Looking to escape on a spontaneous adventure this August or September? Headwater's last-minute holidays feature a curated collection of self-guided walking trips, ready for immediate booking. Each itinerary is designed to immerse you in stunning landscapes and local culture, with hand-picked accommodations, detailed route notes, and hassle-free luggage transfers. Don’t miss your chance to set off on an unforgettable journey before the season ends.

Need help choosing the perfect trip?

Call our friendly team today — we’re here to answer your questions, share expert advice, and help you find the adventure that’s right for you.

 

United Kingdom : The Channel Islands

Walking in Jersey Premium

$1295

NEW FOR 2025

VIEW TRIP

Self-guided walking

3 nights,
single centre

Level: 1+ & 2

Headwater
Navigation App

VIEW TRIP

Portugal : The Azores

Walking the Green Island of the Azores

$1550


5.0 (3 reviews)

VIEW TRIP

Self-guided walking

7 nights,
single centre

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

Spain : Andalucia

Walking in Sierra de Aracena

$1625


4.8 (15 reviews)

VIEW TRIP

Self-guided walking

7 nights,
hotel-to-hotel

Level: 1
Leisurely

Headwater
Navigation App

VIEW TRIP

Denmark

Cycling from Copenhagen

$1730


5.0 (1 reviews)

VIEW TRIP

Self-guided cycling

4 nights,
single centre

Level: 1
Leisurely

Headwater
Navigation App

VIEW TRIP

Germany : Saxon Switzerland

Walking in the Elbe Sandstone Mountains

$2015

NEW FOR 2025

VIEW TRIP

Self-guided walking

7 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Printed route
directions

VIEW TRIP

France : Brittany

St. Malo to Mont-Saint-Michel Cycling

$2150

 
 

VIEW TRIP

Self-guided cycling

6 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Navigation App

VIEW TRIP

United Kingdom : The Channel Islands

Cycling in Jersey, Guernsey and Sark

$2510


4.0 (1 reviews)

VIEW TRIP

Self-guided cycling

6 nights,
twin centre

Level: 1+
Leisurely plus

Headwater
Navigation App

VIEW TRIP

France : Atlantic Coast

Cycling along the Atlantic Coast

$2960

NEW FOR 2025

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Navigation App

VIEW TRIP

Portugal : Mainland Portugal

Coimbra to Lisbon Cycling

$3185

NEW FOR 2025

VIEW TRIP

Self-guided cycling

11 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

VIEW TRIP

Norway

Cycling Norway's Fjords: Hardangerfjord from Bergen

$4130

NEW FOR 2025

VIEW TRIP

Self-guided cycling

5 nights,
hotel-to-hotel

Level: 2 & 3

Printed route
directions

VIEW TRIP

Norway

Cycling the Norwegian Archipelago South of Bergen

$4640

NEW FOR 2025

VIEW TRIP

Self-guided cycling

6 nights,
hotel-to-hotel

Level: 2 & 3

Printed route
directions

VIEW TRIP

Norway

Walking Norway's Fjords: Hardangerfjord from Bergen

$5090

NEW FOR 2025

VIEW TRIP

Self-guided walking

8 nights,
hotel-to-hotel

Level: 2 & 3

Printed route
directions

VIEW TRIP

Italy : Sicily

Walking the Highlights of Western Sicily

$1895

NEW FOR 2025

VIEW TRIP

Self-guided walking

7 nights,
twin centre

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

Italy : Veneto

Walking in the Venetian Hills

$1835


4.7 (90 reviews)

VIEW TRIP

Self-guided walking

8 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

VIEW TRIP

Italy : The Dolomites

Walking the Dolomites of Alta Badia

$2600


4.8 (26 reviews)

VIEW TRIP

Self-guided walking

7 nights,
single centre

Level: 2+
Moderate plus

Headwater
Navigation App

VIEW TRIP

Switzerland : Valais

Walking in Val D'Anniviers

$2675


4.5 (2 reviews)

VIEW TRIP

Self-guided walking

7 nights,
single centre

Level: 1 to 3

Headwater
Navigation App

VIEW TRIP

Austria : The Danube

Cycling from Vienna to Budapest

$1880


4.6 (65 reviews)

