Rethink Food

Showing 191 out of 333 trips

Delicious meals, fine wines and the warmest of welcomes: this is what defines the gastronomic experience of a Headwater guest.

Provenance is everything, with the high quality of meals divined from the very freshest local ingredients with passionate, creative chefs at the helm. Each regional delicacy you taste is created by highly skilled artisan - even Michelin starred - chefs. We've hunted out the best of the region, whether that be the hidden gem of a family-run vineyard, an included cheese tasting along the way, or your stay at a beautiful converted farmhouse where the freshest ingredients travel mere metres from field to plate. Our routes take you to gastronomic heaven and back, with flavours that reflect each region's identity, elevated by world-class chefs.

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United Kingdom : Devon

The English Riviera & Dart Valley Walk

CA$1455


5.0 (1 reviews)

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Self-guided walking

4 nights,
twin centre

Level: 2
Moderate

Printed route
directions

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United Kingdom : The Channel Islands

Walking in Guernsey and Sark

CA$1475

NEW FOR 2025

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Self-guided walking

3 nights,
single centre

Level: 1+ & 2

Headwater
Navigation App

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United Kingdom : The Channel Islands

Walking in Jersey Premium

CA$1590

NEW FOR 2025

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Self-guided walking

3 nights,
single centre

Level: 1+ & 2

Headwater
Navigation App

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Spain : Andalucia

Walking in Sierra de Aracena

CA$2005


4.8 (15 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 1
Leisurely

Headwater
Navigation App

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Spain : Asturias

Majestic Mountains of the Picos de Europa

CA$2080


4.7 (10 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 2 & 3

Navigation App

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Austria : The Tyrol

Walking the Kitzbuhel Alps Trail

CA$2120

NEW FOR 2025

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Self-guided walking

6 nights,
hotel-to-hotel

Level: 3
Stretching

Printed route
directions

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Denmark

Cycling from Copenhagen

CA$2140


5.0 (1 reviews)

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Self-guided cycling

4 nights,
single centre

Level: 1
Leisurely

Headwater
Navigation App

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United Kingdom : Scotland

Walking St Cuthbert's Way

CA$2140


4.5 (2 reviews)

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Self-guided walking

6 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Navigation App

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Spain : The Canary Islands

Contrasts of Lanzarote

CA$2175


5.0 (4 reviews)

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Self-guided walking

7 nights,
single centre

Level: 2
Moderate

Headwater
Navigation App

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Italy : Puglia

Cycling the Heel of Italy - Alberobello to Lecce

CA$2195


4.7 (44 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

Contrasts of La Gomera

CA$2195


4.2 (5 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

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United Kingdom : Scotland

Walking the Speyside Way

CA$2215


4.5 (2 reviews)

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Self-guided walking

6 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Navigation App

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Portugal : Madeira

Walking the Waterways and villages of Madeira

CA$2215


4.2 (6 reviews)

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Self-guided walking

7 nights,
single centre

Level: 2+
Moderate plus

Headwater
Navigation App

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Italy : Umbria

Undiscovered Villages of Umbria Walk

CA$2235


4.7 (15 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

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Spain : The Canary Islands

Walking on Gran Canaria

CA$2270


5.0 (7 reviews)

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Self-guided walking

7 nights,
twin centre

Level: 2
Moderate

Headwater
Navigation App

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Italy : The Dolomites

Cycling from the Dolomites to Venice

CA$2330


4.6 (8 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Navigation App

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Spain : The Canary Islands

Walking in Fuerteventura along the GR 131

CA$2365

NEW FOR 2025

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 2 & 2+

Headwater
Navigation App

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Italy : Puglia

Journey through Puglia to Matera

CA$2385


4.8 (13 reviews)

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Self-guided cultural tour

7 nights,
hotel-to-hotel

Headwater
Navigation App

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United Kingdom : Scotland

Walking the Rob Roy Way

CA$2445

 
 

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Self-guided walking

8 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Navigation App

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Albania

E-bike Across Southern Albania

CA$2460

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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France : The Pyrenees

Basque Country : From the Mountains to the Ocean

CA$2480


4.5 (2 reviews)

