Holidays with the Headwater Navigation App

Showing 172 out of 337 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

CA$1075

NEW FOR 2025

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Self-guided walking

4 nights,
single centre

Level: 1+
Leisurely plus

Headwater
Navigation App

VIEW TRIP

Malta

Highlights of Secrets of Malta Walking

CA$1130

 
 

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Self-guided walking

4 nights,
single centre

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

United Kingdom : The Channel Islands

Walking in Jersey Premium

CA$1400

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

CA$1400

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

CA$1550


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

CA$1685

 
 

VIEW TRIP

Self-guided walking

7 nights,
single centre

Level: 2 & 3

Headwater
Navigation App

VIEW TRIP

Spain : Andalucia

Walking in Sierra de Aracena

CA$1815


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

CA$1910


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

CA$1930


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

CA$1950


5.0 (1 reviews)

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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

CA$1970


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

CA$1985


5.0 (2 reviews)

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Self-guided walking

7 nights,
single centre

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

Spain : The Canary Islands

Contrasts of La Gomera

CA$2005


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

CA$2045


4.8 (11 reviews)

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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

CA$2065


4.4 (7 reviews)

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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

CA$2080


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

CA$2175

NEW FOR 2025

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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

CA$2215


4.6 (12 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

Albania

E-bike Across Southern Albania

CA$2270

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

CA$2350


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

CA$2350


4.8 (13 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

Greece

Cycling in the Peloponnese

CA$2555


4.8 (11 reviews)

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

Portugal : The Algarve

Walking Rota Vicentina North Fishermen's Trail

CA$2555

 
 

VIEW TRIP

Self-guided walking

8 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

Italy : Italian Lakes

Walking at Lakes Orta and Maggiore

CA$2825

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

CA$2840


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

CA$2900

 
 

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

CA$2975


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

CA$3070

 
 

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)

CA$3715

 
 

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

CA$3790

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

CA$5160

NEW FOR 2025

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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

CA$2100

NEW FOR 2025

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Self-guided walking

7 nights,
twin centre

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

Italy : The Bay of Naples

The Amalfi Coast Walk

CA$4020


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

CA$2785


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

CA$1625


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)

CA$2425


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

CA$1590


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

CA$1720


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

CA$1815


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

CA$1985


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

CA$2120


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

CA$2255


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

CA$2405


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

CA$2425


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

CA$2520


4.9 (27 reviews)

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Self-guided cycling

7 nights,
single centre

Level: 2+
Moderate plus

Headwater
Navigation App

VIEW TRIP

Portugal : Madeira

Marvels of Madeira Walk

CA$2520


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

CA$2635


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

CA$2635


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

CA$2710


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

CA$2825


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

CA$3015


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

CA$3015


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

CA$3490


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

CA$3790


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

CA$4075


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

CA$1760


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

CA$2195


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

CA$2235


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

CA$2255


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

CA$2255


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

CA$2290


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

CA$2445


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

CA$2635


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

CA$2670


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

CA$2765


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

CA$2825


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

CA$2840


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

CA$2860


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

CA$2955


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

CA$3015


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

CA$3205


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

CA$3525


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

CA$3830


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

CA$4570


4.8 (88 reviews)

VIEW TRIP

Self-guided cycling

8 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
Navigation App

VIEW TRIP

Spain : Andalucia

Hidden Valleys of Cordoba Walk

CA$1095


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

CA$1130


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

CA$1380


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

CA$1400


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

CA$1455


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

CA$1455


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

CA$1550


4.5 (6 reviews)

VIEW TRIP

Self-guided walking

7 nights,
hotel-to-hotel

Level: 2 & 2+

Headwater
Navigation App

VIEW TRIP

Portugal : Madeira

Walk the Garden Island of Madeira

CA$1570


4.7 (3 reviews)

VIEW TRIP

Self-guided walking

7 nights,
single centre

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

Spain : Asturias

Highlights of the Picos de Europa

CA$1570


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

CA$1570

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

CA$1605


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

CA$1625


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

CA$1645


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

CA$1700


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

CA$1720

 
 

