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    • NEW! - Scotland - The Heart of Galloway
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          Grand Tour Inspired Cycling Tours

          We found 18 Holidays in your search for:

          Destinations (75)
          Types of Cycling / Grades (7)
          Departure Month

          2026

          2027

          2028

          Level of Support

          We found 18 Holidays in your search for:

          Select Order Order By
          Destinations (75)
          Types of Cycling / Grades (7)
          Departure Month

          2026

          2027

          2028

          Level of Support

          One of the things we love about road cycling is that it allows us to follow in the footsteps of our cycling heroes, experiencing the thrill of conquering iconic climbs and sharing that sense of achievement after finishing an epic tour over some of the world’s most famous mountain passes. Whether you’re seeking a long-distance route for that ultimate grand tour feeling or a challenging route that ticks off classics like Stelvio, Tourmalet or Ventoux, these tours are guaranteed to inspire.

          Fully supported, our tours are meticulously planned leaving you to focus on what matters - the joy of the ride.

          • All Cycling Holidays
          • Grand Tour Inspired Cycling Tours

          Page 2 of 2

          Select Order Order By
          Guided
          $300 OFF
          Guided
          Spain

          Basque Country to Andalucia Explorer - North to South

          Guided Road Bike Tour

          Duration

          21 days

          Prices from

          $7,650 P.P.
          View Reviews
          2
          1
          2
          3
          4
          5
          Grade 3: Moderate
          More Info BOOK NOW

          Basque Country to Andalucia Explorer - North to South

          Guided Road Bike Tour

          Start DateEnd DatePrice p.p.
          08/05/2027
          $300 OFF
          28/05/2027$7,650.00
          28/08/2027
          $300 OFF
          17/09/2027$7,650.00
          • Starting in style with a Pintxos tour in elegant San Sebastian
          • Cycling through the vineyards & dramatic mountains of Rioja
          • Spending an evening in the Monastery of Valvanera
          • Seduced by Segovia with its castle and cathedral
          • Descending from the Sierras to the charming beauty of Cordoba
          • Finishing your ride in style at the fun loving city of Malaga
          Photo Highlights Dates
          Guided
          $400 OFF
          Guided
          Spain & Portugal

          Trans Iberia - Barcelona to Porto

          Guided Road Bike Tour

          Duration

          22 days

          Prices from

          $8,250 P.P.
          View Reviews
          3
          1
          2
          3
          4
          5
          Grade 3 - 4: Moderate/ Challenging
          More Info BOOK NOW

          Trans Iberia - Barcelona to Porto

          Guided Road Bike Tour

          Start DateEnd DatePrice p.p.
          03/10/2026
          Last Spaces
          24/10/2026$8,250.00
          09/04/2027
          $400 OFF
          30/04/2027$8,490.00
          05/10/2027
          $400 OFF
          26/10/2027$8,490.00
          • Starting the journey in the cultural capital of Barcelona
          • Crossing the stunning mountain roads of the Sierra de Gredos
          • Delighting in the varied regional specialities of the Iberian Peninsula
          • Discovering the fortified city of Toledo
          • Cycling through the ancient narrow streets of Morella, Albarracín and Chinchón
          • Toasting the end of the ride with a glass of Port on the banks of the Douro
          Photo Highlights Dates
          Guided
          $250 OFF
          Guided
          Spain

          Basque Country to Andalucia Classic - North to South

          Guided Road Bike Tour

          Duration

          16 days

          Prices from

          $5,850 P.P.
          View Reviews
          21
          1
          2
          3
          4
          5
          Grade 4: Challenging
          More Info BOOK NOW

          Basque Country to Andalucia Classic - North to South

          Guided Road Bike Tour

          Start DateEnd DatePrice p.p.
          11/04/2027
          $250 OFF
          26/04/2027$5,850.00
          25/09/2027
          $250 OFF
          10/10/2027$5,850.00
          • Cycling through the varied beauty of 14 national parks
          • Delicious regional dishes which change from day to day as you traverse the entire country
          • Crossing the granite Guadarrama and Gredos mountain ranges as you move from the north to the south of the country
          • Views over the Straits of Gibraltar to Morocco
          • The beautiful towns of San Sebastian, Guadaloupe and Ronda
          • The satisfaction of arriving in to Tarifa with over 1,000 miles of Spanish roads having passed beneath your wheels
          Photo Highlights Dates
          Guided
          Guided
          France

          Provence - Le Ventoux a Velo

          Guided Road Bike Tour

          Duration

          8 days

          Prices from

          $3,850 P.P.
          View Reviews
          12
          1
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          4
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          Grade 3: Moderate
          More Info BOOK NOW

          Provence - Le Ventoux a Velo

          Guided Road Bike Tour

          Start DateEnd DatePrice p.p.
          12/06/202719/06/2027$3,850.00
          24/07/202731/07/2027$3,850.00
          • Exploring the world famous beauty of one of France’s most popular regions
          • Conquering Mont Ventoux – the mighty Géant de Provence
          • Stunning views of the turquoise waters of Lac de Sainte Croix
          • Riding the rim of the Gorge du Verdon, Europe’s very own Grand Canyon
          • The lavender fields of the Plateau de Valensole
          • Sipping on a cheeky post ride rosé in the sunshine
          Photo Highlights Dates
          Guided
          Guided
          Italy