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Self-guided walking

6 nights,
hotel-to-hotel

Level: 2
Moderate

Printed route
directions

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United Kingdom : Scotland

Walking the West Highland Way

CA$2480


4.3 (4 reviews)

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Self-guided walking

8 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Navigation App

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Italy : Umbria

The Wine Trails of Umbria Cycling

CA$2540


5.0 (2 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

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Croatia

Dalmatian Coast Island Hopping

CA$2540


4.8 (20 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

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France : Brittany

St Malo to Mont St Michel Cycling

CA$2670

 
 

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Self-guided cycling

6 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Navigation App

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Spain : The Canary Islands

Walking across La Gomera

CA$2745

NEW FOR 2025

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 2 & 3

Headwater
Navigation App

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France : Normandy

Normandy Walk from Deauville to Bayeux - Deluxe

CA$2805


5.0 (2 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 1
Leisurely

Printed route
directions

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Portugal : The Algarve

Walking Rota Vicentina North Fishermen's Trail

CA$2840


4.5 (2 reviews)

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Self-guided walking

8 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

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Greece : Crete

Cycling in the Peloponnese

CA$2880


4.8 (12 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

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Italy : Trentino

Brenner Pass to Venice Cycling

CA$2995


5.0 (2 reviews)

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Self-guided cycling

9 nights,
hotel-to-hotel

Level: 2
Moderate

Navigation App

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Belgium

Cycling from Bruges to Amsterdam

CA$3090


4.0 (1 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Navigation App

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Portugal : Mainland Portugal

Cycling in the Douro Valley

CA$3090

 
 

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 3
Stretching

Headwater
Navigation App

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United Kingdom : The Channel Islands

Cycling in Jersey, Guernsey and Sark

CA$3125


4.0 (1 reviews)

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Self-guided cycling

6 nights,
twin centre

Level: 1+
Leisurely plus

Headwater
Navigation App

VIEW TRIP

Italy : Puglia

Cycling the Heel of Italy - Matera to Lecce

CA$3300


4.7 (14 reviews)

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Self-guided cycling

11 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

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France : Atlantic Coast

Cycling along the Atlantic Coast

CA$3695

NEW FOR 2025

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Navigation App

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Spain : The Canary Islands

Contrasts of Tenerife Walk (with transfers)

CA$3905

 
 

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Self-guided walking

7 nights,
twin centre

Level: 1+ to 2+

Headwater
Navigation App

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Portugal : Mainland Portugal

Coimbra to Lisbon Cycling

CA$3980

NEW FOR 2025

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Self-guided cycling

11 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

VIEW TRIP

Norway

Cycling Norway's Fjords: Hardangerfjord from Bergen

CA$5180

NEW FOR 2025

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Self-guided cycling

5 nights,
hotel-to-hotel

Level: 2 & 3

Printed route
directions

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Norway

Cycling the Norwegian Archipelago South of Bergen

CA$5825

NEW FOR 2025

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Self-guided cycling

6 nights,
hotel-to-hotel

Level: 2 & 3

Printed route
directions

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Norway

Walking Norway's Fjords: Hardangerfjord from Bergen

CA$6395

NEW FOR 2025

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Self-guided walking

8 nights,
hotel-to-hotel

Level: 2 & 3

Printed route
directions

VIEW TRIP

Norway

Cycling in the Lofoten Islands

CA$7495


5.0 (2 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Navigation App

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France : The Loire

Chateaux Of The Loire Walk

CA$2785


4.4 (7 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 1
Leisurely

Navigation App

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France : Corsica

North Corsican Wonders Between Coast and Mountains

CA$2650


4.0 (3 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 2 & 2+

Printed route
directions

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Spain : The Canary Islands

Contrasts of Tenerife Walk (with car hire)

CA$2615


4.7 (11 reviews)

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Self-guided walking

7 nights,
twin centre

Level: 1+ to 2+

Headwater
Navigation App

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Italy : The Bay of Naples

Paths of the Amalfi Coast

CA$1780


4.6 (28 reviews)

