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            2027 Cycling Holidays You Can Book Now

            We found 87 Holidays in your search for:

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

            2026

            2027

            2028

            Level of Support

            We found 87 Holidays in your search for:

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

            2026

            2027

            2028

            Level of Support
            2027 Road Cycling Holidays 2027 Adventure Cycling Holidays 2027 Leisure Cycling Holidays 2027 Mountain Bike Holidays

            Planning ahead for your dream cycling holiday? 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 in 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
            • BOOK EARLY

            Page 3 of 9

            Select Order Order By
            Self-Guided
            Self-Guided
            Scotland

            Scotland - Lochs and Glens

            Self-Guided Leisure Cycling Holiday

            Duration

            5 days

            Prices from

            £715 P.P.
            View Reviews
            6
            1
            2
            3
            4
            5
            Grade 3 : Moderate
            More Info BOOK NOW

            Scotland - Lochs and Glens

            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 from April to mid October.

            Choose your own dates from:

            2026 £715 per person

            2027 £730 per person

            Please note, due to some events happening in Killin in early-June, availability is very limited. Please chat to us if you’re looking to travel around this time and we’ll do our best to accommodate you.

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

            • Watching the sun burn away the mists from Loch Lomond
            • The beautiful lochs of Venachar, Lubnaig and Tay.
            • Enjoying a dram at one of Scotland’s whisky distilleries
            • Perth’s Georgian buildings
            • Miles of quiet winding loch-side roads
            • The spectacular mountain backdrop
            Photo Highlights Dates
            Guided
            Guided
            France

            Provence - Le Ventoux a Velo

            Guided Road Cycling Holiday

            Duration

            8 days

            Prices from

            £2,595 P.P.
            View Reviews
            12
            1
            2
            3
            4
            5
            Grade 3 : Moderate
            More Info BOOK NOW

            Provence - Le Ventoux a Velo

            Guided Road Cycling Holiday

            Start DateEnd DatePrice p.p.
            13/06/2026
            Guaranteed
            20/06/2026£2,595.00
            08/08/2026
            Contact Us
            15/08/2026£2,595.00
            12/06/202719/06/2027£2,695.00
            24/07/202731/07/2027£2,695.00
            • Exploring the world famous beauty of one of France’s most popular regions
            • Conquering Mont Ventoux – the mighty Géant de Provence
            • Stunning views of the turquoise waters of Lac de Sainte Croix
            • Riding the rim of the Gorge du Verdon, Europe’s very own Grand Canyon
            • The lavender fields of the Plateau de Valensole
            • Sipping on a cheeky post ride rosé in the sunshine
            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
            Guided
            Guided
            Italy

            Sardinia - Coastal Explorer

            Guided Road Cycling Holiday

            Duration

            8 days

            Prices from

            £2,125 P.P.
            View Reviews
            7
            1
            2
            3
            4
            5
            Grade 2 - 3: Gentle to Moderate
            More Info BOOK NOW

            Sardinia - Coastal Explorer

            Guided Road Cycling Holiday

            Start DateEnd DatePrice p.p.
            19/09/2026
            Guaranteed
            26/09/2026£2,125.00
            10/10/202617/10/2026£2,125.00
            08/05/202715/05/2027£2,225.00
            22/05/202729/05/2027£2,225.00
            18/09/202725/09/2027£2,225.00
            09/10/202716/10/2027£2,225.00
            • Riding the stunning coastal road from Alghero to Bosa
            • The ride to Montiferru through its oak forest
            • Sampling delightful Sardinian foods with a vast variety of local wines
            • Enjoying the view of Pan di Zucchero on the Nebida coastal ride
            • Sweeping down the long descent to Fluminimaggiore and Masua
            • Glimpsing the white beaches which hug the south west coast road
            Photo Highlights Dates
            Self-Guided
            Self-Guided
            United Kingdom

            Hadrian's Cycleway (3 days cycling)

            Self-Guided Leisure Cycling Holiday

            Duration

            4 days

            Prices from

            £495 P.P.
            View Reviews
            5
            1
            2
            3
            4
            5
            Grade 3 : Moderate
            More Info BOOK NOW

            Hadrian's Cycleway (3 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.
            24/07/2026
            Guaranteed
            27/07/2026£495.00
            07/08/202610/08/2026£495.00

            Daily departures available from April to mid October.

            Choose your own dates from:

            2026 £615 per person

            2027 £630 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.

            • The sense of achievement having ridden from coast to coast
            • The well preserved forts of Birdoswald and Vindolanda
            • The rugged beauty of the North Pennines
            • The picturesque market town of Corbridge
            • Following in the footsteps of the Roman Empire
            • Flexibility to choose your own start date or one of our great value scheduled departure dates
            Photo Highlights Dates
            Guided
            Guided
            Austria & Italy

            La Via Claudia

            Guided Leisure Cycling Holiday

            Duration

            8 days

            Prices from

            £2,495 P.P.
            View Reviews
            26
            1
            2
            3
            4
            5
            Grade 3-4 : Moderate/Active
            More Info BOOK NOW

