BOOK NOW & CLAIM YOUR FREE CASE OF VIRGIN WINES.

 

AUTUMN ADVENTURES

As the summer crowds fade and landscapes turn golden, autumn is the perfect time to explore. Whether you're chasing autumnal colours, cosy escapes, or late-season sun, we've handpicked the best destinations to visit in September and October.

Below, we've put together a helpful list of our top picks for Autumn.

 

United Kingdom : Devon

The English Riviera & Dart Valley Walk

£549


5.0 (1 reviews)

VIEW TRIP

Self-guided walking

4 nights,
twin centre

Level: 2
Moderate

Printed route
directions

FREE CASE OF WINE WITH BOOKING

VIEW TRIP

Slovenia

Lake Bled and Lake Bohinj Walk

£779


4.6 (31 reviews)

VIEW TRIP

Self-guided walking

7 nights,
single centre

Level: 1+
Leisurely plus

Printed route
directions

FREE CASE OF WINE WITH BOOKING

VIEW TRIP

Italy : The Bay of Naples

The Islands of Amalfi Walk

£1109


4.6 (14 reviews)

VIEW TRIP

Self-guided walking

7 nights,
twin centre

Level: 2
Moderate

Headwater
Navigation App

FREE CASE OF WINE WITH BOOKING

VIEW TRIP

United Kingdom : Scotland

Walking the Rob Roy Way

£1229

 
 

VIEW TRIP

Self-guided walking

8 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Navigation App

FREE CASE OF WINE WITH BOOKING

VIEW TRIP

United Kingdom : Scotland

Walking the West Highland Way

£1249


4.3 (4 reviews)

VIEW TRIP

Self-guided walking

8 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Navigation App

FREE CASE OF WINE WITH BOOKING

VIEW TRIP

France

St. Malo to Mont-Saint-Michel Cycling

£1309

 
 

VIEW TRIP

Self-guided cycling

6 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Navigation App

FREE CASE OF WINE WITH BOOKING

VIEW TRIP

Portugal : The Algarve

Walking Rota Vicentina North Fishermen's Trail

£1369


4.5 (2 reviews)

VIEW TRIP

Self-guided walking

8 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

FREE CASE OF WINE WITH BOOKING

VIEW TRIP

Portugal : Mainland Portugal

Cycling in the Douro Valley

£1519

 
 