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

CA$1740


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

CA$1760


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

CA$1780


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

CA$1795


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

CA$1795


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

CA$1815


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

CA$1835


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

CA$1910


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

CA$1970


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

CA$1970

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

CA$1985

 
 

VIEW TRIP

Self-guided walking

4 nights,
hotel-to-hotel

Level: 1
Leisurely

Headwater
Navigation App

VIEW TRIP

Sweden : sweden

Cycling from Stockholm

CA$315

 
 

VIEW TRIP

Self-guided cycling

5 nights,
single centre

Level: 1+
Leisurely plus

Headwater
Navigation App

VIEW TRIP

Spain : The Canary Islands

Highlights of El Hierro Walk

CA$2025


4.9 (10 reviews)

VIEW TRIP

Self-guided walking

7 nights,
hotel-to-hotel

Level: 2+ & 3

Headwater
Navigation App

VIEW TRIP

Spain : The Canary Islands

Walking in El Hierro

CA$2045


5.0 (1 reviews)

VIEW TRIP

Self-guided walking

7 nights,
single centre

Level: 1 to 2+

Headwater
Navigation App

VIEW TRIP

Austria : The Tyrol

Alpine Walks in the Stubai Valley

CA$2045


4.6 (11 reviews)

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Self-guided walking

7 nights,
single centre

Level: 2
Moderate

Headwater
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Austria : The Tyrol

Walking the Tyrolean Mountains

CA$2080


5.0 (1 reviews)

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Self-guided walking

6 nights,
single centre

Level: 2
Moderate

Headwater
Navigation App

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Andorra

Walk across Andorra

CA$2080


4.6 (5 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 4
Challenging

Headwater
Navigation App

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United Kingdom : Wales

Highlights of the Gower Peninsula Walk

CA$2120


5.0 (2 reviews)

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Self-guided walking

5 nights,
twin centre

Level: 1+
Leisurely plus

Headwater
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United Kingdom : Devon

Walking South Devon's Coastal Path

CA$2140


5.0 (1 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

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Italy : Campania

Coastal Cilento Walk

CA$2140


4.8 (5 reviews)

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Self-guided walking

8 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
Navigation App

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Italy : The Bay of Naples

Gems of the Amalfi Coast Walking

CA$2160


4.7 (3 reviews)

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Self-guided walking

7 nights,
twin centre

Level: 2
Moderate

Headwater
Navigation App

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France : Mont Blanc

Mont Blanc Walks – Short Break

CA$2195

 
 

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Self-guided walking

4 nights,
single centre

Level: 2+
Moderate plus

Headwater
Navigation App

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Switzerland : The Bernese Oberland

Walking in Kandersteg - Short Break

CA$2195


4.9 (12 reviews)

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Self-guided walking

5 nights,
single centre

Level: 2
Moderate

Headwater
Navigation App

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Switzerland : The Bernese Oberland

Walk the Crossroads of Five Passes

CA$2195


4.8 (5 reviews)

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Self-guided walking

7 nights,
single centre

Level: 1 to 3

Headwater
Navigation App

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Austria : Lake Constance

Highlights of Lake Constance by bike

CA$2215


4.9 (26 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1
Leisurely

Headwater
Navigation App

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Spain : Catalonia

Classic Catalan Cycling

CA$2215


4.8 (11 reviews)

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Self-guided cycling

8 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

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United Kingdom : The Channel Islands

Walking in Jersey, Guernsey and Sark

CA$2215


4.4 (14 reviews)

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Self-guided walking

6 nights,
twin centre

Level: 1+ & 2

Headwater
Navigation App

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United Kingdom : Wales

Walk the Welsh Highland Railway

CA$2255


3.7 (3 reviews)

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Self-guided walking

6 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

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Italy : Umbria

Walking on the Francigena Way

CA$2255


4.6 (11 reviews)

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Self-guided pilgrimage

9 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
Navigation App

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Bosnia

Walking the Olympic Mountains of Bosnia

CA$2270

NEW FOR 2025

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

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Spain : Galicia

Highlights of the Camino de Santiago Walk

CA$2310


4.9 (16 reviews)

