Holidays with the Headwater Navigation App

Showing 172 out of 338 trips

We offer GPS route navigation on many of our walking and cycling holidays so even if you have no map reading skills - you won't get lost with Headwater!

The Headwater Navigation App provides our comprehensively researched and carefully checked routes in an easy to use and convenient format, with easy-to-follow turn-by-turn instructions all along your route.

Listed below are the holidays that feature the app, to view any of the holidays shown simply click on the 'View holiday' button. To refine your search use the panel above to select the activity type, country, departure months, etc.

Gozo

Walking on Glorious Gozo - Short Break

£459

NEW FOR 2025

VIEW TRIP

Self-guided walking

4 nights,
single centre

Level: 1+
Leisurely plus

Headwater
Navigation App

VIEW TRIP

Malta

Highlights of Secrets of Malta Walking

£489

 
 

VIEW TRIP

Self-guided walking

4 nights,
single centre

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

United Kingdom : The Channel Islands

Walking in Jersey Premium

£629

NEW FOR 2025

VIEW TRIP

Self-guided walking

3 nights,
single centre

Level: 1+ & 2

Headwater
Navigation App

VIEW TRIP

Gozo

Walking on Glorious Gozo

£629

NEW FOR 2025

VIEW TRIP

Self-guided walking

7 nights,
single centre

Level: 1+
Leisurely plus

Headwater
Navigation App

VIEW TRIP

Malta

Discovering the Maltese Islands

£709


4.1 (7 reviews)

VIEW TRIP

Self-guided walking

7 nights,
twin centre

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

Spain : The Canary Islands

Walking the trails of Tenerife

£779

 
 

VIEW TRIP

Self-guided walking

7 nights,
single centre

Level: 2 & 3

Headwater
Navigation App

VIEW TRIP

Spain : Andalucia

Walking in Sierra de Aracena

£849


4.8 (10 reviews)

VIEW TRIP

Self-guided walking

7 nights,
hotel-to-hotel

Level: 1
Leisurely

Headwater
Navigation App

VIEW TRIP

Portugal : Madeira

Walking the Waterways and villages of Madeira

£899


4.0 (5 reviews)

VIEW TRIP

Self-guided walking

7 nights,
single centre

Level: 2+
Moderate plus

Headwater
Navigation App

VIEW TRIP

Italy : Puglia

Cycling the Heel of Italy - Alberobello to Lecce

£909


4.7 (40 reviews)

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

Denmark

Cycling from Copenhagen

£929


5.0 (1 reviews)

VIEW TRIP

Self-guided cycling

4 nights,
single centre

Level: 1
Leisurely

Headwater
Navigation App

VIEW TRIP

Portugal : The Azores

Walking the Green Island of the Azores

£929


5.0 (1 reviews)

VIEW TRIP

Self-guided walking

7 nights,
single centre

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

Spain : The Canary Islands

Contrasts of Lanzarote

£939


5.0 (2 reviews)

VIEW TRIP

Self-guided walking

7 nights,
single centre

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

Spain : The Canary Islands

Contrasts of La Gomera

£949


4.3 (4 reviews)

VIEW TRIP

Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

Italy : Umbria

Undiscovered Villages of Umbria Walk

£969


4.8 (11 reviews)

VIEW TRIP

Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

Spain : The Canary Islands

Volcanoes and Vineyards of Lanzarote

£979


4.4 (7 reviews)

VIEW TRIP

Self-guided walking

7 nights,
hotel-to-hotel

Level: 1 to 2+

Headwater
Navigation App

VIEW TRIP

Spain : The Canary Islands

Walking on Gran Canaria

£989


5.0 (5 reviews)

VIEW TRIP

Self-guided walking

7 nights,
twin centre

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

Spain : The Canary Islands

Walking in Fuerteventura along the GR 131

£1039

NEW FOR 2025

VIEW TRIP

Self-guided walking

7 nights,
hotel-to-hotel

Level: 2 & 2+

Headwater
Navigation App

VIEW TRIP

Italy : The Bay of Naples

The Islands of Amalfi Walk

£1059


4.6 (12 reviews)

VIEW TRIP

Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

Albania

E-bike Across Southern Albania

£1089

NEW FOR 2025

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
Navigation App

VIEW TRIP

Italy : Umbria

The Wine Trails of Umbria Cycling

£1129


5.0 (1 reviews)

