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            Place to Place Journeys

            We found 45 Holidays in your search for:

            Destinations (82)
            Types of Cycling / Grades (1)
            Departure Month

            2026

            2027

            2028

            Level of Support

            We found 45 Holidays in your search for:

            Select Order Order By
            Destinations (82)
            Types of Cycling / Grades (1)
            Departure Month

            2026

            2027

            2028

            Level of Support

            Our place to place leisure cycling journeys are perfect for those those keen to tick off some of Europe’s cultural highlights, all whilst exploring a range of manageable cycling routes.

            Whether you’re riding from Pisa to Florence, Amsterdam to Bruges or Granada to Seville, all of our journeys offer a rewarding sense of achievement and plenty of cultural treasures en route. See our full range of place to place cycling tours below. 

            • All Cycling Holidays
            • All Leisure Cycling Holidays
            • Place To Place Journeys

            Page 3 of 5

            Select Order Order By
            Self-Guided
            Self-Guided
            Austria

            The Danube Cyclepath

            Self-Guided Leisure Cycling Holiday

            Duration

            8 days

            Prices from

            £1,295 P.P.
            View Reviews
            5
            1
            2
            3
            4
            5
            Grade 2: Gentle
            More Info BOOK NOW

            The Danube Cyclepath

            Self-Guided Leisure Cycling Holiday

            E-BIKE HIRE AVAILABLE

            This tour is well-suited to both regular bikes and pedal assist e-bikes, and you can choose to hire either when you book your tour with us. Confident cyclists will enjoy the boost from a battery for those cheeky climbs, and with less effort required on the bike, you’ll have more energy at the end of the day for off-the-bike activities.

            2026 – £1295 Daily departures available from 28 Mar – 11 Oct.

            • Starting your trip in the baroque town of Schärding
            • Cycling through Passau – the city of three rivers
            • Riding the famous Schlogen bend
            • Winding your way to Grein with its imposing castle
            • Enjoying the natural wonders of the Wachau
            • Soaking up the sights in Vienna
            Photo Highlights Dates
            Self-Guided
            Self-Guided
            United Kingdom

            Cotswolds to Windsor

            Self-Guided Leisure Cycling Holiday

            Duration

            5 days

            Prices from

            £1,095 P.P.
            View Reviews
            2
            1
            2
            3
            4
            5
            Grade 2-3: Gentle/Moderate
            More Info BOOK NOW

            Cotswolds to Windsor

            Self-Guided Leisure Cycling Holiday

            E-BIKE HIRE AVAILABLE

            This holiday is well-suited to both regular bikes and pedal assist e-bikes, and you can choose to hire either when you book your holiday with us. Confident cyclists will enjoy the boost from a battery for those cheeky climbs, and with less effort required on the bike, you’ll have more energy at the end of the day for off-the-bike activities.

            Daily departures available from April to mid October.

            Choose your own dates from:

            2026 £1095 per person

            For a group of 4 or more we can offer the reduced rate of £945.

            You either can make a booking online or over the phone. Once we have your details, we’ll be able to check availability.

            • Tracing the River Thames from near its source all the way to Windsor
            • Didcot and its impressive railway heritage
            • The impressive Uffington White Horse & Dragon Hill
            • Beautiful wooded hills and green landscapes of the Chilterns
            • World famous Windsor Castle
            • Traditional pubs and award-winning English wines at the home of the Royal Regatta
            Photo Highlights Dates
            Supported
            Supported
            United Kingdom

            Way of the Roses

            Supported Leisure Cycling Holiday

            Duration

            6 days

            Prices from

            £1,095 P.P.
            View Reviews
            3
            1
            2
            3
            4
            5
            Grade 3 : Moderate
            More Info BOOK NOW

            Way of the Roses

            Supported Leisure Cycling Holiday

            E-BIKE HIRE AVAILABLE

            This tour is well-suited to both regular bikes and pedal assist e-bikes, and you can choose to hire either when you book your tour with us. Confident cyclists will enjoy the boost from a battery for those cheeky climbs, and with less effort required on the bike, you’ll have more energy at the end of the day for off-the-bike activities. You may choose to hire an e-bike on a group or supported tour but bear in mind that the pace will be set to riders without an e-bike.

