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          2027 Road Cycling Tours To Book Now

          We found 21 Holidays in your search for:

          Destinations (75)
          Types of Cycling / Grades (1)
          Departure Month

          2026

          2027

          2028

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          We found 21 Holidays in your search for:

          Select Order Order By
          Destinations (75)
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          2027 Road Cycling Tours 2027 Adventure Cycling Tours

          Planning ahead for your dream cycling tour? Whether you're training to complete the UK's ultimate challenge ride - Land's End to John o' Groats - or searching for your trip of a lifetime exploring a far-flung destination, we know it’s helpful to plan ahead. These tours all have 2027 dates available to book now. Plus, you’ll only need to pay a deposit upfront to secure your space.

          What are you waiting for? Stop dreaming and start planning!

          • All Cycling Holidays
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          Page 2 of 3

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          Guided
          Guided
          Costa Rica

          Ruta de los Volcanes

          Guided Road Bike Tour

          Duration

          13 days

          Prices from

          $6,280 P.P.
          View Reviews
          13
          1
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          3
          4
          5
          Grade 3: Moderate
          More Info BOOK NOW

          Ruta de los Volcanes

          Guided Road Bike Tour

          Start DateEnd DatePrice p.p.
          22/12/202603/01/2027$6,280.00
          13/03/202725/03/2027$6,320.00
          22/12/202703/01/2028$6,465.00
          • Spotting an unparalleled diversity of wildlife
          • Cycling in the shadow of palm trees along the Pacific coast
          • Breaking through the clouds as we cross Costa Rica’s central mountains
          • Enjoying volcanic vistas over a drink in La Fortuna
          • Watching the sun go down from Samara beach after a rewarding day in the saddle
          • The change in scenery on opposing sides of the continental divide
          Photo Highlights Dates
          Guided
          $150 OFF
          Guided
          France

          Alps - Mont Ventoux to Alpe d'Huez

          Guided Road Bike Tour

          Duration

          8 days

          Prices from

          $3,850 P.P.
          View Reviews
          8
          1
          2
          3
          4
          5
          Grade 4: Challenging
          More Info BOOK NOW

          Alps - Mont Ventoux to Alpe d'Huez

          Guided Road Bike Tour

          Start DateEnd DatePrice p.p.
          26/06/2027
          $150 OFF
          Guaranteed
          03/07/2027$3,850.00
          24/07/2027
          $150 OFF
          31/07/2027$3,850.00
          • Legendary Tour de France challenges every day
          • ‘Warming up’ on Mont Ventoux, the ‘Giant of Provence’
          • Blue skies, fresh air and snow-capped peaks
          • ‘Top of the world’ sensations on the summit of the Izoard
          • Ticking off lots of Tour de France classics
          • Riding through Provençal lavender flelds, synonymous with the region
          • The final challenge of the legendary Alpe d‘Huez
          Photo Highlights Dates
          Guided
          $200 OFF
          Guided
          Italy

          Alps and Dolomites - Giants of the Giro

          Guided Road Bike Tour

          Duration

          9 days

          Prices from

          $3,710 P.P.
          View Reviews
          18
          1
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          3
          4
          5
          Grade 4 - 5
          More Info BOOK NOW

          Alps and Dolomites - Giants of the Giro

          Guided Road Bike Tour

          Start DateEnd DatePrice p.p.
          17/07/2027
          $200 OFF
          25/07/2027$3,710.00
          21/08/2027
          $200 OFF
          29/08/2027$3,710.00
          • Cycling through the best alpine and dolomite scenery of Italy
          • Climbing the iconic Mortirolo, Passo Gavia and Passo Stelvio of Giro d’Italia fame
          • Enjoying post-ride relaxation in typical chalet-style mountain hotels
          • Re-charging your energy levels every evening with tasty local fayre
          • Testing your legs and endurance on the final Monte Grappa climb
          • Enjoying an aperitif in the lively towns of San Pellegrino Terme, Bormio and Bassano del Grappa
          Photo Highlights Dates
          Guided
          $400 OFF
          Guided
          Spain & Portugal

          Trans Iberia - Barcelona to Porto

          Guided Road Bike Tour

          Duration

          22 days

          Prices from

          $8,935 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.
          09/04/2027
          $400 OFF
          30/04/2027$8,935.00
          05/10/2027
          $400 OFF
          26/10/2027$8,935.00
          • 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
          $125 OFF
          Guided
          Morocco

          Road Atlas

          Guided Road Bike Tour

          Duration

          10 days

          Prices from

          $2,710 P.P.
          View Reviews
          30
          1
          2
          3
          4
          5
          Grade 3: Moderate
          More Info BOOK NOW

          Road Atlas

          Guided Road Bike Tour

          Start DateEnd DatePrice p.p.
          07/11/2026
          Fully Booked
          16/11/2026$2,710.00
          27/12/202605/01/2027$2,710.00
          30/01/2027
          Guaranteed
          08/02/2027$2,850.00
          06/11/2027
          $125 OFF
          15/11/2027$2,850.00
          27/12/2027
          $125 OFF
          05/01/2028$2,850.00
          • The High Atlas mountain range
          • The outstanding Ounila Valley and Ait Benhaddou Kasbah
          • Exploring the surreal blue rocks of Tafraoute
          • The incredible 100km ride from Tafraoute towards the coast
          • Enjoying a cold beer on one of Morocco’s finest terraces at Immouzer
          • The sights, smells and sounds of the Marrakech souk
          • Starting and finishing in this years ‘Capital of Culture’ Marrakech
          Photo Highlights Dates
          Guided
          $125 OFF
          Guided
          Italy

