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          Grand Tour Inspired Cycling Tours

          We found 20 Holidays in your search for:

          Destinations (72)
          Types of Cycling / Grades (7)
          Departure Month

          2025

          2026

          2027

          Level of Support

          We found 20 Holidays in your search for:

          Select Order Order By
          Destinations (72)
          Types of Cycling / Grades (7)
          Departure Month

          2025

          2026

          2027

          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

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          Guided
          Guided
          Italy

          Grand Traverse Explorer - South to North

          Guided Road Bike Tour

          Duration

          22 days

          Prices from

          $7,850 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 Bike Tour

          Start DateEnd DatePrice p.p.
          25/04/202616/05/2026$7,850.00
          29/08/202619/09/2026$7,850.00
          • 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
          Italy

          Grand Traverse Classic - North to South

          Guided Road Bike Tour

          Duration

          17 days

          Prices from

          $5,995 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 Bike Tour

          Start DateEnd DatePrice p.p.
          21/05/202606/06/2026$5,995.00
          24/09/202610/10/2026$5,995.00
          • 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
          Spain

          Basque Country to Andalucia Explorer - North to South

          Guided Road Bike Tour

          Duration

          21 days

          Prices from

          $7,420 P.P.
          View Reviews
          1
          1
          2
          3
          4
          5
          Grade 3: Moderate
          More Info BOOK NOW

          Basque Country to Andalucia Explorer - North to South

          Guided Road Bike Tour

          SAVE ON 2026 ESCAPES

          Save $300 on this holiday when you book before 31 October 2025. Enter promo code BN26 when you book and your discount will be applied after your booking is confirmed. Ts and Cs apply.

          Start DateEnd DatePrice p.p.
          * 10/05/202630/05/2026$7,420.00
          * 30/08/202619/09/2026$7,420.00
          • 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
          Guided
          Spain

          Basque Country to Andalucia Classic - North to South

          Guided Road Bike Tour

          Duration

          16 days

          Prices from

          $5,905 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

          SAVE ON 2026 ESCAPES

          Save $250 on this holiday when you book before 31 October 2025. Enter promo code BN26 when you book and your discount will be applied after your booking is confirmed. Ts and Cs apply.

          Start DateEnd DatePrice p.p.
          * 10/04/202625/04/2026$5,905.00
          * 27/09/202612/10/2026$5,905.00
          • 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

          $3,810 P.P.
          View Reviews
          12
          1
          2
          3
          4
          5
          Grade 3: Moderate
          More Info BOOK NOW

          Provence - Le Ventoux a Velo

          Guided Road Bike Tour

          Start DateEnd DatePrice p.p.
          13/06/202620/06/2026$3,810.00
          08/08/202615/08/2026$3,810.00
          • 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.
          11/07/202618/07/2026$3,565.00
          01/08/202608/08/2026$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
          Guided
          Guided
          Italy

          Dolomiti Discoverer

          Guided Road Bike Tour

          Duration

          8 days

          Prices from

          $3,750 P.P.
          View Reviews
          2
          1
          2
          3
          4
          5
          Grade 3: Moderate
          More Info BOOK NOW

          Dolomiti Discoverer

          Guided Road Bike Tour

          Start DateEnd DatePrice p.p.
          04/07/202611/07/2026$3,750.00
          18/07/202625/07/2026$3,750.00
          • Admiring from various angles the classic grey and orange jagged peaks of the Dolomites
          • Riding the Sella Ronda, part of the Maratona delle Dolomiti, one of Italy’s biggest Gran Fondo events
          • Riding the dazzling descents and climbs you yearned to ride whilst watching the Giro d‘Italia
          • The sense of achievement at the end of the tour having conquered many climbs at your own pace.
          • Superb, mouth-watering and filling Italian food after a day on the bike – plenty of carbs!
          Photo Highlights Dates
          Self-Guided
          Self-Guided
          Italy

          Tuscany - Giro della Toscana

          Self-Guided Road Bike Tour

          Duration

          8 days

          Prices from

          $2,325 P.P.
          View Reviews
          4
          1
          2
          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.

          2025 24 Mar – 29 Oct (excluding dates throughout July and August)

          Season 1 – $2325 24 Mar – 16 Jun and 03 Sep – 29 Oct

          Season 2 – $2750 17 Jun – 30 Jun and 01 – 02 Sep

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

          Season 1 – $2425 29 Mar – 14 Jun and 09 Sep – 26 Oct

          Season 2 – $2895 15 Jun – 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

          $3,050 P.P.
          View Reviews
          3
          1
          2
          3
          4
          5
          Grade 3: Moderate
          More Info BOOK NOW

          Tuscany - Giro della Toscana

          Guided Road Bike Tour

          SAVE ON 2026 ESCAPES

          Save $125 on this holiday when you book before 31 October 2025. Enter promo code BN26 when you book and your discount will be applied after your booking is confirmed. Ts and Cs apply.

          Start DateEnd DatePrice p.p.
          * 02/05/202609/05/2026$3,050.00
          * 31/05/202607/06/2026$3,050.00
          * 29/08/202605/09/2026$3,050.00
          * 03/10/202610/10/2026$3,050.00
          • 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
          Guided
          Spain

          Bilbao to Barcelona

          Guided Road Bike Tour

          Duration

          10 days

          Prices from

          $4,210 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.
          06/05/2026
          Last Spaces
          15/05/2026$4,210.00
          03/09/202612/09/2026$4,210.00
          24/09/202603/10/2026$4,210.00
          • 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
          • Previous page
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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
          One of the very best trips! The kindness and professionalism of the lead guide and his locally based colleagues was outstanding in every respect.
          Brenda, Italy - Dolomites of Brenta, Guided Mountain Bike Holiday
          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
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          A quick guide to our two Scotland gravel tours...

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          Home to some of the most glorious scenery, outstanding history and cycling extravaganza...

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