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

Croatia

Dalmatian Coast Island Hopping

£1129


4.8 (13 reviews)

VIEW TRIP

Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

Portugal : The Algarve

Walking Rota Vicentina North Fishermen's Trail

£1239

 
 

VIEW TRIP

Self-guided walking

8 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

Greece

Cycling in the Peloponnese

£1259


4.8 (11 reviews)

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

Italy : Italian Lakes

Walking at Lakes Orta and Maggiore

£1379

NEW FOR 2025

VIEW TRIP

Self-guided walking

8 nights,
hotel-to-hotel

Level: 1+ & 2

Headwater
Navigation App

VIEW TRIP

United Kingdom : The Channel Islands

Cycling in Jersey, Guernsey and Sark

£1389


4.0 (1 reviews)

VIEW TRIP

Self-guided cycling

6 nights,
twin centre

Level: 1+
Leisurely plus

Headwater
Navigation App

VIEW TRIP

Portugal : Mainland Portugal

Cycling in the Douro Valley

£1419

 
 

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 3
Stretching

Headwater
Navigation App

VIEW TRIP

Italy : Puglia

Cycling the Heel of Italy - Matera to Lecce

£1459


4.6 (10 reviews)

VIEW TRIP

Self-guided cycling

11 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

Spain : The Canary Islands

Walking in Tenerife and La Palma

£1509

 
 

VIEW TRIP

Self-guided walking

7 nights,
twin centre

Level: 3
Stretching

Headwater
Navigation App

VIEW TRIP

Spain : The Canary Islands

Contrasts of Tenerife Walk (with transfers)

£1849

 
 

VIEW TRIP

Self-guided walking

7 nights,
twin centre

Level: 1+ to 2+

Headwater
Navigation App

VIEW TRIP

Portugal : Mainland Portugal

Coimbra to Lisbon Cycling

£1889

NEW FOR 2025

VIEW TRIP

Self-guided cycling

11 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

VIEW TRIP

Canada : Sunshine Coast

Walk & Paddle Canada’s Sunshine Coast

£2609

NEW FOR 2025

VIEW TRIP

Multi-activity holiday

8 nights,
hotel-to-hotel

Level: 1+ to 3

Headwater
Navigation App

VIEW TRIP

Italy : Sicily

Walking the Highlights of Western Sicily

£999

NEW FOR 2025

VIEW TRIP

Self-guided walking

7 nights,
twin centre

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

Italy : The Bay of Naples

The Amalfi Coast Walk

£2009


4.8 (87 reviews)

VIEW TRIP

Self-guided walking

8 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

Italy : Sicily

Volcanoes of Sicily Walk

£1359


4.4 (11 reviews)

VIEW TRIP

Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

Gozo

Walking on Gozo - Calypso's Isle

£749


4.6 (141 reviews)

VIEW TRIP

Self-guided walking

7 nights,
single centre

Level: 1+
Leisurely plus

Headwater
Navigation App

VIEW TRIP

Spain : The Canary Islands

Contrasts of Tenerife Walk (with car hire)

£1169


4.7 (11 reviews)

VIEW TRIP

Self-guided walking

7 nights,
twin centre

Level: 1+ to 2+

Headwater
Navigation App

VIEW TRIP

Italy : The Bay of Naples

Paths of the Amalfi Coast

£729


4.6 (28 reviews)

VIEW TRIP

Self-guided walking

7 nights,
single centre

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

Italy : The Bay of Naples

Walking Amalfi's Path of the Gods

£799


5.0 (2 reviews)

VIEW TRIP

Self-guided walking

7 nights,
single centre

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

Italy : Veneto

Walking in the Venetian Hills

£849


4.7 (88 reviews)

VIEW TRIP

Self-guided walking

8 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

VIEW TRIP

Italy : Veneto

Heart of Veneto Cycling

£939


4.8 (72 reviews)

VIEW TRIP

Self-guided cycling

7 nights,
single centre

Level: 1
Leisurely

Headwater
Navigation App

VIEW TRIP

Italy : Puglia

Self Guided Walking in Puglia: From Lecce to Matera

£1009


4.7 (49 reviews)