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 3
Stretching

Headwater
Navigation App

FREE CASE OF WINE WITH BOOKING

VIEW TRIP

Italy : Italian Lakes

Walking at Lakes Orta and Maggiore

£1549

NEW FOR 2025

VIEW TRIP

Self-guided walking

8 nights,
hotel-to-hotel

Level: 1+ & 2

Headwater
Navigation App

FREE CASE OF WINE WITH BOOKING

VIEW TRIP

Switzerland : The Bernese Oberland

Cycling the Swiss Lakes - Vevey to Lucerne

£1729

NEW FOR 2025

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Navigation App

FREE CASE OF WINE WITH BOOKING

VIEW TRIP

France

Cycling along the Atlantic Coast

£1839

NEW FOR 2025

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Navigation App

FREE CASE OF WINE WITH BOOKING

VIEW TRIP

Portugal : Mainland Portugal

Coimbra to Lisbon Cycling

£1989

NEW FOR 2025

VIEW TRIP

Self-guided cycling

11 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

FREE CASE OF WINE WITH BOOKING

VIEW TRIP

Norway

Cycling Norway's Fjords: Hardangerfjord from Bergen

£2619

NEW FOR 2025

VIEW TRIP

Self-guided cycling

5 nights,
hotel-to-hotel

Level: 2 & 3

Printed route
directions

FREE CASE OF WINE WITH BOOKING

VIEW TRIP

Canada : Sunshine Coast

Walk & Paddle Canada's Sunshine Coast

£2709

NEW FOR 2025

VIEW TRIP

Multi-activity holiday

8 nights,
hotel-to-hotel

Level: 1+ to 3

Headwater
Navigation App

FREE CASE OF WINE WITH BOOKING

VIEW TRIP

Norway

Cycling the Norwegian Archipelago South of Bergen

£2959

NEW FOR 2025

VIEW TRIP

Self-guided cycling

6 nights,
hotel-to-hotel

Level: 2 & 3

Printed route
directions

FREE CASE OF WINE WITH BOOKING

VIEW TRIP

Norway

Walking Norway's Fjords: Hardangerfjord from Bergen

£3259

NEW FOR 2025

VIEW TRIP

Self-guided walking

8 nights,
hotel-to-hotel

Level: 2 & 3

Printed route
directions

FREE CASE OF WINE WITH BOOKING

VIEW TRIP

Italy : Sicily

Walking the Highlights of Western Sicily

£1129

NEW FOR 2025

VIEW TRIP

Self-guided walking

7 nights,
twin centre

Level: 2
Moderate

Headwater
Navigation App

FREE CASE OF WINE WITH BOOKING

VIEW TRIP

France

Chateaux Of The Loire Walk

£1359


4.4 (7 reviews)

VIEW TRIP

Self-guided walking

7 nights,
hotel-to-hotel

Level: 1
Leisurely

Navigation App

FREE CASE OF WINE WITH BOOKING

VIEW TRIP

Italy : Veneto

Walking in the Venetian Hills

£1089


4.7 (90 reviews)

VIEW TRIP

Self-guided walking

8 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

FREE CASE OF WINE WITH BOOKING

VIEW TRIP

Italy : Sicily

Secrets of Sicily Cycling

£1259


4.6 (24 reviews)

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

FREE CASE OF WINE WITH BOOKING

VIEW TRIP

Italy : Veneto

Venetian Villas and Vineyards Cycling

£1319


4.7 (57 reviews)

VIEW TRIP

Self-guided cycling

8 nights,
hotel-to-hotel

Level: 1
Leisurely

Headwater
Navigation App

FREE CASE OF WINE WITH BOOKING

VIEW TRIP

Switzerland : The Bernese Oberland

Walking the Bernese Highlights West

£1489


4.5 (2 reviews)

VIEW TRIP

Self-guided walking

7 nights,
hotel-to-hotel

Level: 4
Challenging

Navigation App

FREE CASE OF WINE WITH BOOKING

VIEW TRIP

Switzerland : The Bernese Oberland

Walking the Bernese Highlights East

£1629


5.0 (3 reviews)

VIEW TRIP

Self-guided walking

7 nights,
hotel-to-hotel

Level: 3
Stretching

Navigation App

FREE CASE OF WINE WITH BOOKING

VIEW TRIP

Switzerland : Valais

Walking in Val D'Anniviers

£1649


4.5 (2 reviews)

VIEW TRIP

Self-guided walking

7 nights,
single centre

Level: 1 to 3

Headwater
Navigation App

FREE CASE OF WINE WITH BOOKING

VIEW TRIP

Slovenia

Julian Alps to the Adriatic Cycling

£2229


4.8 (126 reviews)

VIEW TRIP

Self-guided cycling

10 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

FREE CASE OF WINE WITH BOOKING

VIEW TRIP

United Kingdom : Northumberland

Walking the Best of Hadrian's Wall

£699


4.8 (29 reviews)

VIEW TRIP

Self-guided walking

5 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

FREE CASE OF WINE WITH BOOKING

VIEW TRIP

United Kingdom : Cornwall

Walking the Lizard Peninsula

£869


4.3 (3 reviews)

VIEW TRIP

Self-guided walking

5 nights,
hotel-to-hotel

Level: 2
Moderate

Printed route
directions

FREE CASE OF WINE WITH BOOKING

VIEW TRIP

United Kingdom : Cornwall

Walking Cornwall's North coast Padstow to Perranporth

£939

 
 

VIEW TRIP

Self-guided walking

5 nights,
hotel-to-hotel

Level: 2
Moderate

Printed route
directions

FREE CASE OF WINE WITH BOOKING

VIEW TRIP

United Kingdom : Lake District

Literary Walking in the Lake District

£1039


4.8 (36 reviews)

VIEW TRIP

Self-guided walking

6 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

FREE CASE OF WINE WITH BOOKING

VIEW TRIP

Switzerland : The Bernese Oberland

Classic Swiss Alps Walk

£1129


4.8 (153 reviews)

VIEW TRIP

Self-guided walking

7 nights,
single centre

Level: 2
Moderate

Headwater
Navigation App

FREE CASE OF WINE WITH BOOKING

VIEW TRIP

Ireland

Walking the Kerry Way and Killarney N.P.

