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            Small Group Road Cycling Tours

            We found 41 Holidays in your search for:

            Destinations (72)
            Types of Cycling / Grades (1)
            Departure Month

            2025

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            Level of Support

            We found 41 Holidays in your search for:

            Select Order Order By
            Destinations (72)
            Types of Cycling / Grades (1)
            Departure Month

            2025

            2026

            2027

            Level of Support

            Join a peloton of like-minded riders on a small group tour with Skedaddle! Our group road cycling tours welcome everyone from solo travellers to groups of friends. You’ll love the fun and camaraderie as you ride along some of the world’s most beautiful roads.

            Our experienced guides and tour leaders are here to make sure every pedal stroke of your holiday runs like clockwork, plus you’ll have the back-up of a support vehicle to assist with mechanical issues and extra supplies. We’ll also arrange your luggage transfers and accommodation so all you need to worry about is focusing on tackling that next climb and taking in the gorgeous scenery as you ride. 

            • All Cycling Holidays
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            • SMALL GROUP CYCLING TOURS

            Page 2 of 5

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            Guided
            Guided
            Italy

            Tuscany - Giro della Toscana

            Guided Road Bike Tour

            Duration

            8 days

            Prices from

            $2,765 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.
            31/05/2025
            Guaranteed
            07/06/2025$2,765.00
            * 30/08/2025
            Last Spaces
            06/09/2025$2,765.00
            • 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

            $5,965 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.
            22/05/2025
            Contact Us
            07/06/2025$5,965.00
            25/09/2025
            Last Spaces
            11/10/2025$5,965.00
            21/05/202606/06/2026$6,265.00
            24/09/202610/10/2026$6,265.00
            • 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

            $7,595 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.
            * 23/08/202513/09/2025$7,595.00
            25/04/202616/05/2026$7,975.00
            29/08/202619/09/2026$7,975.00
            • 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

            Lakes of Lombardia

            Guided Road Bike Tour

            Duration

            8 days

            Prices from

            $3,250 P.P.
            View Reviews
            20
            1
            2
            3
            4
            5
            Grade 3: Moderate
            More Info BOOK NOW

            Lakes of Lombardia

            Guided Road Bike Tour

            Start DateEnd DatePrice p.p.
            * 12/07/2025
            Guaranteed
            19/07/2025$3,250.00
            * 02/08/202509/08/2025$3,250.00
            • 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

            $3,385 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.
            * 05/07/2025
            Guaranteed
            12/07/2025$3,385.00
            19/07/202526/07/2025$3,385.00
            • 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

            $3,525 P.P.
            View Reviews
            11
            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.
            18/10/2025
            Guaranteed
            25/10/2025$3,525.00
            • 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

            $3,795 P.P.
            View Reviews
            9
            1
            2
            3
            4
            5
            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$3,795.00
            • 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

            $2,955 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.
            * 08/06/202514/06/2025$2,955.00
            21/09/202527/09/2025$2,955.00
            • 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

            $2,910 P.P.
            View Reviews
            4
            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.
            26/10/202502/11/2025$2,910.00
            28/12/202504/01/2026$3,250.00
            • 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

            $4,190 P.P.
            View Reviews
            10
            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.
            * 18/05/2025
            Guaranteed
            27/05/2025$4,190.00
            04/09/2025
            Guaranteed
            13/09/2025$4,190.00
            18/09/202527/09/2025$4,190.00
            • 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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            Quote
            After over 40 tours with other operators, I was apprehensive about trying a new company, but have come away extremely pleased with Skedaddle!
            Bruce, Italy - Sardinian Mountains
            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
            Quite simply, there are not enough superlatives to describe how beautiful the Tuscan countryside and the accommodation chosen were!
            Robert, Italy - Tuscany Tourer
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