We are the self-guided specialists, with an incredible range of relaxed walking and cycling holidays to tempt you to change the way you think about your next escape. Uncover the perfect balance between relaxation and discovery with an unforgettable walking or cycling holiday.

Since 1985 we have been creating relaxed walking and cycling holidays across the UK, Europe, and beyond. Our tailor-made tours combine winning routes, idyllic destinations and hand-picked accommodation (with delicious local cuisine) for all levels of walker or cyclist.

Our expertly curated itineraries are designed to activate the senses, immersing you deeper into your region's local culture, where you can visit places of historical interest, sample food that epitomizes the local cuisine and enjoy enchanting stays in characterful accommodations. Rest assured, we'll help you find the hidden treasures, the lesser-known path, and the best regional cuisine. You'll soon find there's an incredible world to wander, pedal and absorb in 2023.

£100 off Headwater trips  
We’re offering you the chance to save £100 off any Headwater holiday. Simply use code CN100 when booking with one of our expert team. See full terms and conditions at the bottom of this page.

Win a Headwater Holiday  
Can't wait to get out and experience a self-guided holiday this summer? Enter our competition to be in with the chance of winning a Headwater holiday for two, from a choice of Secrets of Sicily Walking Holiday or Contrasts of Catalunya Cycling Holiday . To enter, simply enter your details below – the winner will be selected on the 5th April – good luck! See full terms and conditions at the bottom of this page.

Terms and conditions apply.


Why choose Headwater?

 

Slovenia

Julian Alps to the Adriatic Cycling

£1889


4.8 (118 reviews)

VIEW TRIP

Self-guided cycling

10 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

Austria

Cycling from Vienna to Budapest

£1019


4.6 (49 reviews)

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Navigation App

France : The Dordogne

Dordogne Valleys & Villages Cycling

£1069


4.7 (42 reviews)

VIEW TRIP

Self-guided cycling

8 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

Italy : Puglia

Contrasts of Puglia Cycling

£1279


4.6 (123 reviews)

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

Spain : Andalucia

Cycling in Andalucia: Seville to Cadiz

£1349


4.3 (12 reviews)

VIEW TRIP

Self-guided cycling

6 nights,
hotel-to-hotel

Level: 3
Stretching

Headwater
Navigation App

United Kingdom : Norfolk

Contrasts of Norfolk Cycling

£1379


5.0 (1 reviews)

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

Austria : Carinthia

Lake Constance Cycling

£1389


4.7 (88 reviews)

VIEW TRIP

Self-guided cycling

10 nights,
hotel-to-hotel

Level: 1
Leisurely

Headwater
Navigation App

Tap here to filter results

Filter and sort

Holiday type
All

  • Self-guided walking
  • Self-guided cycling
  • Ski holidays
  • Canoeing
  • Multi activity
  • Pilgrimage
  • Private guided walking
  • Cultural tour
  • Guided group walking
  • Guided group cycling

Destination
All

  • Italy
  • Spain
  • France
  • Portugal
  • UK
  • Andorra
  • Austria
  • Belgium
  • Bermuda
  • Bosnia
  • Canada
  • Cape Verde
  • China
  • Croatia
  • Czechia
  • Denmark
  • Finland
  • Germany
  • Gozo
  • Holland
  • Ireland
  • Malta
  • Montenegro
  • Norway
  • Romania
  • Slovenia
  • Sweden
  • Switzerland
  • USA

Departure month
All

  • Jan
  • Feb
  • Mar
  • Apr
  • May
  • Jun
  • Jul
  • Aug
  • Sep
  • Oct
  • Nov
  • Dec