£1139


4.9 (8 reviews)

VIEW TRIP

Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Navigation App

FREE CASE OF WINE WITH BOOKING

VIEW TRIP

Italy : Puglia

Contrasts of Puglia Cycling

£1449


4.6 (125 reviews)

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

FREE CASE OF WINE WITH BOOKING

VIEW TRIP

United Kingdom : Norfolk

Contrasts of Norfolk Cycling

£1549


5.0 (1 reviews)

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

FREE CASE OF WINE WITH BOOKING

VIEW TRIP

Portugal : Mainland Portugal

Porto Coastal Cycling

£1549


4.4 (59 reviews)

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1
Leisurely

Headwater
Navigation App

FREE CASE OF WINE WITH BOOKING

VIEW TRIP

Spain : Galicia

Walking the Camino de Santiago

£1949


4.6 (43 reviews)

VIEW TRIP

Self-guided pilgrimage

10 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

FREE CASE OF WINE WITH BOOKING

VIEW TRIP

Italy : Piedmont

Gastronomic Barolo Cycling by e-bike

£2169


4.8 (89 reviews)

VIEW TRIP

Self-guided cycling

8 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

FREE CASE OF WINE WITH BOOKING

VIEW TRIP

Portugal : Mainland Portugal

Walking the Green Coast of Minho

£589


4.0 (1 reviews)

VIEW TRIP

Self-guided walking

7 nights,
single centre

Level: 2
Moderate

Printed route
directions

FREE CASE OF WINE WITH BOOKING

VIEW TRIP

Spain : Catalonia

Catalan Classic Walk - Short Break

£659


4.7 (7 reviews)

VIEW TRIP

Self-guided walking

4 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

FREE CASE OF WINE WITH BOOKING

VIEW TRIP

Portugal : Mainland Portugal

Walking the Mountains, Valleys & Coast of Minho

£759


5.0 (3 reviews)

VIEW TRIP

Self-guided walking

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

FREE CASE OF WINE WITH BOOKING

VIEW TRIP

Ireland

Walking the Kerry Way and Killarney N.P. - Short Break

£789


4.0 (2 reviews)

VIEW TRIP

Self-guided walking

4 nights,
hotel-to-hotel

Level: 2
Moderate

Navigation App

FREE CASE OF WINE WITH BOOKING

VIEW TRIP

United Kingdom : Northern Ireland

Walking the Antrim Way

£829

 
 

VIEW TRIP

Self-guided walking

4 nights,
hotel-to-hotel

Level: 2
Moderate

Navigation App

FREE CASE OF WINE WITH BOOKING

VIEW TRIP

United Kingdom : Dorset

Jewels of the Jurassic Coast Walk

£849


4.3 (3 reviews)

VIEW TRIP

Self-guided walking

6 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

FREE CASE OF WINE WITH BOOKING

VIEW TRIP

Italy : Tuscany

Treasures of Tuscany Walk: San Gimignano to Volterra

£859

NEW FOR 2025

VIEW TRIP

Self-guided walking

7 nights,
twin centre

Level: 2+
Moderate plus

Headwater
Navigation App

FREE CASE OF WINE WITH BOOKING

VIEW TRIP

Portugal : Madeira

Walk the Garden Island of Madeira

£879


4.8 (4 reviews)

VIEW TRIP

Self-guided walking

7 nights,
single centre

Level: 2
Moderate

Headwater
Navigation App

FREE CASE OF WINE WITH BOOKING

VIEW TRIP

Romania : Transylvania

Transylvanian Castles Walk

£879


4.9 (20 reviews)

VIEW TRIP

Self-guided walking

7 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
Navigation App

FREE CASE OF WINE WITH BOOKING

VIEW TRIP

Spain : Catalonia

Contrasts of Catalunya Cycling - Short Break

£899


4.8 (8 reviews)

VIEW TRIP

Self-guided cycling

4 nights,
hotel-to-hotel

Level: 1
Leisurely

Headwater
Navigation App

FREE CASE OF WINE WITH BOOKING

VIEW TRIP

Switzerland : The Bernese Oberland

Walking in Kandersteg - Short Break

£919


4.9 (12 reviews)