            Start DateEnd DatePrice p.p.
            14/06/2026
            Guaranteed
            19/06/2026£1,095.00
            30/08/202604/09/2026£1,095.00
            20/09/202625/09/2026£1,095.00
            25/04/202730/04/2027£1,125.00
            20/06/202725/06/2027£1,125.00
            29/08/202703/09/2027£1,125.00
            • Posing at Eric Morecambe’s statue on Morecambe seafront
            • Cycling through the Forest of Bowland & Yorkshire Dales
            • Superb local ales and tasty food every night
            • York – flat cycling, big Minster
            • The chalky rolling hills, with big country views of the Wolds
            • Fish & chips on Bridlington’s waterfront to celebrate your ride!
            Photo Highlights Dates
            Guided
            Guided
            Scotland

            Scotland - Hebridean Way

            Guided Leisure Cycling Holiday

            Duration

            7 days

            Prices from

            £2,555 P.P.
            View Reviews
            11
            1
            2
            3
            4
            5
            Grade 3-4 : Moderate/Active
            More Info BOOK NOW

            Scotland - Hebridean Way

            Guided Leisure Cycling Holiday

            LAST CHANCE OFFERS!

            Choose half-price bike hire or get 5% off tour departing 16 Aug 2026. Book before 01 June 2026 and enter promo code LETSGO26. Your discount will be applied once your booking is confirmed. Ts and Cs apply.

            Start DateEnd DatePrice p.p.
            24/05/2026
            Last Spaces
            30/05/2026£2,555.00
            31/05/2026
            Last Spaces
            06/06/2026£2,555.00
            21/06/2026
            Fully Booked
            27/06/2026£2,555.00
            05/07/2026
            Guaranteed
            11/07/2026£2,555.00
            26/07/2026
            Guaranteed
            01/08/2026£2,555.00
            * 16/08/2026
            Guaranteed
            22/08/2026£2,555.00
            30/08/2026
            Guaranteed
            05/09/2026£2,555.00
            02/05/202708/05/2027£2,635.00
            23/05/202729/05/2027£2,635.00
            06/06/202712/06/2027£2,635.00
            27/06/202703/07/2027£2,635.00
            08/08/202714/08/2027£2,635.00
            29/08/202704/09/2027£2,635.00
            12/09/202718/09/2027£2,635.00
            • Riding along the Golden Road
            • Miles and miles of picture-perfect white sand beaches
            • Enjoying a wee dram from the Distillery at Tarbert
            • Seeing the traditional weaving of Harris Tweed
            • Views of Luskentyre Beach over a delicious picnic lunch
            • Visiting the Blackhouse Village at Gearrannan
            • The awe inspiring Callanish Standing Stones
            Photo Highlights Dates
            Supported
            Supported
            United Kingdom

            Hadrian's Cycleway

            Supported Leisure cycling holiday

            Duration

            6 days

            Prices from

            £995 P.P.
            View Reviews
            15
            1
            2
            3
            4
            5
            Grade 3 : Moderate
            More Info BOOK NOW

            Hadrian's Cycleway

            Supported Leisure cycling holiday

            E-BIKE HIRE AVAILABLE

            This tour is well-suited to both regular bikes and pedal assist e-bikes, and you can choose to hire either when you book your tour with us. Confident cyclists will enjoy the boost from a battery for those cheeky climbs, and with less effort required on the bike, you’ll have more energy at the end of the day for off-the-bike activities. You may choose to hire an e-bike on a group or supported tour but bear in mind that the pace will be set to riders without an e-bike.

            Start DateEnd DatePrice p.p.
            17/07/2026
            Fully Booked
            22/07/2026£995.00
            18/09/2026
            Guaranteed
            23/09/2026£995.00
            25/06/202730/06/2027£1,025.00
            30/07/202704/08/2027£1,025.00
            • The well-preserved Hadrian’s Wall forts of Birdoswald and Vindolanda
            • The rugged beauty of the North Pennines
            • The picturesque market town of Corbridge
            • The view down the Tyne as you arrive into Newcastle
            • The sense of achievement having ridden from coast to coast
            • Following in the footsteps of the Roman Empire
            Photo Highlights Dates
            Self-Guided
            Self-Guided
            United Kingdom

            Way of the Roses (5 days cycling)

            Self-Guided Leisure Cycling Holiday

            Duration

            6 days

            Prices from

            £995 P.P.
            View Reviews
            13
            1
            2
            3
            4
            5
            Grade 3 : Moderate
            More Info BOOK NOW

            Way of the Roses (5 days cycling)

            Self-Guided Leisure Cycling Holiday

            E-BIKE HIRE AVAILABLE

            This tour is well-suited to both regular bikes and pedal assist e-bikes, and you can choose to hire either when you book your tour with us. Confident cyclists will enjoy the boost from a battery for those cheeky climbs, and with less effort required on the bike, you’ll have more energy at the end of the day for off-the-bike activities.  

