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          Small Group Bike Tours & Trips

          We found 100 Holidays in your search for:

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

          2025

          2026

          2027

          Level of Support

          We found 100 Holidays in your search for:

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

          2025

          2026

          2027

          Level of Support

          Join a group of likeminded riders on a small group tour with Skedaddle! Whether you’re looking to join as a couple, group of friends, or as a solo traveller, you’ll feel part of one passionate pedallin’ community. Our tour leaders and guides will be on hand throughout your trip to ensure everything runs smoothly. You’ll also have a dedicated support vehicle to assist with everything from mechanical issues to emergency back-up and extra supplies.

          On a group tour, we take care of all your accommodation and luggage transfers. The only thing you’ll need to focus on is turning the pedals, enjoying the beautiful scenery and wondering what you’ll have for lunch (did we mention the legendary Skedaddle picnics?). It’s no wonder our small group tours are so popular!

          • All Cycling Holidays
          • SMALL GROUP CYCLING TOURS

          Page 2 of 10

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          Guided
          Guided
          Italy

          Tuscany - Giro della Toscana

          Guided Road Bike Tour

          Duration

          8 days

          Prices from

          $3,050 P.P.
          View Reviews
          3
          1
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          3
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          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
          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
          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

          Dolomiti Discoverer

          Guided Road Bike Tour

          Duration

          8 days

          Prices from

          $3,750 P.P.
          View Reviews
          2
          1
          2
          3
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          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
          Guided
          Guided
          Portugal

          Vineyards of the Douro Valley

          Guided Road Bike Tour

          Duration

          8 days

          Prices from

          $3,710 P.P.
          View Reviews
          11
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          Grade 3 - 4: Moderate/ Challenging
          More Info BOOK NOW

          Vineyards of the Douro Valley

          Guided Road Bike Tour

          SAVE ON 2026 ESCAPES

          Save $200 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.
          18/10/2025
          Fully Booked
          25/10/2025$3,710.00
          * 11/04/202618/04/2026$3,850.00
          * 17/10/202624/10/2026$3,850.00
          • Riding along the Douro river through immense vineyards surrounded by terraced slopes
          • Staying in the charming lodgings of wine farms, where we visit Port wine cellars and sample some port and wine
          • 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

          $3,995 P.P.
          View Reviews
          9
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          Grade 3: Moderate
          More Info BOOK NOW

          Atlantic Escape

          Guided Road Bike Tour

          Start DateEnd DatePrice p.p.
          01/11/2025
          Guaranteed
          10/11/2025$3,995.00
          25/04/202604/05/2026$4,135.00
          31/10/202609/11/2026$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
          Guided
          Guided
          Spain

          La Rioja - Ruta del Vino

          Guided Road Bike Tour

          Duration

          7 days

          Prices from

          $3,265 P.P.
          View Reviews
          8
          1
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          Grade 3: Moderate
          More Info BOOK NOW

          La Rioja - Ruta del Vino

          Guided Road Bike Tour

          Start DateEnd DatePrice p.p.
          14/06/202620/06/2026$3,265.00
          27/09/202603/10/2026$3,265.00
          • 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

          $3,065 P.P.
          View Reviews
          4
          1
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          Grade 2 - 3: Gentle/Moderate
          More Info BOOK NOW

          Andalucia - Los Pueblos Blancos

          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.
          26/10/202502/11/2025$3,065.00
          28/12/2025
          Guaranteed
          04/01/2026$3,425.00
          * 21/03/202628/03/2026$3,225.00
          * 25/10/202601/11/2026$3,225.00
          * 28/12/202604/01/2027$3,595.00
          • 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
          Guided
          Guided
          Spain

          Bilbao to Barcelona

          Guided Road Bike Tour

          Duration

          10 days

          Prices from

          $4,210 P.P.
          View Reviews
          2
          1
          2
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          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
          Guided
          Guided
          Spain

          Roads of Ronda

          Guided Road Bike Tour

          Duration

          7 days

          Prices from

          $2,995 P.P.
          View Reviews
          7
          1
          2
          3
          4
          5
          Grade 3: Moderate
          More Info BOOK NOW

          Roads of Ronda

          Guided Road Bike Tour

          Start DateEnd DatePrice p.p.
          09/11/2025
          Last Spaces
          15/11/2025$2,995.00
          08/03/202614/03/2026$3,135.00
          08/11/202614/11/2026$3,135.00
          • 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
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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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