VIEW TRIP

Self-guided walking

5 nights,
single centre

Level: 2
Moderate

Headwater
Navigation App

FREE CASE OF WINE WITH BOOKING

VIEW TRIP

Italy : Puglia

Undiscovered Puglia Walk - Discovering the South-East Coast

£939


4.8 (13 reviews)

VIEW TRIP

Self-guided walking

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

FREE CASE OF WINE WITH BOOKING

VIEW TRIP

Slovakia

Walking the Tatra Mountains in Slovakia

£959

NEW FOR 2025

VIEW TRIP

Self-guided walking

7 nights,
twin centre

Level: 2
Moderate

Headwater
Navigation App

FREE CASE OF WINE WITH BOOKING

VIEW TRIP

United Kingdom : Devon

Contrasts of Devon Walking

£979


4.5 (4 reviews)

VIEW TRIP

Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

FREE CASE OF WINE WITH BOOKING

VIEW TRIP

United Kingdom : Wales

Highlights of the Gower Peninsula Walk

£1049


5.0 (2 reviews)

VIEW TRIP

Self-guided walking

5 nights,
twin centre

Level: 1+
Leisurely plus

Headwater
Navigation App

FREE CASE OF WINE WITH BOOKING

VIEW TRIP

Czechia

Walking through Bohemia

£1049


4.9 (7 reviews)

VIEW TRIP

Self-guided walking

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

FREE CASE OF WINE WITH BOOKING

VIEW TRIP

United Kingdom : Devon

Walking South Devon's Coastal Path

£1049


5.0 (1 reviews)

VIEW TRIP

Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

FREE CASE OF WINE WITH BOOKING

VIEW TRIP

France : The Loire

Cycling The UNESCO Loire Valley

£1069


5.0 (4 reviews)

VIEW TRIP

Self-guided cycling

5 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Navigation App

FREE CASE OF WINE WITH BOOKING

VIEW TRIP

Italy : Sardinia

Walking Sardinia's Green Coast

£1079

NEW FOR 2025

VIEW TRIP

Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

FREE CASE OF WINE WITH BOOKING

VIEW TRIP

Italy : Italian Lakes

Cycling Lake Garda with e-bike

£1089


4.6 (5 reviews)

VIEW TRIP

Self-guided cycling

6 nights,
single centre

Level: 2+
Moderate plus

Headwater
Navigation App

FREE CASE OF WINE WITH BOOKING

VIEW TRIP

Andorra

Walk across Andorra

£1089


4.7 (7 reviews)

VIEW TRIP

Self-guided walking

7 nights,
hotel-to-hotel

Level: 4
Challenging

Headwater
Navigation App

FREE CASE OF WINE WITH BOOKING

VIEW TRIP

France : The Loire

Multi Activity in the Loire

£1099


5.0 (2 reviews)

VIEW TRIP

Multi-activity holiday

5 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Navigation App

FREE CASE OF WINE WITH BOOKING

VIEW TRIP

United Kingdom : Wales

Walk the Welsh Highland Railway

£1119


3.7 (3 reviews)

VIEW TRIP

Self-guided walking

6 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

FREE CASE OF WINE WITH BOOKING

VIEW TRIP

France : Mont Blanc

Mont Blanc Walks - Short Break Premium

£1129

 
 

VIEW TRIP

Self-guided walking

4 nights,
single centre

Level: 2+
Moderate plus

Headwater
Navigation App

FREE CASE OF WINE WITH BOOKING

VIEW TRIP

United Kingdom : Cornwall

Walking the Western Tip of Cornwall

£1149


4.9 (18 reviews)

VIEW TRIP

Self-guided walking

6 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Printed route
directions

FREE CASE OF WINE WITH BOOKING

VIEW TRIP

Switzerland : Davos

Walk the Crossroads of Five Passes

£1149


4.9 (8 reviews)

VIEW TRIP

Self-guided walking

7 nights,
single centre

Level: 1 to 3

Headwater
Navigation App

FREE CASE OF WINE WITH BOOKING

VIEW TRIP

France : Normandy

D-Day Beaches Of Normandy Cycling

£1199


4.6 (7 reviews)

VIEW TRIP

Self-guided cycling

5 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Printed route
directions

FREE CASE OF WINE WITH BOOKING

VIEW TRIP

Portugal : Mainland Portugal

Tour the Treasures of Portugal

£1199


4.8 (5 reviews)