            Start DateEnd DatePrice p.p.
            31/05/2026
            Guaranteed
            05/06/2026£995.00
            28/06/202603/07/2026£995.00
            02/08/202607/08/2026£995.00
            23/08/2026
            Guaranteed
            28/08/2026£995.00
            13/09/202618/09/2026£995.00

            Daily departures (excl. Thu and Fri) available from April to mid October.

            Choose your own dates from:

            2026 £1255 per person

            You either can make a booking online or over the phone. Once we have your details, we’ll be able to check availability.

            Alternatively for a great value holiday choose one of our scheduled weekend departures below.

            • Eric Morecambe’s statue on Morecambe waterfront
            • Cycling through the Forest of Bowland and the Yorkshire Dales
            • Yorkshire ales and great pub food
            • York – flat cycling, big Minster
            • The Wolds, chalky rolling hills, with big country views
            • Fish & chips on Bridlington’s waterfront to celebrate your achievement!
            Photo Highlights Dates
            Supported
            Supported
            Portugal

            Azure Ocean Ride

            Supported Leisure Cycling Holiday

            Duration

            8 days

            Prices from

            £1,995 P.P.
            1
            2
            3
            4
            5
            Grade 3 : Moderate
            More Info BOOK NOW

            Azure Ocean Ride

            Supported Leisure Cycling Holiday

            E-BIKE HIRE AVAILABLE

            This tour is well-suited to both regular bikes and pedal assist e-bikes, and you can choose to hire either when you book your tour with us. Confident cyclists will enjoy the boost from a battery for those cheeky climbs, and with less effort required on the bike, you’ll have more energy at the end of the day for off-the-bike activities. You may choose to hire an e-bike on a group or supported tour but bear in mind that the pace will be set to riders without an e-bike. 

            Start DateEnd DatePrice p.p.
            20/06/2026
            Guaranteed
            27/06/2026£1,995.00
            25/07/202601/08/2026£1,995.00
            03/10/2026
            Fully Booked
            10/10/2026£1,995.00
            • Discovering Portugal’s most beautiful beaches
            • Cycling alongside the Ria de Aviero, a 40km stretch of blue lagoon
            • Helping the fishermen with their catch in Praia da Vieira
            • Enjoying the views of the western shoreline from the Sitio viewpoint
            • Exploring the historical, castle walled village of Óbidos
            • Staying in beautiful Vimeiro
            Photo Highlights Dates
            Self-Guided
            Self-Guided
            Italy

            Lake Garda to Venice

            Self-Guided Leisure Cycling Holiday

            Duration

            8 days

            Prices from

            £1,865 P.P.
            View Reviews
            1
            1
            2
            3
            4
            5
            Grade 2: Gentle
            More Info BOOK NOW

            Lake Garda to Venice

            Self-Guided Leisure Cycling Holiday

            E-BIKE HIRE AVAILABLE

            This tour is well-suited to both regular bikes and pedal assist e-bikes, and you can choose to hire either when you book your tour with us. Confident cyclists will enjoy the boost from a battery for those cheeky climbs, and with less effort required on the bike, you’ll have more energy at the end of the day for off-the-bike activities.

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

            2026 18 Apr – 26 Oct (excluding dates throughout July and August)

            Season 1 – £1865 18 Apr – 14 Jun and 09 Sep – 26 Oct

            Season 2 – £2095 15 Jun – 30 Jun and 01 – 08 Sep

            If you‘re looking for a longer holiday, our Via Claudia route links into this tour perfectly; two self-guided tours of a similar grade that you‘re able to do back to back. Contact us if you’d like more info on this!

            To ensure you have the best experience possible, we’d recommend travelling in the Spring or in the Autumn. We don’t as standard offer this tour in the hotter, more humid, busier summer months of July and August. If however your dates are set in July or August, please call us for a chat and we’ll do what we can to accommodate you.