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Self-guided pilgrimage

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

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Greece

Cycling the Coast of Eastern Crete

CA$2330


4.0 (2 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 3
Stretching

Headwater
Navigation App

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Spain : Valencia

Cycling Valencia and the Orange Blossom Coast

CA$2385


4.5 (8 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

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France : Burgundy

Walking in Burgundy’s Vineyards

CA$2385


4.7 (6 reviews)

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Self-guided walking

6 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

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France : Mont Blanc

Mont Blanc Walks – Short Break Premium

CA$2425

 
 

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Self-guided walking

4 nights,
single centre

Level: 2+
Moderate plus

Headwater
Navigation App

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Spain : Andalucia

E-biking in Andalucia: Sierra de Aracena

CA$2445

NEW FOR 2025

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

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Greece : Peloponnese

Walking the Historical Paths of Outer Mani

CA$2460

NEW FOR 2025

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

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United Kingdom : Wales

Walking Offa's Dyke Path (South)

CA$2480

 
 

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Self-guided walking

8 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
Navigation App

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Croatia

Hike, Bike & Paddle Croatia

CA$2500

NEW FOR 2025

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Multi-activity holiday

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

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Greece : Peloponnese

Peloponnese Coast and Mountain Walking

CA$2500

NEW FOR 2025

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

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France : Provence

Hilltop Villages of Provence Cycling

CA$2540


4.8 (16 reviews)

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Self-guided cycling

6 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
Navigation App

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Montenegro

Highlights of Southern Montenegro Walk

CA$2540


5.0 (1 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
Navigation App

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Greece

Walking on Kythnos Island - Premium

CA$2595


4.6 (7 reviews)

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Self-guided walking

6 nights,
twin centre

Level: 2+
Moderate plus

Headwater
Navigation App

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Portugal : Mainland Portugal

Walk the Highlights of Northern Portugal

CA$2615


4.5 (6 reviews)

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Self-guided walking

8 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
Navigation App

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Spain : Rioja

Vineyards of La Rioja Cycling

CA$2635


4.6 (7 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

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France : Alsace

Villages & Vineyards of Alsace

CA$2635


4.4 (7 reviews)

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Self-guided walking

6 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

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Sweden : sweden

Cycling Stockholm's Archipelago

CA$2650


5.0 (1 reviews)

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Self-guided cycling

6 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

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Portugal : The Algarve

Cycling the Algarve's Rota Vicentina

CA$2650


4.9 (8 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
Navigation App

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France : The Dordogne

Dordogne Activities

CA$2650


4.8 (31 reviews)

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Multi-activity holiday

8 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

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Spain : Catalonia

Contrasts of Catalunya Cycling - Short Break

CA$2710


4.6 (5 reviews)

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Self-guided cycling

4 nights,
hotel-to-hotel

Level: 1
Leisurely

Headwater
Navigation App

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Norway

Walking in Balestrand

CA$2745


4.7 (3 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 1 to 3

Headwater
Navigation App

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Italy : Tuscany

Cycling the hills of San Gimignano by E-bike

CA$2785

NEW FOR 2025

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Self-guided cycling

7 nights,
single centre

Level: 2+ & 3

Headwater
Navigation App

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Portugal : The Azores

Azores By E-bike

CA$2805


4.0 (4 reviews)

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Self-guided cycling

6 nights,
hotel-to-hotel

Level: 3
Stretching

Headwater
Navigation App

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France : Provence

Hilltop Villages of Provence Cycling - Short Break

CA$2825


4.9 (7 reviews)

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Self-guided cycling

4 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
Navigation App

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Spain : Extremadura

Cycling Central Spain in Style

CA$2840

NEW FOR 2025

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
Navigation App

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United Kingdom : Norfolk

Highlights of Norfolk Cycling

CA$2920


4.3 (10 reviews)

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Self-guided cycling

5 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

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Portugal : Mainland Portugal

Cycling in Portugal: From the Mountains to the Sea

CA$2920


4.5 (16 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

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Spain : The Canary Islands

Walking in Gran Canaria and La Palma

CA$2935

 
 

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Self-guided walking

7 nights,
twin centre

Level: 1 to 2+

Headwater
Navigation App

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Greece

Walking the Wonders of Crete

CA$2935

NEW FOR 2025

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

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Switzerland : Valais

Walk in the Home of the Matterhorn

CA$2995


5.0 (1 reviews)