VIEW TRIP

Self-guided walking

7 nights,
hotel-to-hotel

Level: 1
Leisurely

Headwater
Navigation App

VIEW TRIP

Italy : Veneto

Venetian Villas and Vineyards Cycling

£1079


4.7 (57 reviews)

VIEW TRIP

Self-guided cycling

8 nights,
hotel-to-hotel

Level: 1
Leisurely

Headwater
Navigation App

VIEW TRIP

Italy : Sicily

Secrets of Sicily Cycling

£1159


4.6 (22 reviews)

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

VIEW TRIP

Italy : Tuscany

A Taste of Tuscany Walking

£1169


4.9 (28 reviews)

VIEW TRIP

Self-guided walking

7 nights,
single centre

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

Italy : Tuscany

A Taste of Tuscany Cycling

£1219


4.9 (27 reviews)

VIEW TRIP

Self-guided cycling

7 nights,
single centre

Level: 2+
Moderate plus

Headwater
Navigation App

VIEW TRIP

Portugal : Madeira

Marvels of Madeira Walk

£1219


4.7 (119 reviews)

VIEW TRIP

Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

Portugal : The Algarve

Cycling in The Real Algarve

£1279


4.7 (61 reviews)

VIEW TRIP

Self-guided cycling

6 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

Bermuda

Islands of Bermuda Walk

£1279


4.6 (34 reviews)

VIEW TRIP

Self-guided walking

7 nights,
single centre

Level: 1
Leisurely

Headwater
Navigation App

VIEW TRIP

Italy : The Dolomites

Walks in The Italian Dolomites

£1319


4.9 (126 reviews)

VIEW TRIP

Self-guided walking

7 nights,
single centre

Level: 2+
Moderate plus

Headwater
Navigation App

VIEW TRIP

France : Provence

Landscapes of the Luberon Walk

£1379


4.7 (37 reviews)

VIEW TRIP

Self-guided walking

8 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

VIEW TRIP

Italy : Sicily

Cycling through Baroque Sicily

£1479


4.4 (20 reviews)

VIEW TRIP

Self-guided cycling

8 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

Italy : The Dolomites

Walking the Dolomites of Alta Badia

£1479


4.8 (23 reviews)

VIEW TRIP

Self-guided walking

7 nights,
single centre

Level: 2+
Moderate plus

Headwater
Navigation App

VIEW TRIP

France : Provence

Cotes du Ventoux Cycling

£1729


4.8 (36 reviews)

VIEW TRIP

Self-guided cycling

6 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

VIEW TRIP

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

VIEW TRIP

France : Provence

Landscapes of the Luberon Cycling

£2039


4.4 (21 reviews)

VIEW TRIP

Self-guided cycling

8 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

Spain : Catalonia

Catalan Classic Walk

£819


4.7 (78 reviews)

VIEW TRIP

Self-guided walking

6 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

VIEW TRIP

Portugal : The Algarve

Walk the Algarve's Wild West

£1049


4.8 (86 reviews)

VIEW TRIP

Self-guided walking

6 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

VIEW TRIP

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

VIEW TRIP

Spain : Catalonia

Contrasts of Catalunya Cycling

£1079


4.7 (53 reviews)

VIEW TRIP

Self-guided cycling

6 nights,
hotel-to-hotel

Level: 1
Leisurely

Headwater
Navigation App

VIEW TRIP

Austria : Salzburg

Austrian Lakes Activities

£1079


4.8 (68 reviews)

VIEW TRIP

Multi-activity holiday

7 nights,
single centre

Level: 1
Leisurely

Headwater
Navigation App

VIEW TRIP

France : The Dordogne

Dordogne River Walk

£1099


4.7 (29 reviews)

VIEW TRIP

Self-guided walking

8 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

Spain : Balearic Islands

Cycling in Mallorca: Coast to Coast

£1179


4.7 (25 reviews)

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

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

VIEW TRIP

Switzerland : The Bernese Oberland

Classic Swiss Alps Walk

£1299


4.8 (134 reviews)

VIEW TRIP

Self-guided walking

7 nights,
single centre

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

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

VIEW TRIP

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

VIEW TRIP

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

VIEW TRIP

United Kingdom : Lake District

Literary Walking in the Lake District

£1399


4.8 (32 reviews)

VIEW TRIP

Self-guided walking

6 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

VIEW TRIP

Portugal : Mainland Portugal

Porto Coastal Cycling

£1449


4.4 (59 reviews)

