aug)

          Season 1 – $2110 26 Mar – 07 Jun and 09 Sep – 29 Oct

          Season 2 – $2410 01 Sept – 08 Sept

          2027 30 Mar – 26 Oct (excluding dates from 08 Jun – 31 Aug)

          Season 1 – $2210 30 Mar – 07 Jun and 09 Sep – 26 Oct

          Season 2 – $2525 01 Sept – 08 Sept

          • Riding the stunning coastal road from Alghero to Bosa
          • Exploring the sandstone coast of Santa Caterina di Pittinuri
          • Visiting the Sinis Peninsula and the ancient Roman ruins of Tharros
          • The view of Pan di Zucchero on the Nebida coastal ride
          • Sweeping down the long descents to Fluminimaggiore and Masua
          • Exploring the white beaches running alongside the south west coastal road
          Photo Highlights Dates
          Self-Guided
          Self-Guided
          Italy

          Puglia - The Beautiful South

          Self-Guided Road Bike Tour

          Duration

          8 days

          Prices from

          $2,425 P.P.
          View Reviews
          2
          1
          2
          3
          4
          5
          Grade 2 : Gentle
          More Info BOOK NOW

          Puglia - The Beautiful South

          Self-Guided Road Bike Tour

          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 29 Mar – 26 Oct (excluding dates from 08 Jun – 31 Aug)

          Season 1 – $2425 29 Mar – 07 Jun / 09 Sep – 26 Oct

          Season 2 – $2795 01 Sept – 08 Sep

          2027 30 Mar – 26 Oct (excluding dates from 08 Jun – 31 Aug)

          Season 1 – $2535 30 Mar – 07 Jun / 09 Sep – 26 Oct

          Season 2 – $2925 01 Sep – 08 Sep

          • Savouring the deep red wine of the Salento region and the crisp whites of Locorotondo
          • Enjoying the sights of Alberobello, famous for the ‘trulli’
          • Exploring the gnarled olive groves in the countryside of Alberobello
          • Visiting 2 UNESCO heritage sites; Lecce and Alberobello
          • Admiring the Baroque churches of Lecce
          • Enjoying the panoramic coastal road between Santa Maria di Leuca and Otranto
          Photo Highlights Dates
          Guided
          Guided
          Portugal

          Vineyards of the Douro Valley

          Guided Road Bike Tour

          Duration

          8 days

          Prices from

          $3,850 P.P.
          View Reviews
          2
          1
          2
          3
          4
          5
          Grade 3 - 4: Moderate/ Challenging
          More Info BOOK NOW

          Vineyards of the Douro Valley

          Guided Road Bike Tour

          Start DateEnd DatePrice p.p.
          17/10/2026
          Last Spaces
          24/10/2026$3,850.00
          17/04/202724/04/2027$3,850.00
          09/10/202716/10/2027$3,850.00
          • Riding along the Douro river through immense vineyards surrounded by terraced slopes
          • Staying in carefully selected accommodations, with opportunities to visit Port wine cellars and taste local wines along the way.
          • Riding on the N222 in the heart of the Alto Douro, considered one of the most beautiful roads in the world, with its jaw dropping scenery
          • The historic fortified village of Almeida
          • Tackling the dramatic climb to the summit of Torre in the Serra da Estrela, the highest point of mainland Portugal
          • The final hotel at Unhais da Serra, an unexpected oasis at the end of the trip
          Photo Highlights Dates
          Guided
          Guided
          Portugal

          Atlantic Escape

          Guided Road Bike Tour

          Duration

          10 days

          Prices from

          $4,135 P.P.
          View Reviews
          11
          1
          2
          3
          4
          5
          Grade 3: Moderate
          More Info BOOK NOW

          Atlantic Escape

          Guided Road Bike Tour

          Start DateEnd DatePrice p.p.
          31/10/202609/11/2026$4,135.00
          01/05/202710/05/2027$4,135.00
          23/10/202701/11/2027$4,135.00
          • Stunning Sintra and its sunsets
          • The lovely fishing village of Nazare
          • Incredible accommodation in 4 star hotels each night
          • Views from the Arrabida mountains
          • Coastal riding and beautiful beaches
          • Reaching mainland Europe’s most southwesterly point by bike!
          Photo Highlights Dates
          Self-Guided
          Self-Guided
          Spain

