Self-Guided Cycling Holidays

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!

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Self-Guided

Spain

Bilbao to Santiago

Self-Guided Road Cycling Holiday

Duration

10 days

Prices from

£2,055 P.P.

Grade 3 : Moderate

More Info BOOK NOW

Bilbao to Santiago

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.

2026 05 Apr – 31 Oct

Season 1 – £2055 22 – 31 May / 29 Sep – 31 Oct

Season 2 – £2265 01 Jun – 31 Jul / 01 – 28 Sep

Season 3 – £2495 05 – 12 Apr / 01 – 31 Aug

2027 29 Mar – 31 Oct

Season 1 – £2055 29 Mar – 29 Apr / 03 May – 03 Jun / 26 Sep – 31 Oct

Season 2 – £2265 04 Jun – 15 Jul / 05 – 25 Sep

Season 3 – £2495 16 Jul – 04 Sep

Riding along the stunning and dramatic Cantabrian coastline
A stunning start in the Basque city of Bilbao
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

Photo Highlights Dates

Self-Guided

Italy

Strade Bianche Explorer

Self-Guided Gravel Riding Holiday

Duration

8 days

Prices from

£1,895 P.P.

View Reviews

Grade 3-4 : Moderate/Challenging

More Info BOOK NOW

Strade Bianche Explorer

Self-Guided Gravel Riding 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.

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

Season 1 – £1895 29 Mar – 14 Jun and 09 Sep – 26 Oct

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

2027 30 Mar – 26 Oct (excluding dates throughout July and August)

Season 1 – £1995 30 Mar – 14 Jun and 09 Sep – 26 Oct

Season 2 – £2195 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.

Riding some of the classic Strade Bianche route of Tuscany as well as lesser-known gravel routes
Cycling through the historic wine regions of Tuscany, stopping off for a bit of wine tasting
Exploring the region on a mix of terrains
Riding the stunning UNESCO heritage region of Val d’Orcia
Relaxing in small villages for a coffee with the locals
Easing along the rolling hills of the ‘Colli Senesi’
Chilling out with a post-ride Chianti or Brunello

Photo Highlights Dates

Self-Guided

Ireland

Kerry to Cork

Self-Guided Leisure Cycling Holiday

Duration

9 days

Prices from

£1,895 P.P.

Grade 4: Active

More Info BOOK NOW

Kerry to Cork

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.

2026 Daily departures available from 01 Apr to 10 Oct.

£1895 per person.

World famous fish and chips in the beautiful seaside town of Kinsale
Captivating scenes of patchwork green fields laid before you in the Glorious Borlin Valley
Enjoying rural coastal towns and villages
Spectacular views over the Gap of Dunloe and the Black Valley
Admiring the stone circles and standing stones that bring Ireland’s long history to life
Enjoying the ever-charming city of Cork

Photo Highlights Dates

Not sure which trip's right for you? Just ask!

Get in touch and we'll help you find your perfect trip.

Self-Guided Cycling Holidays

Bilbao to Santiago

Self-Guided Road Cycling Holiday

Duration

Prices from

Bilbao to Santiago

Self-Guided Road Cycling Holiday

Strade Bianche Explorer

Self-Guided Gravel Riding Holiday

Duration

Prices from

Strade Bianche Explorer

Self-Guided Gravel Riding Holiday

Kerry to Cork

Self-Guided Leisure Cycling Holiday

Duration

Prices from

Kerry to Cork

Self-Guided Leisure Cycling Holiday

E-BIKE HIRE AVAILABLE

Not sure which trip's right for you? Just ask!

News, Reviews & Stories

The Lowdown on Gallovidian Gravel

Customer Story - An Iconic Journey Across Spain and Portugal

Summer cycling advice: 10 top tips

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Self-Guided Cycling Holidays

2026

2027

2028

2026

2027

2028

Bilbao to Santiago

Self-Guided Road Cycling Holiday

Duration

Prices from

Bilbao to Santiago

Self-Guided Road Cycling Holiday

Strade Bianche Explorer

Self-Guided Gravel Riding Holiday

Duration

Prices from

Strade Bianche Explorer

Self-Guided Gravel Riding Holiday

Kerry to Cork

Self-Guided Leisure Cycling Holiday

Duration

Prices from

Kerry to Cork

Self-Guided Leisure Cycling Holiday

E-BIKE HIRE AVAILABLE

Not sure which trip's right for you? Just ask!

News, Reviews & Stories

The Lowdown on Gallovidian Gravel

Customer Story - An Iconic Journey Across Spain and Portugal

Summer cycling advice: 10 top tips