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1
Leisurely

Headwater
Navigation App

VIEW TRIP

Croatia

Coastal Croatia - Porec to Pula Cycling

£1479


4.7 (85 reviews)

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

VIEW TRIP

United Kingdom : The Cotswolds

Best of the Cotswolds Walk

£1579


4.8 (13 reviews)

VIEW TRIP

Self-guided walking

8 nights,
hotel-to-hotel

Level: 1
Leisurely

Printed route
directions

VIEW TRIP

Spain : Galicia

Walking the Camino de Santiago

£1749


4.6 (43 reviews)

VIEW TRIP

Self-guided pilgrimage

10 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

Italy : Piedmont

Gastronomic Barolo Walk

£1909


4.9 (91 reviews)

VIEW TRIP

Self-guided walking

8 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

Italy : Piedmont

Gastronomic Barolo Cycling by e-bike

£2299


4.8 (88 reviews)

VIEW TRIP

Self-guided cycling

8 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
Navigation App

VIEW TRIP

Sweden : sweden

Cycling from Stockholm

£60

 
 

VIEW TRIP

Self-guided cycling

5 nights,
single centre

Level: 1+
Leisurely plus

Headwater
Navigation App

VIEW TRIP

Portugal

Walk the Garden Island of Madeira

£419


4.7 (3 reviews)

VIEW TRIP

Self-guided walking

7 nights,
single centre

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

Spain : Andalucia

Hidden Valleys of Cordoba Walk

£469


4.8 (51 reviews)

VIEW TRIP

Self-guided walking

7 nights,
single centre

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

Gozo

Walking on Gozo - Calypso's Isle - Short Break

£489


4.8 (9 reviews)

VIEW TRIP

Self-guided walking

4 nights,
single centre

Level: 1+
Leisurely plus

Headwater
Navigation App

VIEW TRIP

Cyprus

WALKING THE AKAMAS PENINSULA

£619


4.5 (11 reviews)

VIEW TRIP

Self-guided walking

7 nights,
twin centre

Level: 1 & 2

Headwater
Navigation App

VIEW TRIP

United Kingdom : Devon

Walking Devon's Coastal Highlights

£629


4.0 (1 reviews)

VIEW TRIP

Self-guided walking

4 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

Malta

Secrets of Malta Walking

£659


5.0 (3 reviews)

VIEW TRIP

Self-guided walking

7 nights,
single centre

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

Andorra

Walking the Rugged Pyrenees of Andorra

£659


4.0 (2 reviews)

VIEW TRIP

Self-guided walking

7 nights,
twin centre

Level: 4
Challenging

Headwater
Navigation App

VIEW TRIP

Spain : Andalucia

Walking the White Villages of the Alpujarras

£709


4.5 (6 reviews)

VIEW TRIP

Self-guided walking

7 nights,
hotel-to-hotel

Level: 2 & 2+

Headwater
Navigation App

VIEW TRIP

Spain : Asturias

Highlights of the Picos de Europa

£719


4.3 (6 reviews)

VIEW TRIP

Self-guided walking

7 nights,
single centre

Level: 3
Stretching

Headwater
Navigation App

VIEW TRIP

Italy : Tuscany

Treasures of Tuscany Walk: San Gimignano to Volterra

£719

NEW FOR 2025

VIEW TRIP

Self-guided walking

7 nights,
twin centre

Level: 2+
Moderate plus

Headwater
Navigation App

VIEW TRIP

Greece

Walking on Kythnos Island

£739


5.0 (2 reviews)

VIEW TRIP

Self-guided walking

6 nights,
twin centre

Level: 2+
Moderate plus

Headwater
Navigation App

VIEW TRIP

Romania : Transylvania

Transylvanian Castles Walk

£749


5.0 (7 reviews)

VIEW TRIP

Self-guided walking

7 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
Navigation App

VIEW TRIP

Cyprus

Contrasts of Cyprus Walking

£759


4.6 (7 reviews)

VIEW TRIP

Self-guided walking

7 nights,
hotel-to-hotel

Level: 1+ to 2+

Headwater
Navigation App

VIEW TRIP

United Kingdom : Dorset

Jewels of the Jurassic Coast Walk

£789


4.3 (3 reviews)