          La Rioja - Ruta del Vino

          Self-Guided Road Bike Tour

          Duration

          7 days

          Prices from

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

          La Rioja - Ruta del Vino

          Self-Guided Road Bike Tour

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

          2026 – $1495 01 – 28 Mar / 05 Apr – 08 Jun / 10 Jun – 31 Jul / 1 Sep – 31 Oct

          2027 – $1540 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
          Guided
          Guided
          Spain

          La Rioja - Ruta del Vino

          Guided Road Bike Tour

          Duration

          7 days

          Prices from

          $3,280 P.P.
          View Reviews
          8
          1
          2
          3
          4
          5
          Grade 3: Moderate
          More Info BOOK NOW

          La Rioja - Ruta del Vino

          Guided Road Bike Tour

          Start DateEnd DatePrice p.p.
          27/09/2026
          Fully Booked
          03/10/2026$3,280.00
          07/06/202713/06/2027$3,350.00
          16/09/202722/09/2027$3,350.00
          • Staying at the fantastic San Millan de la Cogolla monastery, a World Heritage Site.
          • Cycling high along the limestone cliffs of the Sierra de Cantabria
          • Enjoying the atmospheric, medieval towns of Ezacary 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
          Guided
          Guided
          Spain

          Andalucia - Los Pueblos Blancos

          Guided Road Bike Tour

          Duration

          8 days

          Prices from

          $3,135 P.P.
          View Reviews
          5
          1
          2
          3
          4
          5
          Grade 2 - 3: Gentle/Moderate
          More Info BOOK NOW

          Andalucia - Los Pueblos Blancos

          Guided Road Bike Tour

          Start DateEnd DatePrice p.p.
          25/10/2026
          Contact Us
          01/11/2026$3,135.00
          28/12/202604/01/2027$3,565.00
          • 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
          Self-Guided
          Self-Guided
          Spain

          Andalucia - Los Pueblos Blancos

          Self-Guided Road Bike Tour

          Duration

          8 days

          Prices from

          $2,210 P.P.
          1
          2
          3
          4
          5
          Grade 2 - 3: Gentle/Moderate
          More Info BOOK NOW

          Andalucia - Los Pueblos Blancos

          Self-Guided Road Bike Tour

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

          2026 – $2210 – 01 Mar – 28 Mar / 05 Apr – 30 Jun / 08 Sep – 30 Nov

          • 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
          Guided
          Guided
          Spain

          Roads of Ronda

          Guided Road Bike Tour

          Duration

          7 days

          Prices from

          $3,035 P.P.
          View Reviews
          8
          1
          2
          3
          4
          5
          Grade 3: Moderate
          More Info BOOK NOW

          Roads of Ronda

          Guided Road Bike Tour

          Start DateEnd DatePrice p.p.
          08/11/2026
          Guaranteed
          14/11/2026$3,035.00
          • 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
          Self-Guided
          Self-Guided
          Spain

          Roads of Ronda

          Self-Guided Road Bike Tour

          Duration

          7 days

          Prices from

          $1,565 P.P.
          1
          2
          3
          4
          5
          Grade 3: Moderate
          More Info BOOK NOW

          Roads of Ronda

          Self-Guided Road Bike Tour

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

          2026 – $1565 – 01 Mar – 28 Mar / 05 Apr – 30 Apr / 03 May – 30 Jun / 08 Sep – 30 Nov

          • Staying in the quintessentially Spanish town of Ronda
          • Cycling through the rugged, ‘bandit country’ of the Sierra de las Nieves
          • Reaching the top of the stunning Puerto de las Palomas
          • Tasty tapas and sunset sangrias
          • White villages (pueblos blancos) cut into the hillsides
          • Planning your own cycling days based on our route notes and recommendations
          Photo Highlights Dates
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          Saddle Skedaddle staff were excellent. Consistently high standards delivered year on year. Don't think I'd trust anybody else when booking a cycling holiday!
          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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