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Self-guided walking

7 nights,
single centre

Level: 2
Moderate

Headwater
Navigation App

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Italy : The Bay of Naples

Walking Amalfi's Path of the Gods

CA$1910


5.0 (2 reviews)

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Self-guided walking

7 nights,
single centre

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

Italy : Veneto

Heart of Veneto Cycling

CA$2235


4.8 (73 reviews)

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Self-guided cycling

7 nights,
single centre

Level: 1
Leisurely

Headwater
Navigation App

VIEW TRIP

Italy : Veneto

Walking in the Venetian Hills

CA$2270


4.7 (90 reviews)

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Self-guided walking

8 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

VIEW TRIP

Italy : Puglia

Self Guided Walking in Puglia: From Lecce to Matera

CA$2425


4.7 (64 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 1
Leisurely

Headwater
Navigation App

VIEW TRIP

Italy : Sicily

Secrets of Sicily Cycling

CA$2595


4.6 (24 reviews)

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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$2615


4.9 (31 reviews)

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Self-guided walking

7 nights,
single centre

Level: 2
Moderate

Headwater
Navigation App

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Italy : Tuscany

A Taste of Tuscany Cycling

CA$2710


4.9 (28 reviews)

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Self-guided cycling

7 nights,
single centre

Level: 2+
Moderate plus

Headwater
Navigation App

VIEW TRIP

Italy : The Dolomites

Walks in The Italian Dolomites

CA$2805


4.9 (127 reviews)

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Self-guided walking

7 nights,
single centre

Level: 2+
Moderate plus

Headwater
Navigation App

VIEW TRIP

Portugal : The Algarve

Cycling in The Real Algarve

CA$2900


4.7 (66 reviews)

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Self-guided cycling

6 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

Italy : The Dolomites

Walking the Dolomites of Alta Badia

CA$3205


4.8 (23 reviews)

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Self-guided walking

7 nights,
single centre

Level: 2+
Moderate plus

Headwater
Navigation App

VIEW TRIP

Italy : Sicily

Cycling through Baroque Sicily

CA$3220


4.5 (22 reviews)

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Self-guided cycling

8 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

Slovenia

Julian Alps to the Adriatic Cycling

CA$4440


4.8 (123 reviews)

VIEW TRIP

Self-guided cycling

10 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

VIEW TRIP

Spain : Catalonia

Catalan Classic Walk

CA$2080


4.7 (79 reviews)

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Self-guided walking

6 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

VIEW TRIP

United Kingdom : Cornwall

Walking Cornwall's North coast Padstow to Perranporth

CA$2140

 
 

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Self-guided walking

5 nights,
hotel-to-hotel

Level: 2
Moderate

Printed route
directions

VIEW TRIP

Switzerland : The Bernese Oberland

Classic Swiss Alps Walk

CA$2350


4.8 (141 reviews)

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Self-guided walking

7 nights,
single centre

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

France : The Dordogne

Dordogne Valleys & Villages Cycling

CA$2425


4.7 (45 reviews)

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Self-guided cycling

8 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

Portugal : The Algarve

Walk the Algarve's Wild West

CA$2445


4.8 (90 reviews)

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Self-guided walking

6 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

VIEW TRIP

France : The Dordogne

Dordogne River Walk

CA$2480


4.7 (31 reviews)

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Self-guided walking

8 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

Spain : Catalonia

Contrasts of Catalunya Cycling

CA$2615


4.7 (56 reviews)

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Self-guided cycling

6 nights,
hotel-to-hotel

Level: 1
Leisurely

Headwater
Navigation App

VIEW TRIP

Spain : Andalucia

White Villages of Andalucia Walk

CA$2670


4.9 (138 reviews)

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Guided group walking

7 nights,
single centre

Level: 1+
Leisurely plus

Printed route
directions

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Spain : Andalucia

Cycling in Andalucia: Seville to Cadiz

CA$2955


4.4 (17 reviews)

VIEW TRIP

Self-guided cycling

6 nights,
hotel-to-hotel

Level: 3
Stretching

Headwater
Navigation App

VIEW TRIP

Italy : Puglia

Contrasts of Puglia Cycling

CA$2995


4.6 (125 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

VIEW TRIP

Austria : Lake Constance

Lake Constance Cycling

CA$3030


4.7 (91 reviews)