          Lakes of Lombardia

          Guided Road Bike Tour

          Duration

          8 days

          Prices from

          $3,565 P.P.
          View Reviews
          20
          1
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          3
          4
          5
          Grade 3: Moderate
          More Info BOOK NOW

          Lakes of Lombardia

          Guided Road Bike Tour

          Start DateEnd DatePrice p.p.
          12/06/202719/06/2027$3,565.00
          10/07/202717/07/2027$3,565.00
          • Riding into Switzerland from Lake Maggiore to Lake Lugano
          • The ascent to Madonna del Ghisallo and the world famous cycling museum
          • Strolling through Bellagio on Lake Como after a great lake-side ride
          • Conquering Passo Maniva and the sweeping downhill to Lago di Idro
          • Relaxing with a post-ride drink overlooking yet another beautiful lake
          • Enjoying good food, fine wines and quality accommodation
          Photo Highlights Dates
          Self-Guided
          Self-Guided
          Italy

          Tuscany - Giro della Toscana

          Self-Guided Road Bike Tour

          Duration

          8 days

          Prices from

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

          Tuscany - Giro della Toscana

          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 in July and August)

          Season 1 – $2565 29 Mar – 14 Jun and 09 Sep – 26 Oct

          Season 2 – $2995 15 – 30 Jun and 01 – 08 Sep

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

          Season 1 – $2695 30 Mar – 14 Jun and 09 Sep – 26 Oct

          Season 2 – $3135 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.

          • Cycling through the historic wine regions of Tuscany, stopping off for a bit of wine tasting along the way
          • Staying in quality accommodation, with fantastically warm hospitality
          • Easing along the rolling hills of the ‘Colli Sienesi’
          • Riding the stunning UNESCO heritage region of Val d’Orcia
          • Stopping off at the lovely San Gimignano and Montalcino
          • Chilling out with a post-ride Chianti
          Photo Highlights Dates
          Guided
          Guided
          Italy

          Tuscany - Giro della Toscana

          Guided Road Bike Tour

          Duration

          8 days

          Prices from

          $2,995 P.P.
          View Reviews
          1
          1
          2
          3
          4
          5
          Grade 3: Moderate
          More Info BOOK NOW

          Tuscany - Giro della Toscana

          Guided Road Bike Tour

          Start DateEnd DatePrice p.p.
          03/10/2026
          Fully Booked
          10/10/2026$2,995.00
          01/05/202708/05/2027$3,135.00
          29/05/202705/06/2027$3,135.00
          02/10/2027
          Guaranteed
          09/10/2027$3,135.00
          • Cycling through the historic wine regions of Tuscany, stopping off for a bit of wine tasting along the way
          • Staying in quality accommodation, with fantastically warm hospitality
          • Easing along the rolling hills of the Colli Sienesi
          • Riding the stunning UNESCO heritage region of Val d’Orcia
          • Stopping off at the lovely San Gimignano and Montalcino
          • Chilling out with a post-ride Chianti
          Photo Highlights Dates
          Guided
          $200 OFF
          Guided
          Spain

          Bilbao to Barcelona

          Guided Road Bike Tour

          Duration

          10 days

          Prices from

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

          Bilbao to Barcelona

          Guided Road Bike Tour

          Start DateEnd DatePrice p.p.
          12/05/2027
          $200 OFF
          21/05/2027$4,280.00
          03/09/2027
          $200 OFF
          12/09/2027$4,280.00
          25/09/2027
          $200 OFF
          04/10/2027$4,280.00
          • An epic coast to coast adventure – riding all the way from the Atlantic to the Med under your own steam
          • Cycling with the impressive back-drop of the Pyrenees by your side
          • Dining each evening on rustic Spanish mountain cuisine
          • The striking pink granite of the Parc Natural de Montserrat
          • Dramatic castles, forts and monasteries perched on every hilltop
          • Seeing Barcelona stretched out in front of you, with the sea beyond
          Photo Highlights Dates
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          • 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
          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
          Quote
          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
          Quote
          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
          Quote
          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
          Quote
          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

          winter cycling in costa rica - two cyclists admiring the tropical view

          7 winter cycling destinations for sun-seekers

          The best winter cycling destinations provide a wonderful way to leave winter behind and discover new roads, cultures and landscapes on two wheels. Whether you're seeking winter sunshine, aiming to build fitness with some early-season training miles, or looking for an adventure to kick-start the year, there's plenty of winter cycling destinations offering warmer, sunnier ...

          David Hall - Road Cycling Product Specialist at Saddle Skedaddle
          David Hall
          October 2, 2026
          Cycling in Andalucia

          Sierras to the Coast: The best road cycling in Andalucia 

          If you’re looking for a top European cycling destination, then road cycling in Andalucia has to be up there with the best! Plus, with beautiful weather almost year-round, it’s the ideal destination for extending your cycling season. Head of Skedaddle España, Dan, has lived in this region for more than 25 years, guiding countless cycling ...

          Dan Hirst, Head of Skedaddle Espana
          Dan Hirst
          October 1, 2026
          Cycle route in Dumfries and Galloway

          Skedaddle guide to the best cycle routes in Dumfries and Galloway

          Dave Shuttle, UK Route Developer and Guide, talks us through our cycle routes in Dumfries and Galloway and why our newest leisure cycling holiday should be on your wish list for next year.   Over the years, Dave has guided and scouted multiple cycling routes in Scotland, so who better to give us a breakdown ...

          Dave Shuttle - UK Product Lead at Saddle Skedaddle
          Dave Shuttle
          September 21, 2026

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