            • Enjoying a swim in Lake Garda
            • Absorbing the hidden Renaissance gems of the ‘belpaese’
            • Exploring Verona – a piece of art in itself
            • Discovering the medieval fortification of Montagnana
            • Taking a gondola ride along the canals of Venice
            • Cycling along Pellestrina Island surrounded by Venetian lagoons and fishing boats
            Photo Highlights Dates
            Self-Guided
            Self-Guided
            United Kingdom

            C2C - Coast to Coast (4 Days Cycling)

            Self-Guided Leisure Cycling Holiday

            Duration

            5 days

            Prices from

            £775 P.P.
            14
            1
            2
            3
            4
            5
            Grade 3 : Moderate
            More Info BOOK NOW

            C2C - Coast to Coast (4 Days Cycling)

            Self-Guided Leisure Cycling Holiday

            12/06/2026 (Newcastle)16/06/2026£775.00
            19/06/2026 (Newcastle)23/06/2026£775.00
            17/07/2026 (Newcastle)21/07/2026£775.00
            28/08/2026 (Newcastle)01/09/2026£775.00
            04/09/2026 (Penrith)08/09/2026£775.00

            Daily departures available from April to end of September. If you‘re interested in doing this holiday in October please call and chat to us.

            Choose your own dates from:

            2026 £915 per person

            Due to some big events happening in Newcastle in July and September, it’s not possible to start this tour in Newcastle between the 08th and 10th Jul, or the 10th and 14th Sep, but do chat to us if you have set dates, as we can likely organise a Penrith start for you.

            You can either make a booking online or over the phone. Once we have your details, we’ll be able to check availability.

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

            • UK’s favourite long distance cycle route
            • Dramatic English landscapes
            • Cycle friendly route
            • Stress-free cycling complimented with an abundance of pubs and cafes en route
            • Bike friendly B&Bs offering mouthwatering breakfasts
            • Flexibility to choose your own start date or one of our great value scheduled departure dates
            • Suitable for adults and older children
            Photo Highlights Dates
            Guided
            Guided
            Italy

            Tuscany to Rome

            Guided Electric Bike Holiday

            Duration

            8 days

            Prices from

            £2,395 P.P.
            View Reviews
            7
            1
            2
            3
            4
            5
            Grade 3 : Moderate
            More Info BOOK NOW

            Tuscany to Rome

            Guided Electric Bike Holiday

            LAST CHANCE OFFERS!

            Choose half-price bike hire or get 5% off tour departing 12 Sep 2026. Book before 01 June 2026 and enter promo code LETSGO26. Your discount will be applied once your booking is confirmed. Ts and Cs apply.

            Start DateEnd DatePrice p.p.
            23/05/2026
            Fully Booked
            30/05/2026£2,395.00
            * 12/09/202619/09/2026£2,395.00
            • Staying in Tuscan accommodation overlooking stunning landscapes
            • Discovering the amazing towns of Siena, San Quirico and Pienza
            • Sampling the best wines of Chianti, Montepulciano and Montalcino
            • Enjoying the journey from Tuscany to Rome on a variety of terrain, including ancient Roman roads
            • Exploring the lesser-known historical towns of Lazio, such as Sutri with it’s Roman amphitheatre
            • The sense of achievement riding into St Peter’s Square in Rome
            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
            What one pays for is not having to worry about anything – and Skedaddle does an excellent job taking care of us. We haven’t tried the other tour companies but why bother when Skedaddle is top notch.
            Roger, France - Chateaux of the Loire
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            The guides and other group members really made the holiday enjoyable. Our guide was friendly, professional and knowledgeable.
            Elaine, Italy - Tuscany to Rome
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            All the services we received were first class. This was a real holiday and going with Skedaddle took all the stress of booking accommodation from home, route planning and so on, so all we had to do was enjoy the cycling. This has been one of the best holidays in my life.
            Alison, Italy - Sardinia Island Flavours
            Quote
            What do you like most about Skedaddle? Where do I start? The booking process, the hotels, the guides, the lunches, the places they go, the people I meet, the pit stops, the Skedaddle community, reliability, I can put my trust in them to provide a great and memorable experience.
            David, Austria & Italy - La Via Claudia
            Quote
            Skedaddle holidays are always great; you can ride your bike and they pretty much do the rest! Being able to use two wheels as a mode of transport to travel across the country, supported by Skedaddle, just shows the beauty, and power, of bikes. Thank you for making it possible!
            Kate, UK - C2C
            Quote
            We just LOVED the whole thing – route, weather, food, scenery, being outside – it was probably one of the best holidays we have had.
            Inese, Austria - The Danube Cyclepath
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