          Coast to Coast - Puglia to Cilento

          Guided Road Bike Tour

          Duration

          8 days

          Prices from

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

          Coast to Coast - Puglia to Cilento

          Guided Road Bike Tour

          Start DateEnd DatePrice p.p.
          17/04/2027
          $125 OFF
          24/04/2027$3,135.00
          25/04/2027
          $125 OFF
          02/05/2027$3,135.00
          26/09/2027
          $125 OFF
          03/10/2027$3,135.00
          • An epic coast to coast journey through southern Italy riding from the Adriatic coast to the Tyrrhenian Sea
          • Exploring the UNESCO World Heritage sites of Alberobello, Matera, Padula and Paestum
          • Losing ourselves in the labyrinthic white washed alleyways of Noci and Tricarico
          • Climbing the hills of little-known Basilicata, to the hill-top villages of Castelmezzano, Calvello and Marsico Vetere
          • Cycling through the Dolomiti Lucane, southern Italy’s lesser-known Dolomites
          • Enjoying the roller-coaster ride along the Cilento Coast from Palinuro to Paestum
          • Sampling southern Italy’s best food and wine
          Photo Highlights Dates
          Guided
          $400 OFF
          Guided
          Czech Republic, Austria, Slovenia & Italy

          Prague to Venice

          Guided Road Bike Tour

          Duration

          21 days

          Prices from

          $8,850 P.P.
          View Reviews
          5
          1
          2
          3
          4
          5
          Grade 3: Moderate
          More Info BOOK NOW

          Prague to Venice

          Guided Road Bike Tour

          Start DateEnd DatePrice p.p.
          05/06/2027
          Last Spaces
          25/06/2027$8,850.00
          03/07/2027
          $400 OFF
          23/07/2027$8,850.00
          31/07/2027
          $400 OFF
          20/08/2027$8,850.00
          • A journey from Central Europe to the Mediterranean through four European countries
          • Visit the vibrant capitals of Prague, Vienna and Ljubljana
          • Learn about the historical Central European regions of Bohemia and Styria
          • Explore the UNESCO World Heritage sites of Prague, Cesky Krumlov, Vienna, Graz, and Venice
          • Have a well deserved end-of-ride pilsner seated in the village square of a little Bohemian village
          • Enjoy quiet countryside roads with sweeping views all the way from Prague to Venice
          • Staying in quality accommodation, with warm traditional hospitality
          • Feast on the traditional dishes, desserts and drinks of the Czech, Austrian and Slovenian cuisine.
          Photo Highlights Dates
          Guided
          Guided
          Colombia

          Emerald Mountains

          Guided Road Bike Tour

          Duration

          13 days

          Prices from

          $5,995 P.P.
          View Reviews
          27
          1
          2
          3
          4
          5
          Grade 4: Challenging
          More Info BOOK NOW

          Emerald Mountains

          Guided Road Bike Tour

          Start DateEnd DatePrice p.p.
          16/01/2027
          Guaranteed
          28/01/2027$5,995.00
          06/02/2027
          Guaranteed
          18/02/2027$5,995.00
          15/01/202827/01/2028$6,280.00
          05/02/202817/02/2028$6,280.00
          • Exploring unspoiled Andean highlands
          • The historic city of Cartagena
          • The hospitality of locals, so proud to show off their country
          • The challenges offered by Colombia’s dramatic mountains
          • Cycling with the warm Caribbean breeze at your back
          • Being amongst the first to ride in this emerging destination
          Photo Highlights Dates
          Guided
          $300 OFF
          Guided
          Italy

          Grand Traverse Explorer - South to North

          Guided Road Bike Tour

          Duration

          22 days

          Prices from

          $8,080 P.P.
          View Reviews
          6
          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.
          24/04/2027
          $300 OFF
          15/05/2027$8,080.00
          28/08/2027
          $300 OFF
          18/09/2027$8,080.00
          • 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
          $250 OFF
          Guided
          Spain

          Basque Country to Andalucia Classic - North to South

          Guided Road Bike Tour

          Duration

          16 days

          Prices from

          $6,135 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$6,135.00
          25/09/2027
          $250 OFF
          10/10/2027$6,135.00
          • 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
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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
          100% perfection from Saddle Skedaddle on a recent road tour. Amazing route, exceptional accommodation, brilliant guides, quality hire bikes.....11 out of 10!
          Andy - Puglia to Cilento
          Quote
          All queries were replied almost immediately! Well done, Skedaddle, you have provided good consultant, good tour leader and good technical assistant.
          Sin Siew Tag, UK - Land's End to John O'Groats
          Quote
          This trip had something for everybody! The crew were fantastic, they were a vital part of the trip. The rest was the magic of Italy.
          Nigel, Italy - Grand Traverse
          Quote
          A fantastic journey of a lifetime led by excellent guides. Loved the Gorge du Verdon - tremendous climb and stupendous view.
          Miles, France - St Malo to Nice
          Quote
          I was the least experienced in the group - but was made to feel very comfortable and given lots of instruction and help.
          Catharine, France - Le Ventoux a Velo
          Quote
          The trip was amazing and exceeded my expectations. The route was spectacular and well thought, a perfect mix of challenges and easier days to cater for different abilities, levels of fitness and recovery times, without ever being boring.
          Lisa - Colombia Emerald Mountains
          Next

          News, Reviews & Stories

          Cyclists riding in Sweden on the Coastal Kattegattleden cycle route

          6 Reasons To Cycle In Sweden

          Our holidays in Sweden are some of the most popular in our leisure cycling range. We're excited to introduce a brand new guided group holiday for 2027 cycling the Kattegattleden, Sweden's first national cycle path. Read on to learn more about our tours and six reasons why you'll love cycling in Sweden. Coastal Kattegattleden The 8-day ...

          Paul Snedker
          Paul Snedker
          October 15, 2026
          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

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