            La Via Claudia

            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. 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£2,495.00
            18/07/2026
            Fully Booked
            25/07/2026£2,495.00
            22/08/2026
            Guaranteed
            29/08/2026£2,495.00
            19/06/202726/06/2027£2,595.00
            03/07/202710/07/2027£2,595.00
            21/08/202728/08/2027£2,595.00
            • Waking up to beautiful views of the Zugspitze, Germany’s highest peak
            • Cycling beside the vivid blue waters of the River Inn
            • Absorbing the history of an ancient trade route by bike
            • Exploring Merano – The Jewel of South Tyrol
            • Winding your way through the lovely Vinschgau Valley
            • A post-ride, tasty gelato on the shores of Lake Garda
            Photo Highlights Dates
            Guided
            Guided
            France

            Trans Pyrenees Challenge

            Guided Road Cycling Holiday

            Duration

            10 days

            Prices from

            £3,245 P.P.
            View Reviews
            8
            1
            2
            3
            4
            5
            Grade 4 : Challenging
            More Info BOOK NOW

            Trans Pyrenees Challenge

            Guided Road Cycling Holiday

            LAST CHANCE OFFERS!

            Choose half-price bike hire or get 5% off tour departing 02 Jul 2026. Book before 15 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.
            * 02/07/2026
            Guaranteed
            11/07/2026£3,245.00
            20/08/2026
            Contact Us
            29/08/2026£3,245.00
            01/07/202710/07/2027£3,395.00
            19/08/202728/08/2027£3,395.00
            • Riding the entire length of Europe’s most dramatic mountain range
            • Looking down on the switchbacks ahead from the summits of the Aspin and the Port de Pailhères
            • The breath-taking descent from the top of the Tourmalet
            • Fresh crepes and a coffee at the summit of Col de Peyresourde
            • Bathing tired legs in the outdoor thermal waters in Ax-les-Thermes
            • Fine Spanish food and wine in Bossost
            • A picnic and celebratory drinks on the beach by the Med
            Photo Highlights Dates
            Guided
            Guided
            Scotland

            Scotland - Tour d'Ecosse

            Guided Road Cycling Holiday

            Duration

            8 days

            Prices from

            £1,855 P.P.
            View Reviews
            6
            1
            2
            3
            4
            5
            Grade 3 : Moderate
            More Info BOOK NOW

            Scotland - Tour d'Ecosse

            Guided Road Cycling Holiday

            Start DateEnd DatePrice p.p.
            13/06/2026
            Fully Booked
            20/06/2026£1,855.00
            04/07/2026
            Last Spaces
            11/07/2026£1,855.00
            08/08/2026
            Fully Booked
            15/08/2026£1,855.00
            05/09/2026
            Guaranteed
            12/09/2026£1,855.00
            08/05/202715/05/2027£1,925.00
            26/06/202703/07/2027£1,925.00
            07/08/202714/08/2027£1,925.00
            04/09/202711/09/2027£1,925.00
            • Quiet single-track roads for miles on end
            • Bealach Na Ba – the greatest road ascent in the UK
            • Feasting on fresh seafood after a day in the saddle
            • Stunning views out over the Isle of Skye
            • Cycling the peaceful lochside roads of Scotland
            • The swooping coastal road from Ullapool to Kinlochewe
            Photo Highlights Dates
            Guided
            Guided
            Italy

            Alps and Dolomites - Giants of the Giro

            Guided Road Cycling Holiday

            Duration

            9 days

            Prices from

            £2,495 P.P.
            View Reviews
            17
            1
            2
            3
            4
            5
            Grade 4 - 5: Challenging/ Demanding
            More Info BOOK NOW

            Alps and Dolomites - Giants of the Giro

            Guided Road Cycling Holiday

            LAST CHANCE OFFERS!

            Choose half-price bike hire or get 5% off tour departing 22 Aug 2026. Book before 15 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.
            25/07/2026
            Guaranteed
            02/08/2026£2,495.00
            * 22/08/2026
            Guaranteed
            30/08/2026£2,495.00
            17/07/202725/07/2027£2,595.00
            21/08/202729/08/2027£2,595.00
            • 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
            Self-Guided
            Self-Guided
            United Kingdom

            Coast and Castles (4 days cycling)

            Self-Guided Leisure Cycling Holiday

            Duration

            5 days

            Prices from

            £725 P.P.
            View Reviews
            2
            1
            2
            3
            4
            5
            Grade 3-4 : Moderate/Active
            More Info BOOK NOW

            Coast and Castles (4 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.
            30/07/202603/08/2026£725.00
            21/08/202625/08/2026£725.00
            18/09/2026
            Guaranteed
            22/09/2026£725.00

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

            Choose your own dates from:

            2026 £935 per person

            2027 £955 per person

            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:

            • Cycling past the dramatic Tynemouth Priory
            • Miles of pristine dunes and sandy beaches at Druridge Bay
            • Stunning vistas as you approach imposing Bamburgh Castle
            • Your first glimpse of Edinburgh from the Moorfoot hills
            • The rugged beauty of the borders
            • Flexibility to choose your own start date or one of our great value scheduled departure dates
            • A celebratory dram in the shadow of Arthur’s Seat
            Photo Highlights Dates
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            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
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            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
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            Everything about the Skedaddle operation was spot-on, great attention to detail both before and during the trip. I was impressed by all things on the trip, quality of food, route briefings, accommodation, maps. I could go on!
            Paul, Land's End to John O'Groats Classic - 16 Days
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            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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            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
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            On 10+ trips with Skedaddle they have always delivered great trips and service. You get what you pay for and Skedaddle are very good at providing well run cycling holidays.
            Rob, Italy - Sardinia Island Flavours
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