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Navigation App

VIEW TRIP

Switzerland : The Bernese Oberland

Classic Swiss Alps Walk

$1895


4.8 (153 reviews)

VIEW TRIP

Self-guided walking

7 nights,
single centre

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

United Kingdom : Wales

Highlights of the Pembrokeshire Coast

$2135


3.9 (8 reviews)

VIEW TRIP

Self-guided walking

6 nights,
twin centre

Level: 2
Moderate

Printed route
directions

VIEW TRIP

Austria : Salzburg

Austrian Lakes Activities

$2150


4.8 (69 reviews)

VIEW TRIP

Multi-activity holiday

7 nights,
single centre

Level: 1
Leisurely

Headwater
Navigation App

VIEW TRIP

Portugal : Mainland Portugal

Porto Coastal Cycling

$2525


4.4 (59 reviews)

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1
Leisurely

Headwater
Navigation App

VIEW TRIP

Spain : Andalucia

Hidden Valleys of Cordoba Walk

$1055


4.8 (55 reviews)

VIEW TRIP

Self-guided walking

7 nights,
single centre

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

Portugal : Mainland Portugal

Walking the Green Coast of Minho

$1085


4.0 (1 reviews)

VIEW TRIP

Self-guided walking

7 nights,
single centre

Level: 2
Moderate

Printed route
directions

VIEW TRIP

Portugal : Mainland Portugal

Walking the Mountains, Valleys & Coast of Minho

$1340


5.0 (3 reviews)

VIEW TRIP

Self-guided walking

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

VIEW TRIP

Spain : Andalucia

Walking the White Villages of the Alpujarras

$1445


4.6 (7 reviews)

VIEW TRIP

Self-guided walking

7 nights,
hotel-to-hotel

Level: 2 & 2+

Headwater
Navigation App

VIEW TRIP

Romania : Transylvania

Transylvanian Castles Walk

$1520


4.9 (20 reviews)

VIEW TRIP

Self-guided walking

7 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
Navigation App

VIEW TRIP

Switzerland : The Bernese Oberland

Walking in Kandersteg - Short Break

$1580


4.9 (12 reviews)

VIEW TRIP

Self-guided walking

5 nights,
single centre

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

Slovakia

Walking the Tatra Mountains in Slovakia

$1640

NEW FOR 2025

VIEW TRIP

Self-guided walking

7 nights,
twin centre

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

Czechia

Walking through Bohemia

$1775


4.9 (7 reviews)

VIEW TRIP

Self-guided walking

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

VIEW TRIP

United Kingdom : Devon

Walking South Devon's Coastal Path

$1775


5.0 (1 reviews)

VIEW TRIP

Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

France : The Loire

Multi Activity in the Loire

$1790


5.0 (2 reviews)

VIEW TRIP

Multi-activity holiday

5 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Navigation App

VIEW TRIP

France : The Loire

Cycling The UNESCO Loire Valley

$1805


5.0 (4 reviews)

VIEW TRIP

Self-guided cycling

5 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Navigation App

VIEW TRIP

Austria : The Tyrol

Alpine Walks in the Stubai Valley

$1805


4.7 (12 reviews)

VIEW TRIP

Self-guided walking

7 nights,
single centre

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

United Kingdom : Wales

Highlights of the Gower Peninsula Walk

$1865


5.0 (2 reviews)

VIEW TRIP

Self-guided walking

5 nights,
twin centre

Level: 1+
Leisurely plus

Headwater
Navigation App

VIEW TRIP

Austria : Salzburg

Walking the Tyrolean Mountains

$1895


4.7 (3 reviews)

VIEW TRIP

Self-guided walking

6 nights,
single centre

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

Italy : Campania

Coastal Cilento Walk

$1895


4.9 (8 reviews)

VIEW TRIP

Self-guided walking

8 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
Navigation App

VIEW TRIP

Switzerland : Davos

Walk the Crossroads of Five Passes

$1925


4.9 (8 reviews)

VIEW TRIP

Self-guided walking

7 nights,
single centre

Level: 1 to 3

Headwater
Navigation App

VIEW TRIP

Austria : Salzburg

Cycling the Lakes and Rivers of the Salzkammergut

$1940


5.0 (1 reviews)

