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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 4 of 9

            Select Order Order By
            Guided
            Guided
            Italy

            Lakes of Lombardia

            Guided Road Cycling Holiday

            Duration

            8 days

            Prices from

            £2,395 P.P.
            View Reviews
            23
            1
            2
            3
            4
            5
            Grade 3 : Moderate
            More Info BOOK NOW

            Lakes of Lombardia

            Guided Road Cycling Holiday

            Start DateEnd DatePrice p.p.
            11/07/2026
            Guaranteed
            18/07/2026£2,395.00
            01/08/2026
            Contact Us
            08/08/2026£2,395.00
            10/07/202717/07/2027£2,495.00
            31/07/202707/08/2027£2,495.00
            • 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

            Sardinia - Island Flavours

            Guided Leisure Cycling Holiday

            Duration

            8 days

            Prices from

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

            Sardinia - Island Flavours

            Guided Leisure Cycling Holiday

            LAST CHANCE OFFERS!

            Choose half-price bike hire or get 5% off tour departing 10 Oct 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.
            12/09/2026
            Last Spaces
            19/09/2026£1,995.00
            * 10/10/2026
            Guaranteed
            17/10/2026£1,995.00
            17/04/202724/04/2027£2,095.00
            01/05/202708/05/2027£2,095.00
            11/09/202718/09/2027£2,095.00
            09/10/202716/10/2027£2,095.00
            • Checking out the UNESCO heritage site of Barumini Nuraghe
            • Enjoying the long descent to Fluminimaggiore and Masua
            • Sampling local specialties at Carloforte, on St Pietro island
            • Riding along the Nebida coastline and marvelling at the view of Pan di Zucchero
            • Experiencing the friendliness and hospitality of the Sardinian people
            • Discovering the white beaches along the south-west coastal road
            Photo Highlights Dates
            Guided
            Guided
            Italy

            Tuscany - Giro della Toscana

            Guided Road Cycling Holiday

            Duration

            8 days

            Prices from

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

            Tuscany - Giro della Toscana

            Guided Road Cycling Holiday

            Start DateEnd DatePrice p.p.
            29/08/202605/09/2026£2,095.00
            03/10/2026
            Fully Booked
            10/10/2026£2,095.00
            01/05/202708/05/2027£2,195.00
            29/05/202705/06/2027£2,195.00
            02/10/202709/10/2027£2,195.00
            • 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
            Self-Guided
            Self-Guided
            United Kingdom

            Hadrian's Cycleway (4 days cycling)

            Self-Guided Leisure Cycling Holiday

            Duration

            5 days

            Prices from

            £595 P.P.
            View Reviews
            2
            1
            2
            3
            4
            5
            Grade 2-3: Gentle/Moderate
            More Info BOOK NOW

            Hadrian's Cycleway (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.
            24/07/2026
            Guaranteed
            28/07/2026£595.00
            07/08/2026
            Fully Booked
            11/08/2026£595.00

            Daily departures available from April to mid October.

            Choose your own dates from:

            2026 £725 per person

            2027 £740 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.

            • 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
            Self-Guided
            Self-Guided
            United Kingdom

            Hadrian's Cycleway (4 days cycling)

            Self-Guided Family Cycling Holiday

            Duration

            5 days

            Prices from

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

            Hadrian's Cycleway (4 days cycling)

            Self-Guided Family Cycling Holiday

            Child Discounts

            Daily departures available from April to mid October.

            Choose your own dates from:

            2026 £725 per person

            2027 £740 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.

            Kid’s Discounts

            For children below the age of 18 who are travelling with 2 full-paying passengers, we are able to offer a 20% discount off the basic holiday cost.

            If you‘re happy sharing a family room, once we’ve received your booking we will check what rooms are available and we may be able to offer (up to) an additional 20% discount for the children (subject to availability).

            • Cycling next to Hadrian’s Wall near Birdoswald
            • Seeing a live archaeological dig at Vindolanda
            • Beating your parents up one of the cheeky Skedaddle climbs
            • Corbridge and sinking a well-deserved pint of local ales not all about the kids you know!!
            • Seeing who’ll be the first to spot the Blinking Eye bridge in Newcastle
            • Ice cream in Tynemouth and the sense of achievement having ridden from coast to coast as a family
            Photo Highlights Dates
            Guided
            Guided
            France

            Haute Dordogne

            Guided Road Cycling Holiday

            Duration

            8 days

            Prices from

            £2,495 P.P.
            View Reviews
            6
            1
            2
            3
            4
            5
            Grade 2 - 3: Gentle to Moderate
            More Info BOOK NOW

            Haute Dordogne

            Guided Road Cycling Holiday

            LAST CHANCE OFFERS!

