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            Self-Guided Cycling Holidays

            We found 71 Holidays in your search for:

            Destinations (81)
            Types of Cycling / Grades (7)
            Departure Month

            2025

            2026

            2027

            Level of Support

            We found 71 Holidays in your search for:

            Select Order Order By
            Destinations (81)
            Types of Cycling / Grades (7)
            Departure Month

            2025

            2026

            2027

            Level of Support

            There’s something special about being able to pedal off on your very own cycling adventure. On a self-guided tour with Skedaddle, we’ll take care of the essential details - the route planning, navigation tools, accommodation, luggage transfers, hire bikes and emergency back-up, leaving you and your friends to enjoy the ride.

            We have a huge selection of self-guided holidays in Europe and the UK across all types of cycling – leisure, road cycling, mountain biking and gravel riding so you can find your perfect cycling escape. Choose the dates that work for you and let us take care of the rest!

            • All Cycling Holidays
            • ALL SELF-GUIDED HOLIDAYS

            Page 5 of 8

            Select Order Order By
            Self-Guided
            Self-Guided
            Italy

            Classic Tuscany

            Self-Guided Leisure Cycling Holiday

            Duration

            7 days

            Prices from

            £1,335 P.P.
            View Reviews
            7
            1
            2
            3
            4
            5
            Grade 3 : Moderate
            More Info BOOK NOW

            Classic Tuscany

            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. 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.

            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 – £1335 24 Mar – 16 Jun and 03 Sep – 29 Oct

            Season 2 – £1575 17 Jun – 30 Jun and 01 – 02 Sep

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

            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.

            • Staying at Tuscan farms overlooking stunning countryside
            • Visiting the famous towns of Monteriggioni, Radda in Chianti and Siena
            • Riding through wonderful landscapes, wide open fields, cypress-lined hills and vineyards
            • Trying delicious, regional dishes
            • Sampling the best wines of Chianti, Montepulciano and Montalcino
            • Absorbing the atmosphere of San Gimignano – a UNESCO World Heritage Site
            Photo Highlights Dates
            Self-Guided
            Self-Guided
            Italy

            Sardinia - Coastal Explorer

            Self-Guided Road Cycling Holiday

            Duration

            8 days

            Prices from

            £1,475 P.P.
            View Reviews
            8
            1
            2
            3
            4
            5
            Grade 2 - 3: Gentle to Moderate
            More Info BOOK NOW

            Sardinia - Coastal Explorer

            Self-Guided Road Cycling Holiday

            SAVE ON 2026 ESCAPES

            Save £75 on this holiday when you book before 31 October 2025. Enter promo code BN26 when you book and your discount will be applied after your booking is confirmed. Ts and Cs apply.

            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 – £1475 24 Mar – 08 Jun and 09 Sep – 29 Oct

            Season 2 – £1685 01 Sept – 08 Sept

            2026 29 Mar – 26 Oct (excluding dates from 08 Jun – 31 Aug)

            Season 1 – £1550 26 Mar – 07 Jun and 09 Sep – 29 Oct

            Season 2 – £1775 01 Sept – 08 Sept

            SAVE ON 2026 ESCAPES

            Save £75 on this holiday when you book before 31 October 2025. Enter promo code BN26 when you book and your discount will be applied after your booking is confirmed. Ts and Cs apply..

            • Riding the stunning coastal road from Alghero to Bosa
            • Exploring the sandstone coast of Santa Caterina di Pittinuri
            • Visiting the Sinis Peninsula and the ancient Roman ruins of Tharros
            • The view of Pan di Zucchero on the Nebida coastal ride
            • Sweeping down the long descent to Fluminimaggiore and Masua
            • Exploring the white beaches running alongside the south west coastal road
            Photo Highlights Dates
            Self-Guided
            Self-Guided
            UK

            Hadrian's Cycleway (6 days cycling)

            Self-Guided Leisure Cycling Holiday

            Duration

            7 days

            Prices from

            £935 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 £935 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
            Self-Guided
            Self-Guided
            United Kingdom

            Hadrian's Cycleway (6 days cycling)

            Self-Guided Family Cycling Holiday

            Duration

            7 days

            Prices from

            £935 P.P.
            1
            2
            3
            4
            5
            Grade 1 - 2 : Easy/Gentle
            More Info BOOK NOW

            Hadrian's Cycleway (6 days cycling)

            Self-Guided Family Cycling Holiday

            Daily departures available from April to mid October.