VIEW TRIP

Self-guided walking

6 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

VIEW TRIP

Switzerland : Valais

Walking the Valais Matterhorn Region

£799

 
 

VIEW TRIP

Self-guided walking

7 nights,
twin centre

Level: 2+ & 3

Headwater
Navigation App

VIEW TRIP

Spain : Balearic Islands

Walking the Coastal Trails of Menorca

£809


4.6 (60 reviews)

VIEW TRIP

Self-guided walking

7 nights,
single centre

Level: 1
Leisurely

Headwater
Navigation App

VIEW TRIP

Spain : Balearic Islands

Walking Mallorca's Mountains and Coast

£819


3.3 (4 reviews)

VIEW TRIP

Self-guided walking

7 nights,
single centre

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

Italy : Puglia

Undiscovered Puglia Walk - Discovering the South-East Coast

£829


4.6 (7 reviews)

VIEW TRIP

Self-guided walking

7 nights,
hotel-to-hotel

Level: 1
Leisurely

Headwater
Navigation App

VIEW TRIP

Spain : Catalonia

Catalonia Activities

£839


4.5 (13 reviews)

VIEW TRIP

Multi-activity holiday

7 nights,
single centre

Level: 1
Leisurely

Headwater
Navigation App

VIEW TRIP

France : Alsace

Villages & Vineyards of Alsace- Short Break

£839


5.0 (2 reviews)

VIEW TRIP

Self-guided walking

4 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

Spain : Catalonia

Catalan Classic Walk - Short Break

£849


4.7 (7 reviews)

VIEW TRIP

Self-guided walking

4 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

VIEW TRIP

United Kingdom : Devon

Contrasts of Devon Walking

£859


4.7 (3 reviews)

VIEW TRIP

Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

Spain : The Canary Islands

Walking the Trails of La Palma

£899


4.3 (8 reviews)

VIEW TRIP

Self-guided walking

7 nights,
hotel-to-hotel

Level: 3
Stretching

Headwater
Navigation App

VIEW TRIP

Italy : Italian Lakes

Cycling Lake Garda with e-bike

£929


4.5 (2 reviews)

VIEW TRIP

Self-guided cycling

6 nights,
single centre

Level: 2+
Moderate plus

Headwater
Navigation App

VIEW TRIP

Italy : Sardinia

Walking Sardinia's Green Coast

£929

NEW FOR 2025

VIEW TRIP

Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

France : Burgundy

Walking in Burgundy’s Vineyards - Short Break

£939

 
 

VIEW TRIP

Self-guided walking

4 nights,
hotel-to-hotel

Level: 1
Leisurely

Headwater
Navigation App

VIEW TRIP

Spain : The Canary Islands

Highlights of El Hierro Walk

£959


4.9 (10 reviews)

VIEW TRIP

Self-guided walking

7 nights,
hotel-to-hotel

Level: 2+ & 3

Headwater
Navigation App

VIEW TRIP

Austria : The Tyrol

Alpine Walks in the Stubai Valley

£969


4.6 (11 reviews)

VIEW TRIP

Self-guided walking

7 nights,
single centre

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

Austria : The Tyrol

Walking the Tyrolean Mountains

£989


5.0 (1 reviews)

VIEW TRIP

Self-guided walking

6 nights,
single centre

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

Andorra

Walk across Andorra

£989


4.6 (5 reviews)

VIEW TRIP

Self-guided walking

7 nights,
hotel-to-hotel

Level: 4
Challenging

Headwater
Navigation App

VIEW TRIP

United Kingdom : Wales

Highlights of the Gower Peninsula Walk

£1009


5.0 (2 reviews)

VIEW TRIP

Self-guided walking

5 nights,
twin centre

Level: 1+
Leisurely plus

Headwater
Navigation App

VIEW TRIP

United Kingdom : Devon

Walking South Devon's Coastal Path

£1019


5.0 (1 reviews)

VIEW TRIP

Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

Italy : Campania

Coastal Cilento Walk

£1019


4.8 (5 reviews)

VIEW TRIP

Self-guided walking

8 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
Navigation App

VIEW TRIP

Italy : The Bay of Naples

Gems of the Amalfi Coast Walking

£1029


4.7 (3 reviews)

VIEW TRIP

Self-guided walking

7 nights,
twin centre

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

France : Mont Blanc

Mont Blanc Walks – Short Break

£1049

 
 

