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            Place to Place Journeys

            We found 85 Holidays in your search for:

            Destinations (82)
            Types of Cycling / Grades (7)
            Departure Month

            2025

            2026

            2027

            Level of Support

            We found 85 Holidays in your search for:

            Select Order Order By
            Destinations (82)
            Types of Cycling / Grades (7)
            Departure Month

            2025

            2026

            2027

            Level of Support

            There’s something immensely satisfying about cycling from one place to another; that feeling of escaping, of setting off on a journey of discovery and adventure. Pedallin’ from coast to coast, through mountain valleys, or alongside rivers, we’ve got a selection of place to place journeys for riders of all fitness levels and experience. We’ll take care of the complex logistics that go with planning a place to place tour - crafting the best routes, finding quality accommodation, arranging luggage transfers and bike hire - so you can simply enjoy the ride.

            • All Cycling Holidays
            • Place To Place Journeys

            Page 6 of 9

            Select Order Order By
            Guided
            Guided
            Spain

            Basque Country to Andalucia Classic - North to South

            Guided Road Cycling Holiday

            Duration

            16 days

            Prices from

            £4,135 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 Cycling Holiday

            SAVE ON 2026 ESCAPES

            Save £200 on this holiday when you book before 10 November 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£4,135.00
            * 27/09/202612/10/2026£4,135.00
            • 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
            Guided
            Guided
            Italy

            Grand Traverse Explorer - South to North

            Guided Road Cycling Holiday

            Duration

            22 days

            Prices from

            £5,495 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 Cycling Holiday

            Start DateEnd DatePrice p.p.
            25/04/202616/05/2026£5,495.00
            29/08/2026
            Guaranteed
            19/09/2026£5,495.00
            • 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
            Portugal

            Atlantic Escape

            Guided Road Cycling Holiday

            Duration

            10 days

            Prices from

            £2,795 P.P.
            View Reviews
            9
            1
            2
            3
            4
            5
            Grade 3 : Moderate
            More Info BOOK NOW

            Atlantic Escape

            Guided Road Cycling Holiday

            Start DateEnd DatePrice p.p.
            01/11/2025
            Guaranteed
            10/11/2025£2,795.00
            25/04/202604/05/2026£2,895.00
            31/10/202609/11/2026£2,895.00
            • 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
            Italy

            Coast to Coast - L'Adriatico al Tirreno

            Guided Road Cycling Holiday

            Duration

            9 days

            Prices from

            £2,695 P.P.
            View Reviews
            10
            1
            2
            3
            4
            5
            Grade 3 : Moderate
            More Info BOOK NOW

            Coast to Coast - L'Adriatico al Tirreno

            Guided Road Cycling Holiday

            SAVE ON 2026 ESCAPES

            Save £100 on this holiday when you book before 10 November 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.
            * 16/05/202624/05/2026£2,695.00
            * 12/09/202620/09/2026£2,695.00
            • An epic coast to coast journey riding all the way from the Adriatic coast to the Tyrrhenian Sea
            • Cycling through the smallest republic in Europe, San Marino
            • Easing along the rolling Nove Colli hills, the routes of the famous Italian Gran Fondo
            • Visiting historical sites such as the Palazzo Ducale in Orvieto and San Francis Abbey in Assisi
            • Staying in quality accommodation, with fantastically warm hospitality
            • Riding to Gubbio and Assisi, UNESCO World Heritage sites
            Photo Highlights Dates
            Supported
            Supported
            United Kingdom

            C2C - Coast to Coast

            Supported Leisure cycling holiday

            Duration

            5 days

            Prices from

            £895 P.P.
            View Reviews
            5
            1
            2
            3
            4
            5
            Grade 3-4 : Moderate/Active
            More Info BOOK NOW

            C2C - Coast to Coast

            Supported Leisure cycling holiday

            SAVE ON 2026 ESCAPES

            Save £50 on this holiday when you book before 10 November 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.
            * 08/05/202612/05/2026£895.00
            * 26/06/202630/06/2026£895.00
            * 07/08/202611/08/2026£895.00
            * 25/09/202629/09/2026£895.00
            • UK’s favourite long distance cycle route
            • Dramatic landscapes of the Lake District and Pennines
            • Cycle friendly route – cycle paths and quiet country lanes
            • Fully supported and awesome Skedaddle lunches
            • Bike friendly B&Bs offering mouthwatering breakfasts
            • Great sense of achievement, crossing the country, coast to coast
            Photo Highlights Dates
            Guided
            Guided
            Spain

            Bilbao to Santiago

            Guided Road Cycling Holiday

            Duration

            11 days

            Prices from

            £3,225 P.P.
            View Reviews
            4
            1
            2
            3
            4
            5
            Grade 3 : Moderate
            More Info BOOK NOW