VIEW TRIP

Self-guided cultural tour

7 nights,
twin centre



FREE CASE OF WINE WITH BOOKING

VIEW TRIP

France : Normandy

Normandy Walk from Deauville to Bayeux

£1219


4.7 (6 reviews)

VIEW TRIP

Self-guided walking

7 nights,
hotel-to-hotel

Level: 1
Leisurely

Printed route
directions

FREE CASE OF WINE WITH BOOKING

VIEW TRIP

Ireland

Walking and Cycling the Wild Atlantic Way

£1229

 
 

VIEW TRIP

Multi-activity holiday

7 nights,
hotel-to-hotel

Level: 2
Moderate

Navigation App

FREE CASE OF WINE WITH BOOKING

VIEW TRIP

France : Burgundy

Walking in Burgundy's Vineyards

£1279


4.8 (8 reviews)

VIEW TRIP

Self-guided walking

6 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

FREE CASE OF WINE WITH BOOKING

VIEW TRIP

United Kingdom : Norfolk

Highlights of Norfolk Cycling

£1289


4.4 (11 reviews)

VIEW TRIP

Self-guided cycling

5 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

FREE CASE OF WINE WITH BOOKING

VIEW TRIP

France : The Dordogne

Canoeing on the Dordogne

£1299


4.9 (60 reviews)

VIEW TRIP

8 nights,
hotel-to-hotel

Printed route
directions



FREE CASE OF WINE WITH BOOKING

VIEW TRIP

United Kingdom : Wales

Walking Offa's Dyke Path (South)

£1299

 
 

VIEW TRIP

Self-guided walking

8 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
Navigation App

FREE CASE OF WINE WITH BOOKING

VIEW TRIP

France : Burgundy

Cycling the Vineyards From Beaune to Macon

£1329


4.8 (6 reviews)

VIEW TRIP

Self-guided cycling

6 nights,
hotel-to-hotel

Level: 1
Leisurely

Printed route
directions

FREE CASE OF WINE WITH BOOKING

VIEW TRIP

France : Canal du Midi

Canal du midi Cycling : from Toulouse to Sete

£1329


4.8 (5 reviews)

VIEW TRIP

Self-guided cycling

6 nights,
hotel-to-hotel

Level: 2
Moderate

Navigation App

FREE CASE OF WINE WITH BOOKING

VIEW TRIP

Montenegro

Highlights of Southern Montenegro Walk

£1329


5.0 (1 reviews)

VIEW TRIP

Self-guided walking

7 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
Navigation App

FREE CASE OF WINE WITH BOOKING

VIEW TRIP

France : The Loire

Canoeing on the Loire

£1339


4.0 (1 reviews)

VIEW TRIP

5 nights,
hotel-to-hotel

Navigation App



FREE CASE OF WINE WITH BOOKING

VIEW TRIP

France : The Loire

Cycling The Chateaux Of The Loire - Upgraded Short

£1339


4.8 (4 reviews)

VIEW TRIP

Self-guided cycling

5 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Navigation App

FREE CASE OF WINE WITH BOOKING

VIEW TRIP

Portugal : The Algarve

Cycling the Algarve's Rota Vicentina

£1419


4.9 (9 reviews)

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
Navigation App

FREE CASE OF WINE WITH BOOKING

VIEW TRIP

Portugal : Mainland Portugal

Walk the Highlights of Northern Portugal

£1429


4.5 (6 reviews)

VIEW TRIP

Self-guided walking

8 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
Navigation App

FREE CASE OF WINE WITH BOOKING

VIEW TRIP

Italy : Tuscany

Cycling the hills of San Gimignano by E-bike

£1459

NEW FOR 2025

VIEW TRIP

Self-guided cycling

7 nights,
single centre

Level: 2+ & 3

Headwater
Navigation App

FREE CASE OF WINE WITH BOOKING

VIEW TRIP

Croatia

Hike, Bike & Paddle Croatia

£1479

NEW FOR 2025

VIEW TRIP

Multi-activity holiday

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

FREE CASE OF WINE WITH BOOKING

VIEW TRIP

Portugal : Mainland Portugal

Portugal Coastal Way to Santiago

£1479


5.0 (11 reviews)