            LAST CHANCE OFFERS! Choose half-price bike hire or get 5% off tours departing 5 Sep 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.
            * 05/09/2026
            Guaranteed
            12/09/2026£2,495.00
            05/06/202712/06/2027£2,595.00
            28/08/202704/09/2027£2,595.00
            • Sampling a glass of red in Cahors – home of Malbec
            • Winding our way along the dramatic Vallée du Célé
            • Cycling along to the sound of cowbells near Velzic
            • Conquering the Pas de Peyrol and drinking in the views
            • Rocamadour and the descent from its lofty heights
            • Marvelling at the Massif Centrale as we cycle through its distinctive landscapes
            Photo Highlights Dates
            Self-Guided
            Self-Guided
            UK

            Hadrian's Cycleway (6 days cycling)

            Self-Guided Leisure Cycling Holiday

            Duration

            7 days

            Prices from

            £895 P.P.
            View Reviews
            6
            1
            2
            3
            4
            5
            Grade 1-2 : Easy/Gentle
            More Info BOOK NOW

            Hadrian's Cycleway (6 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.

            Daily departures available from April to mid October.

            Choose your own dates from:

            2026 £895 per person

            2027 £915 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 well preserved forts of Birdoswald and Vindolanda
            • The rugged beauty of the North Pennines
            • The view down the Tyne as you arrive in to Newcastle
            • The picturesque market town of Corbridge
            • The sense of achievement having ridden from coast to coast
            • Following in the footsteps of the Roman Empire
            Photo Highlights Dates
            Guided
            Guided
            France

            Alps - Mont Ventoux to Alpe d'Huez

            Guided Road Cycling Holiday

            Duration

            8 days

            Prices from

            £2,595 P.P.
            View Reviews
            9
            1
            2
            3
            4
            5
            Grade 4 : Challenging
            More Info BOOK NOW

            Alps - Mont Ventoux to Alpe d'Huez

            Guided Road Cycling Holiday

            Start DateEnd DatePrice p.p.
            14/06/2026
            Guaranteed
            21/06/2026£2,595.00
            16/08/2026
            Contact Us
            23/08/2026£2,595.00
            26/06/202703/07/2027£2,695.00
            24/07/202731/07/2027£2,695.00
            • Legendary Tour de France challenges every day
            • ‘Warming up’ on Mont Ventoux, the ‘Giant of Provence’
            • Blue skies, fresh air and snow-capped peaks
            • ‘Top of the world’ sensations on the summit of the Izoard
            • Ticking off lots of Tour de France classics
            • Riding through Provençal lavender flelds, synonymous with the region
            • The final challenge of the legendary Alpe d‘Huez
            Photo Highlights Dates
            Guided
            Guided
            Spain

            Bilbao to Barcelona

            Guided Road Cycling Holiday

            Duration

            10 days

            Prices from

            £2,995 P.P.
            View Reviews
            2
            1
            2
            3
            4
            5
            Grade 3 - 4: Moderate/ Challenging
            More Info BOOK NOW

            Bilbao to Barcelona

            Guided Road Cycling Holiday

            LAST CHANCE OFFERS!

            Choose half-price bike hire or get 5% off tour departing 3 Sep 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.
            * 03/09/2026
            Guaranteed
            12/09/2026£2,995.00
            24/09/2026
            Last Spaces
            03/10/2026£2,995.00
            12/05/202721/05/2027£3,085.00
            03/09/202712/09/2027£3,085.00
            25/09/202704/10/2027£3,085.00
            • 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
            Guided
            Guided
            Spain

            Basque Country to Andalucia Classic - North to South

            Guided Road Cycling Holiday

            Duration

            16 days

            Prices from

            £3,995 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

            Start DateEnd DatePrice p.p.
            27/09/202612/10/2026£3,995.00
            11/04/202726/04/2027£4,095.00
            25/09/202710/10/2027£4,095.00
            • 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
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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
            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
            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
            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
            Quote
            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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            News, Reviews & Stories

            Customer Story - An Iconic Journey Across Spain and Portugal

            We caught up with Russ, our biggest iconic journeys fan on our new Trans Iberia route from Barcelona to Porto across Spain & Portugal.

            Summer cycling advice: 10 top tips

            Planning a summer cycling holiday? Discover practical hot weather tips on hydration, kit and pacing, to stay safe during summer bike tours.

            Mountain Biking Across Sardinia

            The story behind our most popular mountain bike holiday in Italy which has been running for more than 20 years!

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