            Bilbao to Santiago

            Guided Road Cycling Holiday

            Start DateEnd DatePrice p.p.
            28/06/202608/07/2026£3,225.00
            07/09/2026
            Last Spaces
            17/09/2026£3,225.00
            • Riding along the stunning and dramatic Cantabrian coastline
            • Enjoying a fabulous seafood platter in San Vicente de Barquera
            • Pouring cider in the old town of Oviedo
            • Arriving at the roof of the ‘Camino Primitivo‘, Puerto Palo
            • Cycling through beautiful, rural, enchanting Galicia to arrive in historical Santiago to collect a pilgrims’ certificate
            • The arrival at ‘the end of the world’ and awesome Cape Finisterre
            Photo Highlights Dates
            Guided
            Guided
            Sri Lanka

            Backroads and Beaches

            Guided Cycling Holiday

            Duration

            15 days

            Prices from

            £2,695 P.P.
            View Reviews
            17
            1
            2
            3
            4
            5
            Grade 3 : Moderate
            More Info BOOK NOW

            Backroads and Beaches

            Guided Cycling Holiday

            Start DateEnd DatePrice p.p.
            08/11/2025
            Fully Booked
            22/11/2025£2,695.00
            10/01/2026
            Last Spaces
            24/01/2026£2,895.00
            14/02/2026
            Fully Booked
            28/02/2026£2,895.00
            07/11/202621/11/2026£2,895.00
            13/02/202727/02/2027£2,895.00
            06/11/202720/11/2027£2,895.00
            • Eying up the elephants at Udawalawe
            • Stunning Sigirya and the Lion Rock
            • Colonial cool in Nuwara Eliya
            • Coastal cycling and beautiful beaches
            • Honing in on Horton Plains after a day in the hills
            • The Knuckles and Kandy’s Temple of the Tooth
            Photo Highlights Dates
            Guided
            Guided
            Scotland

            Scotland - Kirkpatrick Coast to Coast

            Guided Road Cycling Holiday

            Duration

            6 days

            Prices from

            £1,325 P.P.
            View Reviews
            4
            1
            2
            3
            4
            5
            Grade 3 : Moderate
            More Info BOOK NOW

            Scotland - Kirkpatrick Coast to Coast

            Guided Road Cycling Holiday

            Start DateEnd DatePrice p.p.
            10/05/202615/05/2026£1,325.00
            19/07/202624/07/2026£1,325.00
            13/09/202618/09/2026£1,325.00
            • Learn about Kirkpatrick Macmillan and his velocipede, which changed the world forever!
            • Breathtaking landscapes and dramatic coastlines
            • Charming and vibrant Kirkcudbright
            • Victorian viaducts and romantic ruined abbeys
            • Picturesque finish at the harbour of Eyemouth
            • Quiet country roads of the unexplored Borders
            Photo Highlights Dates
            Guided
            Guided
            Japan

            Fuji to Kyoto

            Guided Cycling Holiday

            Duration

            12 days

            Prices from

            £5,135 P.P.
            View Reviews
            2
            1
            2
            3
            4
            5
            Grade 3 : Moderate
            More Info BOOK NOW

            Fuji to Kyoto

            Guided Cycling Holiday

            Start DateEnd DatePrice p.p.
            09/11/2025
            Fully Booked
            20/11/2025£5,135.00
            23/11/2025
            Fully Booked
            04/12/2025£5,135.00
            12/04/2026
            Guaranteed
            23/04/2026£5,495.00
            08/11/202619/11/2026£5,595.00
            • Majestic Mt. Fuji and lovely Lake Kawaguchi
            • Exploring Nagahama and the awesome Hikone Castle
            • Hatage Onsen and its soothing effects after a day’s cycling
            • Bullet Trains and Bento boxes
            • Taking in colourful Kyoto
            • Peaceful pedalling and rural riding
            Photo Highlights Dates
            Guided
            Guided
            Spain

            Ruta de la Plata - Seville to Santiago

            Guided Gravel Riding Holiday

            Duration

            16 days

            Prices from

            £4,595 P.P.
            1
            2
            3
            4
            5
            Grade 3-4 : Moderate/Challenging
            More Info BOOK NOW

            Ruta de la Plata - Seville to Santiago

            Guided Gravel Riding Holiday

            SAVE ON 2026 ESCAPES

            Save £200 on this holiday when you book before 10 November 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.
            * 26/04/2026
            Guaranteed
            11/05/2026£4,595.00
            * 04/10/202619/10/2026£4,595.00
            • Biking through 4 diverse regions and 7 provinces of Spain
            • Delicious, regional cuisine
            • Sampling a diverse range of trails and paths
            • Exploring historic Roman roads and viaducts
            • 1,000km of challenging linear riding through ever changing landscapes
            • Crossing high passes and endless thrilling descents
            • Arriving in the beautiful Santiago de Compostela at the end of our journey
            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
            Next

            News, Reviews & Stories

            Gravel Riding in Veneto

            An interview with Lieven about what makes Veneto such a great gravel destination

            North York Moors - A Cycling Holiday To Remember

            We caught up with Dominic, Cycling Development Manager at North York Moors National Park on what makes this cycling route special.

            Gravel Riding in Scotland

            A quick guide to our two Scotland gravel tours...

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