VIEW TRIP

Self-guided cycling

6 nights,
single centre

Level: 2
Moderate

Navigation App

VIEW TRIP

Bosnia

Walking the Olympic Mountains of Bosnia

$1985

NEW FOR 2025

VIEW TRIP

Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

France : Normandy

D-Day Beaches Of Normandy Cycling

$2000


4.6 (7 reviews)

VIEW TRIP

Self-guided cycling

5 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Printed route
directions

VIEW TRIP

United Kingdom : The Channel Islands

Walking in Jersey, Guernsey and Sark

$2030


4.4 (16 reviews)

VIEW TRIP

Self-guided walking

6 nights,
twin centre

Level: 1+ & 2

Headwater
Navigation App

VIEW TRIP

France : Normandy

Normandy Walk from Deauville to Bayeux

$2030


4.7 (6 reviews)

VIEW TRIP

Self-guided walking

7 nights,
hotel-to-hotel

Level: 1
Leisurely

Printed route
directions

VIEW TRIP

Germany : Bavaria

Lakes and Mountains of Bavaria Cycling

$2120


4.4 (5 reviews)

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Navigation App

VIEW TRIP

United Kingdom : Norfolk

Highlights of Norfolk Cycling

$2135


4.4 (11 reviews)

VIEW TRIP

Self-guided cycling

5 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

VIEW TRIP

France : Canal du Midi

Canal du midi Cycling : from Toulouse to Sete

$2180


4.8 (5 reviews)

VIEW TRIP

Self-guided cycling

6 nights,
hotel-to-hotel

Level: 2
Moderate

Navigation App

VIEW TRIP

France : The Loire

Canoeing on the Loire

$2195


4.0 (1 reviews)

VIEW TRIP

5 nights,
hotel-to-hotel

Navigation App



VIEW TRIP

France : Burgundy

Cycling the Vineyards From Beaune to Macon

$2195


4.8 (6 reviews)

VIEW TRIP

Self-guided cycling

6 nights,
hotel-to-hotel

Level: 1
Leisurely

Printed route
directions

VIEW TRIP

Belgium

Cycling from Brussels to Bruges

$2225


4.0 (2 reviews)

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Navigation App

VIEW TRIP

Germany : The Moselle

Meandering the Moselle Cycle Path

$2225

NEW FOR 2025

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1
Leisurely

Printed route
directions

VIEW TRIP

United Kingdom : Wales

Walking Offa's Dyke Path (South)

$2225

 
 

VIEW TRIP

Self-guided walking

8 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
Navigation App

VIEW TRIP

France : The Loire

Cycling The Chateaux Of The Loire

$2255


4.5 (12 reviews)

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Navigation App

VIEW TRIP

France : The French Riviera

The French Riviera Golden Islands

$2270

NEW FOR 2025

VIEW TRIP

Self-guided walking

7 nights,
twin centre

Level: 1+
Leisurely plus

Printed route
directions

VIEW TRIP

France : Normandy

Paris to the Sea Along the Seine River

$2750

NEW FOR 2025

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Printed route
directions

VIEW TRIP

France : The Loire

Cycling The Chateaux Of The Loire - Upgraded

$2780


4.8 (8 reviews)

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Navigation App

VIEW TRIP

Portugal : Mainland Portugal

Porto to Coimbra Cycling

$2945


4.8 (56 reviews)

VIEW TRIP

Self-guided cycling

9 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

VIEW TRIP

Denmark

Nordic Cities by Rail

$2945

NEW FOR 2025

VIEW TRIP

Self-guided cultural tour

9 nights,
hotel-to-hotel



VIEW TRIP
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
  • Faroe Islands
  • Germany
  • Holland
  • Ireland
  • Malta
  • Montenegro
  • Norway
  • Romania
  • Slovakia
  • Slovenia
  • Sweden
  • Switzerland
  • USA

Departure month
All

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

Activity 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
  • Dog friendly
  • Coastal routes
  • Island exploring
  • Lakes and rivers
  • High peaks
  • Unique accommodation
  • Parador hotels
  • 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.

Back to top