VIEW TRIP

Self-guided pilgrimage

14 nights,
hotel-to-hotel

Level: 2
Moderate

Printed route
directions

FREE CASE OF WINE WITH BOOKING

VIEW TRIP

Portugal : Mainland Portugal

Cycling in Portugal: From the Mountains to the Sea

£1529


4.5 (17 reviews)

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

FREE CASE OF WINE WITH BOOKING

VIEW TRIP

United Kingdom : Wales

Walking Offa's Dyke Path (North)

£1629

 
 

VIEW TRIP

Self-guided walking

9 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
Navigation App

FREE CASE OF WINE WITH BOOKING

VIEW TRIP

Norway

Walking in Balestrand

£1639


4.6 (5 reviews)

VIEW TRIP

Self-guided walking

7 nights,
hotel-to-hotel

Level: 1 to 3

Headwater
Navigation App

FREE CASE OF WINE WITH BOOKING

VIEW TRIP

United Kingdom : The Cotswolds

Best of the Cotswolds Cycling

£1709


4.0 (1 reviews)

VIEW TRIP

Self-guided cycling

6 nights,
twin centre

Level: 2
Moderate

Headwater
Navigation App

FREE CASE OF WINE WITH BOOKING

VIEW TRIP

France : Normandy

Paris to the Sea Along the Seine River

£1819

NEW FOR 2025

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Printed route
directions

FREE CASE OF WINE WITH BOOKING

VIEW TRIP

Portugal : Mainland Portugal

Porto to Coimbra Cycling

£1829


4.8 (56 reviews)

VIEW TRIP

Self-guided cycling

9 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

FREE CASE OF WINE WITH BOOKING

VIEW TRIP

Denmark

Nordic Cities by Rail

£1829

NEW FOR 2025

VIEW TRIP

Self-guided cultural tour

9 nights,
hotel-to-hotel



FREE CASE OF WINE WITH BOOKING

VIEW TRIP

Slovenia

Secrets of Slovenia Cycling

£1849


4.9 (14 reviews)

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
Navigation App

FREE CASE OF WINE WITH BOOKING

VIEW TRIP

France : Mont Blanc

Walking Tour du Mont Blanc - Premium

£1899


4.8 (5 reviews)

VIEW TRIP

Self-guided walking

7 nights,
twin centre

Level: 3
Stretching

Headwater
Navigation App

FREE CASE OF WINE WITH BOOKING

VIEW TRIP

Iceland

Walking Iceland's Diamond Circle

£2509

NEW FOR 2025

VIEW TRIP

Self-guided walking

7 nights,
hotel-to-hotel

Level: 1 to 3

Headwater
Navigation App

FREE CASE OF WINE WITH BOOKING

VIEW TRIP

Canada : Sunshine Coast

Walking Canada's Sunshine Coast

£2609


4.7 (3 reviews)

VIEW TRIP

Self-guided walking

8 nights,
hotel-to-hotel

Level: 1 to 3

Headwater
Navigation App

FREE CASE OF WINE WITH BOOKING

VIEW TRIP

USA : Maine

Cycling Maine's Coast & National Park

£3199

 
 

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
Navigation App

FREE CASE OF WINE WITH BOOKING

VIEW TRIP

Japan

Walk the Nakasendo Trail

£3399

 
 

VIEW TRIP

Self-guided walking

10 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Printed route
directions

FREE CASE OF WINE WITH BOOKING

VIEW TRIP

Faroe Islands

Walking the Faroe Islands - With Private Guide

£3779

NEW FOR 2025

VIEW TRIP

Private guided walking

7 nights,
single centre

Level: 2+
Moderate plus

FREE CASE OF WINE WITH BOOKING

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
  • Albania
  • Andorra
  • Austria
  • Belgium
  • Bermuda
  • Bosnia
  • Canada
  • Cape Verde
  • China
  • Costa Rica
  • Croatia
  • Cyprus
  • Czechia
  • Denmark
  • Egypt
  • Estonia
  • Finland
  • Faroe Islands
  • Germany
  • Greece
  • Holland
  • Iceland
  • Ireland
  • Japan
  • Kenya
  • Malta
  • Montenegro
  • Morocco
  • Nepal
  • Norway
  • Peru
  • Romania
  • Slovakia
  • Slovenia
  • South Africa
  • Sri Lanka
  • Sweden
  • Switzerland
  • Thailand
  • USA
  • Vietnam

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