VIEW TRIP

Self-guided walking

4 nights,
single centre

Level: 2+
Moderate plus

Headwater
Navigation App

VIEW TRIP

Switzerland : The Bernese Oberland

Walking in Kandersteg - Short Break

£1049


4.9 (12 reviews)

VIEW TRIP

Self-guided walking

5 nights,
single centre

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

Switzerland : The Bernese Oberland

Walk the Crossroads of Five Passes

£1049


4.8 (5 reviews)

VIEW TRIP

Self-guided walking

7 nights,
single centre

Level: 1 to 3

Headwater
Navigation App

VIEW TRIP

Austria : Lake Constance

Highlights of Lake Constance by bike

£1059


4.9 (26 reviews)

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1
Leisurely

Headwater
Navigation App

VIEW TRIP

Spain : Catalonia

Classic Catalan Cycling

£1059


4.8 (11 reviews)

VIEW TRIP

Self-guided cycling

8 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

United Kingdom : The Channel Islands

Walking in Jersey, Guernsey and Sark

£1059


4.4 (14 reviews)

VIEW TRIP

Self-guided walking

6 nights,
twin centre

Level: 1+ & 2

Headwater
Navigation App

VIEW TRIP

United Kingdom : Wales

Walk the Welsh Highland Railway

£1079


3.7 (3 reviews)

VIEW TRIP

Self-guided walking

6 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

Italy : Umbria

Walking on the Francigena Way

£1079


4.6 (11 reviews)

VIEW TRIP

Self-guided pilgrimage

9 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
Navigation App

VIEW TRIP

Bosnia

Walking the Olympic Mountains of Bosnia

£1089

NEW FOR 2025

VIEW TRIP

Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

Spain : Galicia

Highlights of the Camino de Santiago Walk

£1109


4.9 (16 reviews)

VIEW TRIP

Self-guided pilgrimage

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

Greece

Cycling the Coast of Eastern Crete

£1119


4.0 (2 reviews)

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 3
Stretching

Headwater
Navigation App

VIEW TRIP

Spain : Valencia

Cycling Valencia and the Orange Blossom Coast

£1149


4.5 (8 reviews)

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

France : Burgundy

Walking in Burgundy’s Vineyards

£1149


4.7 (6 reviews)

VIEW TRIP

Self-guided walking

6 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

VIEW TRIP

Greece : Peloponnese

Walking the Historical Paths of Outer Mani

£1149

NEW FOR 2025

VIEW TRIP

Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

France : Mont Blanc

Mont Blanc Walks – Short Break Premium

£1169

 
 

VIEW TRIP

Self-guided walking

4 nights,
single centre

Level: 2+
Moderate plus

Headwater
Navigation App

VIEW TRIP

Spain : Andalucia

E-biking in Andalucia: Sierra de Aracena

£1179

NEW FOR 2025

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

VIEW TRIP

United Kingdom : Wales

Walking Offa's Dyke Path (South)

£1199

 
 

VIEW TRIP

Self-guided walking

8 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
Navigation App

VIEW TRIP

Croatia

Hike, Bike & Paddle Croatia

£1209

NEW FOR 2025

VIEW TRIP

Multi-activity holiday

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

VIEW TRIP

Greece : Peloponnese

Peloponnese Coast and Mountain Walking

£1209

NEW FOR 2025

VIEW TRIP

Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

France : Provence

Hilltop Villages of Provence Cycling

£1229


4.8 (16 reviews)

VIEW TRIP

Self-guided cycling

6 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
Navigation App

VIEW TRIP

Greece

Walking on Kythnos Island - Premium

£1259


4.6 (7 reviews)

VIEW TRIP

Self-guided walking

6 nights,
twin centre

Level: 2+
Moderate plus

Headwater
Navigation App

VIEW TRIP

Portugal : Mainland Portugal

Walk the Highlights of Northern Portugal

£1269


4.5 (6 reviews)

VIEW TRIP

Self-guided walking

8 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
Navigation App

VIEW TRIP

Spain : Rioja

Vineyards of La Rioja Cycling

£1279


4.6 (7 reviews)

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

France : Alsace

Villages & Vineyards of Alsace

£1279


4.4 (7 reviews)

