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            Skedaddle Classics, Your Way

            Are you in search of a cycling tour that's specifically designed for you and your family or friends? Look no further than our exclusive collection of cycle tours, tailor-made to fulfill your dream cycling experience and shared only with those who matter most.

            To get you started, we've hand-picked some of our best-loved cycle tours, all set in destinations known like the back of our local teams' hands. With their vast local knowledge and expertise, we offer unparalleled flexibility to cater to your unique needs. From adjusting the number of cycling days to bike hire, support level, accommodation, and more – we can customize it all according to your preferences.

            Simply explore the tailor-made itineraries below, send us an enquiry mentioning your preferred trip and your priorities. Leave the rest to us, so you can sit back and savor the journey. Alternatively, visit our dedicated Tailor Made page to discover how we can turn your dream trip into a wonderful reality!

            • All Cycling Holidays
            • All Road Cycling Tours
            • Skedaddle Classics your way
            Select Order Order By
            Self-Guided
            Self-Guided
            Italy

            Tuscany - Giro della Toscana

            Self-Guided Road Bike Tour

            Duration

            8 days

            Prices from

            $2,205 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 – $2205 24 Mar – 16 Jun and 03 Sep – 29 Oct

            Season 2 – $2615 17 Jun – 30 Jun and 01 – 02 Sep

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

            Season 1 – $2300 29 Mar – 14 Jun and 09 Sep – 26 Oct

            Season 2 – $2750 15 Jun – 30 Jun and 01 – 08 Sep

            • 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

            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
            Self-Guided
            Self-Guided
            Spain

            Andalucia - Los Pueblos Blancos

            Self-Guided Road Bike Tour

            Duration

            8 days

            Prices from

            $2,030 P.P.
            View Reviews
            2
            1
            2
            3
            4
            5
            Grade 2 - 3: Gentle/Moderate
            More Info BOOK NOW

            Andalucia - Los Pueblos Blancos

            Self-Guided Road Bike Tour

            Daily departures available. The prices below are per person and are applicable for all start dates between and inclusive of the stated dates.

            2025 – $2030 – 01 Mar – 10 Apr / 20 Apr – 30 Apr / 12 May – 30 Jun / 09 Sep – 30 Nov

            2026 – $2085 – 01 Mar – 28 Mar / 05 Apr – 30 Apr / 03 May – 30 Jun / 08 Sep – 30 Nov

            • 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

            Roads of Ronda

            Guided Road Bike Tour

            Duration

            7 days

            Prices from

            $2,845 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.
            09/11/202515/11/2025$2,845.00
            • 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
            Self-Guided
            Self-Guided
            Spain

            Roads of Ronda

            Self-Guided Road Bike Tour

            Duration

            7 days

            Prices from

            $1,760 P.P.
            View Reviews
            1
            1
            2
            3
            4
            5
            Grade 3: Moderate
            More Info BOOK NOW

            Roads of Ronda

            Self-Guided Road Bike Tour

            Daily departures available. The prices below are per person and are applicable for all start dates between and inclusive of the stated dates.

            2025 – $1760 – 01 Mar – 10 Apr / 20 Apr – 30 Apr / 12 May – 30 Jun / 09 Sep – 30 Nov

            2026 – $1815 – 01 Mar – 28 Mar / 05 Apr – 30 Apr / 03 May – 30 Jun / 08 Sep – 30 Nov

            • Staying in the quintessentially Spanish town of Ronda
            • Cycling through the rugged, ‘bandit country’ of the Sierra de las Nieves
            • Reaching the top of the stunning Puerto de las Palomas
            • Tasty tapas and sunset sangrias
            • White villages (pueblos blancos) cut into the hillsides
            • Planning your own cycling days based on our route notes and recommendations
            Photo Highlights Dates
            Self-Guided
            Self-Guided
            Italy

            Sardinia - Coast to Coast

            Self-Guided Road Bike Tour

            Duration

            8 days

            Prices from

            $1,895 P.P.
            View Reviews
            3
            1
            2
            3
            4
            5
            Grade 2 - 3: Gentle/Moderate
            More Info BOOK NOW

            Sardinia - Coast to Coast

            Self-Guided Road Bike Tour

            Start DateEnd DatePrice p.p.
            29/09/202506/10/2025$1,895.00

            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 from 09 Jun – 31 Aug)

            Season 1 – $2070 24 Mar – 08 Jun / 09 Sep – 29 Oct

            Season 2 – $2275 01 Sept – 08 Sept

            Alternatively for a great value holiday select one of our scheduled departures below:

            • Riding the roller-coaster road below Mount Arcuentu to the west coast
            • Exploring the UNESCO heritage site of Su Nuraxi at Barumini
            • Taking a dip in the emerald waters of Sardinia
            • Cycling through the Sardinian “Blue Zone”
            • Dining on delicious home cooked food, washed down with tasty local wine!
            • The stunning descent to Bari Sardo on the East Coast
            Photo Highlights Dates
            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
            Next

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