Activty level
All


  • Leisurely

  • Moderate

  • Demanding

  • Challenging

Accommodation type
All


  • Single centre

  • Twin centre  

  • Hotel-to-hotel

Best for
All

  • Singles
  • Couples
  • Families
  • Food lovers
  • Wine lovers
  • Nature lovers
  • Bird watchers
  • Historic sites
  • Vegetarians
  • Swimming opportunities
  • Electric bikes
  • Tandem bikes
  • GPS navigation
  • Coastal routes
  • Island exploring
  • Lakes and rivers
  • High peaks
  • Unique accommodation
  • New holidays
  • Bestsellers

Sorted by


  • Price

  • Duration

  • Level

Update filters

 

Where appropriate, we grade our holidays based on distance, terrain, elevation gain, remoteness, etc and categorise them into 4 relative groups. This is ultimately subjective and may vary slightly day to day; for more advice, please see the specific trip page or call one of our friendly team.


Terms & Conditions



  • Competition Terms and conditions
  • To enter the competition, you must provide your name and email address. If you have any questions about how to enter or in connection with the competition, please email us at mktg@exodus.co.uk
  • The prize is for 2 on either our Secrets of Sicily Walking Holiday or Contrasts of Catalunya Cycling Holiday. One winner will be chosen from competition run across the Future Network.
  • The prize includes return economy flights – airline chosen by Headwater Travels, accommodation, meals, transfers as outlined on the trip pages: Secrets of Sicily Walking Holiday or Contrasts of Catalunya Cycling
  • The prize does not include transfers to/from airport (in the UK), pre/post nights’ accommodation, travel insurance or any optional activities not stated in the itinerary on the Headwater website.
  • The competition is open to UK entrants only.
  • Entrants must be 18 years or over.
  • Offer valid on any departure up to 31st December 2023, subject to availability.
  • The holiday is offered in accordance with Headwater’s standard booking conditions and is subject to availability.
  • No employees of Headwater, The Travelopia Group, their subsidiaries, group companies or other company associated with this promotion will be eligible to enter.
  • The opening date is 00.01 on 6th February 2023. The closing date is midnight on the 31st March 2023.
  • The winner will be selected at random. The decision of Headwater will be final. No correspondence will be entered into.
  • If the winner does not accept the prize or if contact cannot be made within 28 days of the draw, the prize will be forfeited and offered to a substitute winner. It is the entrant's responsibility to notify Exodus of any change in contact information.
  • If you are the winner, you may be required to participate in any publicity or promotion organised by the Promoter; this may include printing your name on the Headwater website at www.headwater.com
  • The prize is not transferable; it is only for the use of the winner (i.e. the lead passenger) and there is no cash alternative.
  • The promoter is Exodus Travels Limited t/a Headwater, a member of the Travelopia Group of Companies. Registered UK Office: Origin One, 108 High Street, Crawley, West Sussex, RH10 1BD.
  • Details of the winner will be available by sending a SAE to the Promoter after 27th March 2023 at the following address: Exodus Travels, DST House, St Mark's Hill, Surbiton KT6 4BH.
  • Entry into this competition implies acceptance of these rules and conditions. Standard booking terms and conditions apply.

    £100 offer Terms and conditions
  • Please quote offer code CN100 at the time of booking.
  • Valid on bookings made between 09/01/2022 and 31/03/2023 only.
  • Valid on selected departures between 12/01/2023 and 31/12/2023 only.
  • Valid on new bookings only, cannot be applied to existing bookings, cannot be used to rebook the same trip, or to rebook any trip cancelled after 1 December 2022.
  • A deposit of 30% will be required at the time of booking to secure your arrangements.
  • The discount will be applied to your final balance, not your deposit amount.
  • This offer is not combinable with any other offers, including Loyalty Discounts.
  • The discount only applies to the tour price, not to any additional items such as international flights, single supplements or optional extra accommodation.
  • All other Headwater standard booking terms and conditions apply.
  • Flight supplements may still apply.
  • This offer is subject to availability and Headwater Holidays reserves the right to change this offer at any time.
  • This offer is not transferrable, there is no cash alternative, and no correspondence will be entered into.
  • This offer is not available to Headwater staff or their immediate families.

Back to top