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Self-guided walking

7 nights,
single centre

Level: 1 to 3

Headwater
Navigation App

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Spain : Galicia

Cycling the Camino de Santiago

CA$3015


4.5 (6 reviews)

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Self-guided cycling

8 nights,
hotel-to-hotel

Level: 3
Stretching

Headwater
Navigation App

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Switzerland : Valais

Walking the Valais Matterhorn Region - Premium

CA$3015


5.0 (2 reviews)

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Self-guided walking

7 nights,
twin centre

Level: 2+ & 3

Headwater
Navigation App

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France : Mont Blanc

Walking Tour du Mont Blanc

CA$3050

 
 

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Self-guided walking

7 nights,
twin centre

Level: 3
Stretching

Headwater
Navigation App

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United Kingdom : The Channel Islands

Walking in Jersey, Guernsey and Sark Premium

CA$3070

 
 

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Self-guided walking

6 nights,
twin centre

Level: 1+
Leisurely plus

Headwater
Navigation App

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United Kingdom : Wales

Walking Offa's Dyke Path (North)

CA$3145

 
 

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Self-guided walking

9 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
Navigation App

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United Kingdom : The Cotswolds

Best of the Cotswolds Cycling

CA$3165


4.0 (1 reviews)

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Self-guided cycling

6 nights,
twin centre

Level: 2
Moderate

Headwater
Navigation App

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Portugal : The Algarve

Walking the Algarve's South West

CA$3260


4.8 (32 reviews)

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Self-guided walking

10 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

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Italy : Italian Lakes

Cycling the Italian Lakes

CA$3335


4.0 (1 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

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France : Mont Blanc

Walking Tour du Mont Blanc - Premium

CA$3375


4.8 (4 reviews)

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Self-guided walking

7 nights,
twin centre

Level: 3
Stretching

Headwater
Navigation App

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Sweden : sweden

Stockholm to Copenhagen Cycling

CA$3450


4.3 (3 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

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Portugal : Mainland Portugal

Porto to Coimbra Cycling

CA$3490


4.8 (56 reviews)

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Self-guided cycling

9 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

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Slovenia

Secrets of Slovenia Cycling

CA$3545


4.9 (11 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
Navigation App

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Portugal : The Azores

Island Hopping in the Azores

CA$3660


4.3 (3 reviews)

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Self-guided walking

14 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

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Italy : Puglia

Highlights of Puglia Cycling

CA$3755


4.8 (11 reviews)

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Self-guided cycling

10 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

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France : Provence

Vineyards of Vaucluse Cycling

CA$4040


4.8 (18 reviews)

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Self-guided cycling

8 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

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Italy : Piedmont

Walking the Wine Villages of Piedmont

CA$4095


4.5 (4 reviews)

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Self-guided walking

8 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

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United Kingdom : The Cotswolds

The Cotswold Way Walk

CA$4210


3.7 (3 reviews)

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Self-guided walking

9 nights,
hotel-to-hotel

Level: 2
Moderate

Printed route
directions

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Italy : Piedmont

Cycling the Wine Villages of Piedmont by e-bike

CA$4380


4.8 (5 reviews)

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Self-guided cycling

8 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
Navigation App

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Iceland

Walking Iceland's Diamond Circle

CA$4380

NEW FOR 2025

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 1 to 3

Headwater
Navigation App

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United Kingdom : Wales

Walking Offa's Dyke Path (North to South)

CA$4800

 
 

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Self-guided walking

17 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
Navigation App

VIEW TRIP

Canada

Walking Canada’s Sunshine Coast

CA$4855


4.7 (3 reviews)

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Self-guided walking

8 nights,
hotel-to-hotel

Level: 1 to 3

Headwater
Navigation App

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USA : Maine

Cycling Maine's Coast & National Park

CA$5975

 
 

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
Navigation App

VIEW TRIP

Japan

Japan: Hiroshima & Island Hopping

CA$6660

NEW FOR 2025

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Multi-activity holiday

10 nights,
hotel-to-hotel

Level: 2
Moderate

Printed route
directions

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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.