VIEW TRIP

Self-guided cycling

10 nights,
hotel-to-hotel

Level: 1
Leisurely

Headwater
Navigation App

VIEW TRIP

Portugal : Mainland Portugal

Porto Coastal Cycling

CA$3145


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$3205


4.7 (86 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$3525


4.8 (14 reviews)

VIEW TRIP

Self-guided walking

8 nights,
hotel-to-hotel

Level: 1
Leisurely

Printed route
directions

VIEW TRIP

Italy : Piedmont

Gastronomic Barolo Walk

CA$3640


4.9 (95 reviews)

VIEW TRIP

Self-guided walking

8 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

Norway : Gudbrandsdalen

Cross-country skiing at Venabu

CA$3850


4.8 (293 reviews)

VIEW TRIP

Winter snow holiday

7 nights,
single centre



VIEW TRIP

Italy : Piedmont

Gastronomic Barolo Cycling by e-bike

CA$4075


4.8 (88 reviews)

VIEW TRIP

Self-guided cycling

8 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
Navigation App

VIEW TRIP

Spain : Catalonia

Catalan Classic Walk - Short Break

CA$1645


4.7 (7 reviews)

VIEW TRIP

Self-guided walking

4 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

VIEW TRIP

Cyprus

Walking the Akamas Peninsula

CA$1645


4.5 (11 reviews)

VIEW TRIP

Self-guided walking

7 nights,
twin centre

Level: 1 & 2

Headwater
Navigation App

VIEW TRIP

Italy : Veneto

Walking in the Prosecco Hills

CA$1685

NEW FOR 2025

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Self-guided walking

5 nights,
hotel-to-hotel

Level: 1+ & 2

Navigation App

VIEW TRIP

Italy : Tuscany

Treasures of Tuscany Walk: San Gimignano to Volterra

CA$1760

NEW FOR 2025

VIEW TRIP

Self-guided walking

7 nights,
twin centre

Level: 2+
Moderate plus

Headwater
Navigation App

VIEW TRIP

Holland

Cycling from Amsterdam

CA$1795

NEW FOR 2025

VIEW TRIP

Self-guided cycling

3 nights,
single centre

Level: 1+
Leisurely plus

Navigation App

VIEW TRIP

France : Burgundy

Cycling in Beaune Vineyards

CA$1795


5.0 (1 reviews)

VIEW TRIP

Self-guided cycling

4 nights,
single centre

Level: 1+
Leisurely plus

Printed route
directions

VIEW TRIP

Greece

Walking on Kythnos Island

CA$1835


5.0 (2 reviews)

VIEW TRIP

Self-guided walking

6 nights,
twin centre

Level: 2+
Moderate plus

Headwater
Navigation App

VIEW TRIP

France : Champagne

Cycling the Vineyards of Champagne

CA$1875

 
 

VIEW TRIP

Self-guided cycling

3 nights,
single centre

Level: 2
Moderate

Navigation App

VIEW TRIP

Spain : Catalonia

Contrasts of Catalunya Cycling - Short Break

CA$1910


4.7 (6 reviews)

VIEW TRIP

Self-guided cycling

4 nights,
hotel-to-hotel

Level: 1
Leisurely

Headwater
Navigation App

VIEW TRIP

France : The Loire

Chateaux Of The Loire Walk - Short Break

CA$1950

 
 

VIEW TRIP

Self-guided walking

4 nights,
hotel-to-hotel

Level: 1
Leisurely

Navigation App

VIEW TRIP

France : Burgundy

Tour de France - Burgundy

CA$1970

NEW FOR 2025

VIEW TRIP

Self-guided cycling

3 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Navigation App

VIEW TRIP

Switzerland : The Bernese Oberland

Cross country skiing in Kandersteg - Short Break

CA$1970


4.8 (4 reviews)

VIEW TRIP

Winter snow holiday

5 nights,
single centre



VIEW TRIP

Switzerland : The Bernese Oberland

Cross country skiing in Kandersteg

CA$1970


4.7 (6 reviews)