            Choose your own dates from:

            2026 £935 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 25% 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 25% discount for the children (subject to availability).

            • Cycling next to Hadrian’s Wall near Birdoswald
            • Beating your parents up one of the cheeky Skedaddle climbs
            • Seeing a live archaeological dig at Vindolanda
            • Corbridge and sinking a well-deserved pint of local ale – it’s 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
            Self-Guided
            Self-Guided
            Portugal

            Azure Ocean Ride

            Self-Guided Leisure Cycling Holiday

            Duration

            8 days

            Prices from

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

            Azure Ocean Ride

            Self-Guided Leisure Cycling Holiday

            SAVE ON 2026 ESCAPES

            Save £100 on this holiday when you book before 31 October 2025. Enter promo code BN26 when you book and your discount will be applied after your booking is confirmed. Ts and Cs apply.

            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 05 Jan – 13 Dec

            Season 1 – £1795 05 Jan – 29 Jun and 15 Sep – 13 Dec

            Season 2 – £2135 30 Jun – 14 Sep

            2026 05 Jan – 13 Dec (excl. Easter week between 29 Mar and 05 Apr and St John’s Day 23/24 Jun)

            Season 1 – £1825 05 Jan – 30 Jun and 16 Sep – 13 Dec

            Season 2 – £2195 01 Jul – 15 Sep

            Worth noting We run this tour from Jan through to Dec. The summer months however (generally from 01 Jul – 15 Sep) can be really busy. More people, more cyclists, busier restaurants, busier hotels etc, so we’d recommend travelling in the Spring or Autumn if you‘re looking for a quieter getaway with less cyclists to share the route with.

            Please note We are generally not able to confirm any bookings for this tour made within 4 weeks of departure. Please contact our office if you are looking to book and begin your holiday within this period and we will do our best to accommodate your request.

            SAVE ON 2026 ESCAPES

            Save £100 on this holiday when you book before 31 October 2025. Enter promo code BN26 when you book and your discount will be applied after your booking is confirmed. Ts and Cs apply.

            • 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
            • Visiting the lovely Vimeiro
            Photo Highlights Dates
            Self-Guided
            Self-Guided
            Italy

            Tuscany - Giro della Toscana

            Self-Guided Road Cycling Holiday

            Duration

            8 days

            Prices from

            £1,625 P.P.
            View Reviews
            4
            1
            2
            3
            4
            5
            Grade 3 : Moderate
            More Info BOOK NOW

            Tuscany - Giro della Toscana

            Self-Guided Road Cycling Holiday

            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 in July and August)

            Season 1 – £1625 24 Mar – 16 Jun and 03 Sep – 29 Oct

            Season 2 – £1925 17 Jun – 30 Jun and 01 – 02 Sep

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

            Season 1 – £1695 29 Mar – 14 Jun and 09 Sep – 26 Oct

            Season 2 – £2025 15 Jun – 30 Jun and 01 – 08 Sep

            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.

            • 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

            £615 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.
            05/06/202609/06/2026£615.00
            24/07/2026
            Guaranteed
            28/07/2026£615.00
            14/08/202618/08/2026£615.00

            Daily departures available from April to mid October.

            Choose your own dates from:

            2026 £725 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

            Daily departures available from April to mid October.

            Choose your own dates from:

            2026 £725 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 25% 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 25% 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
            Self-Guided
            Self-Guided
            United Kingdom

            Coast and Castles (4 days cycling)

            Self-Guided Leisure Cycling Holiday

            Duration

            5 days

            Prices from

            £755 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.
            22/05/202626/05/2026£755.00
            12/06/202616/06/2026£755.00
            10/07/202614/07/2026£755.00
            21/08/202625/08/2026£755.00

            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 £985 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
            Self-Guided
            Self-Guided
            United Kingdom

            Hadrian's Cycleway (3 days cycling)

            Self-Guided Leisure Cycling Holiday

            Duration

            4 days

            Prices from

            £525 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.
            05/06/202608/06/2026£525.00
            24/07/202627/07/2026£525.00
            14/08/202617/08/2026£525.00

            Daily departures available from April to mid October.

            Choose your own dates from:

            2026 £615 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
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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
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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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