VIEW TRIP

Self-guided walking

6 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

Sweden : sweden

Cycling Stockholm's Archipelago

£1289


5.0 (1 reviews)

VIEW TRIP

Self-guided cycling

6 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

VIEW TRIP

Portugal : The Algarve

Cycling the Algarve's Rota Vicentina

£1289


4.9 (8 reviews)

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
Navigation App

VIEW TRIP

France : The Dordogne

Dordogne Activities

£1289


4.8 (31 reviews)

VIEW TRIP

Multi-activity holiday

8 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

Spain : Catalonia

Contrasts of Catalunya Cycling - Short Break

£1319


4.6 (5 reviews)

VIEW TRIP

Self-guided cycling

4 nights,
hotel-to-hotel

Level: 1
Leisurely

Headwater
Navigation App

VIEW TRIP

Norway

Walking in Balestrand

£1339


4.7 (3 reviews)

VIEW TRIP

Self-guided walking

7 nights,
hotel-to-hotel

Level: 1 to 3

Headwater
Navigation App

VIEW TRIP

Italy : Italian Lakes

Cycling the Italian Lakes

£1349


4.0 (1 reviews)

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

Montenegro

Highlights of Southern Montenegro Walk

£1349


5.0 (1 reviews)

VIEW TRIP

Self-guided walking

7 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
Navigation App

VIEW TRIP

Italy : Tuscany

Cycling the hills of San Gimignano by E-bike

£1359

NEW FOR 2025

VIEW TRIP

Self-guided cycling

7 nights,
single centre

Level: 2+ & 3

Headwater
Navigation App

VIEW TRIP

Spain : The Canary Islands

Walking in El Hierro

£1359


5.0 (1 reviews)

VIEW TRIP

Self-guided walking

7 nights,
single centre

Level: 1 to 2+

Headwater
Navigation App

VIEW TRIP

Portugal : The Azores

Azores By E-bike

£1369


4.0 (4 reviews)

VIEW TRIP

Self-guided cycling

6 nights,
hotel-to-hotel

Level: 3
Stretching

Headwater
Navigation App

VIEW TRIP

France : Provence

Hilltop Villages of Provence Cycling - Short Break

£1379


4.9 (7 reviews)

VIEW TRIP

Self-guided cycling

4 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
Navigation App

VIEW TRIP

Greece

Walking the Wonders of Crete

£1379

NEW FOR 2025

VIEW TRIP

Self-guided walking

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

VIEW TRIP

Spain : Extremadura

Cycling Central Spain in Style

£1389

NEW FOR 2025

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
Navigation App

VIEW TRIP

United Kingdom : Norfolk

Highlights of Norfolk Cycling

£1429


4.3 (10 reviews)

VIEW TRIP

Self-guided cycling

5 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

VIEW TRIP

Portugal : Mainland Portugal

Cycling in Portugal: From the Mountains to the Sea

£1429


4.5 (16 reviews)

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

Spain : The Canary Islands

Walking in Gran Canaria and La Palma

£1439

 
 

VIEW TRIP

Self-guided walking

7 nights,
twin centre

Level: 1 to 2+

Headwater
Navigation App

VIEW TRIP

Switzerland : Valais

Walk in the Home of the Matterhorn

£1469


5.0 (1 reviews)

VIEW TRIP

Self-guided walking

7 nights,
single centre

Level: 1 to 3

Headwater
Navigation App

VIEW TRIP

Spain : Galicia

Cycling the Camino de Santiago

£1479


4.5 (6 reviews)

VIEW TRIP

Self-guided pilgrimage

8 nights,
hotel-to-hotel

Level: 3
Stretching

Headwater
Navigation App

VIEW TRIP

Switzerland : Valais

Walking the Valais Matterhorn Region - Premium

£1479


5.0 (2 reviews)

VIEW TRIP

Self-guided walking

7 nights,
twin centre

Level: 2+ & 3

Headwater
Navigation App

VIEW TRIP

France : Mont Blanc

Walking Tour du Mont Blanc

£1499

 
 

VIEW TRIP

Self-guided walking

7 nights,
twin centre

Level: 3
Stretching

Headwater
Navigation App

VIEW TRIP

United Kingdom : The Channel Islands

Walking in Jersey, Guernsey and Sark Premium

£1509

 
 

VIEW TRIP

Self-guided walking

6 nights,
twin centre

Level: 1+
Leisurely plus

Headwater
Navigation App

VIEW TRIP

United Kingdom : Wales

Walking Offa's Dyke Path (North)

£1549

 
 

VIEW TRIP

Self-guided walking

9 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
Navigation App

VIEW TRIP

United Kingdom : The Cotswolds

Best of the Cotswolds Cycling

£1559


4.0 (1 reviews)

VIEW TRIP

Self-guided cycling

6 nights,
twin centre

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

Portugal : The Algarve

Walking the Algarve's South West

£1609


4.8 (32 reviews)

VIEW TRIP

Self-guided walking

10 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

VIEW TRIP

France : Mont Blanc

Walking Tour du Mont Blanc - Premium

£1669


4.8 (4 reviews)

VIEW TRIP

Self-guided walking

7 nights,
twin centre

Level: 3
Stretching

Headwater
Navigation App

VIEW TRIP

Sweden : sweden

Stockholm to Copenhagen Cycling

£1709


4.3 (3 reviews)

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

VIEW TRIP

Portugal : Mainland Portugal

Porto to Coimbra Cycling

£1729


4.8 (56 reviews)

VIEW TRIP

Self-guided cycling

9 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

VIEW TRIP

Slovenia

Secrets of Slovenia Cycling

£1759


4.9 (11 reviews)

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
Navigation App

VIEW TRIP

Portugal : The Azores

Island Hopping in the Azores

£1819


4.3 (3 reviews)

VIEW TRIP

Self-guided walking

14 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

Italy : Puglia

Highlights of Puglia Cycling

£1869


4.8 (11 reviews)

VIEW TRIP

Self-guided cycling

10 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

VIEW TRIP

France : Provence

Vineyards of Vaucluse Cycling

£2019


4.8 (18 reviews)

VIEW TRIP

Self-guided cycling

8 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

VIEW TRIP

Italy : Piedmont

Walking the Wine Villages of Piedmont

£2049


4.5 (4 reviews)

VIEW TRIP

Self-guided walking

8 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

United Kingdom : The Cotswolds

The Cotswold Way Walk

£2109


3.7 (3 reviews)

VIEW TRIP

Self-guided walking

9 nights,
hotel-to-hotel

Level: 2
Moderate

Printed route
directions

VIEW TRIP

Italy : Piedmont

Cycling the Wine Villages of Piedmont by e-bike

£2199


4.8 (5 reviews)

VIEW TRIP

Self-guided cycling

8 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
Navigation App

VIEW TRIP

Iceland

Walking Iceland's Diamond Circle

£2199

NEW FOR 2025

VIEW TRIP

Self-guided walking

7 nights,
hotel-to-hotel

Level: 1 to 3

Headwater
Navigation App

VIEW TRIP

United Kingdom : Wales

Walking Offa's Dyke Path (North to South)

£2419

 
 

VIEW TRIP

Self-guided walking

17 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
Navigation App

VIEW TRIP

Canada

Walking Canada’s Sunshine Coast

£2449


4.7 (3 reviews)

VIEW TRIP

Self-guided walking

8 nights,
hotel-to-hotel

Level: 1 to 3

Headwater
Navigation App

VIEW TRIP

USA : Maine

Cycling Maine's Coast & National Park

£3039

 
 

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
Navigation App

VIEW TRIP

Japan

Japan: Hiroshima & Island Hopping

£3399

NEW FOR 2025

VIEW TRIP

Multi-activity holiday

10 nights,
hotel-to-hotel

Level: 2
Moderate

Printed route
directions

VIEW TRIP
Tap here to filter results

Filter and sort

Holiday type
All

  • Self-guided walking
  • Self-guided cycling
  • Winter holidays
  • Canoeing
  • Multi activity
  • Pilgrimage
  • Private guided group
  • 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
  • Germany
  • Gozo
  • Greece
  • Holland
  • Iceland
  • Ireland
  • Japan
  • Kenya
  • Malta
  • Montenegro
  • Morocco
  • Nepal
  • Norway
  • Peru
  • Romania
  • 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

Activty level
All


  • Leisurely

  • Moderate

  • Demanding

  • Challenging

Accommodation type
All


  • Single centre

  • Twin centre  

  • Hotel-to-hotel

Best for
GPS navigation

  • 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.