VIEW TRIP

Winter snow holiday

7 nights,
single centre



VIEW TRIP

France : Alsace

Villages & Vineyards of Alsace- Short Break

CA$1985


5.0 (2 reviews)

VIEW TRIP

Self-guided walking

4 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

Italy : Puglia

Undiscovered Puglia Walk - Discovering the South-East Coast

CA$1985


4.8 (13 reviews)

VIEW TRIP

Self-guided walking

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

VIEW TRIP

France : Provence

Tour de France - Provence

CA$2005

NEW FOR 2025

VIEW TRIP

Self-guided cycling

3 nights,
hotel-to-hotel

Level: 3
Stretching

Navigation App

VIEW TRIP

Italy : The Dolomites

Cross country skiing in the Dolomites

CA$2005

NEW FOR 2025

VIEW TRIP

Winter snow holiday

7 nights,
single centre



VIEW TRIP

Austria : The Danube

Walking the Wachau Heritage Trail

CA$2065


5.0 (2 reviews)

VIEW TRIP

Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Navigation App

VIEW TRIP

Italy : Istria

Walking the Highlights of Istria: Italy, Slovenia & Croatia

CA$2100

NEW FOR 2025

VIEW TRIP

Self-guided walking

6 nights,
hotel-to-hotel

Level: 2
Moderate

Navigation App

VIEW TRIP

France : Burgundy

Classic Burgundy Cycling

CA$2120


4.0 (1 reviews)

VIEW TRIP

Self-guided cycling

4 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Printed route
directions

VIEW TRIP

France : Normandy

Normandy Walk from Deauville to Bayeux

CA$2140


4.8 (5 reviews)

VIEW TRIP

Self-guided walking

7 nights,
hotel-to-hotel

Level: 1
Leisurely

Printed route
directions

VIEW TRIP

Italy : Italian Lakes

Cycling Lake Garda with e-bike

CA$2160


4.5 (2 reviews)

VIEW TRIP

Self-guided cycling

6 nights,
single centre

Level: 2+
Moderate plus

Headwater
Navigation App

VIEW TRIP

France : Burgundy

Walking in Burgundy's Vineyards - Short Break

CA$2175

 
 

VIEW TRIP

Self-guided walking

4 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

VIEW TRIP

France : The Loire

Multi Activity in the Loire

CA$2215


5.0 (1 reviews)

VIEW TRIP

Multi-activity holiday

5 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Navigation App

VIEW TRIP

France : The Loire

Cycling The Chateaux Of The Loire - Short Break

CA$2235


4.7 (7 reviews)

VIEW TRIP

Self-guided cycling

5 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Navigation App

VIEW TRIP

France : The Loire

Cycling The UNESCO Loire Valley

CA$2235


5.0 (3 reviews)

VIEW TRIP

Self-guided cycling

5 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Navigation App

VIEW TRIP

Sweden : sweden

Cycling from Stockholm

CA$2235

 
 

VIEW TRIP

Self-guided cycling

5 nights,
single centre

Level: 1+
Leisurely plus

Headwater
Navigation App

VIEW TRIP

Greece

Walking on Kythnos Island - Premium

CA$2235


4.6 (7 reviews)

VIEW TRIP

Self-guided walking

6 nights,
twin centre

Level: 2+
Moderate plus

Headwater
Navigation App

VIEW TRIP

France : The Pyrenees

Mediterranean Pyrenees Coastal Walk from Collioure to Cadaques

CA$2255


5.0 (3 reviews)

VIEW TRIP

Self-guided walking

6 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

Italy : Sardinia

Walking Sardinia's Green Coast

CA$2255

NEW FOR 2025

VIEW TRIP

Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

Italy : Veneto

Adriatic Coast - Venice to Porec Ride

CA$2290

NEW FOR 2025

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Navigation App

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France : Alsace

Cycling the Wine Route of Alsace

CA$2350


4.8 (9 reviews)

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Self-guided cycling

5 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Navigation App

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Italy : Campania

Coastal Cilento Walk

CA$2350


4.9 (8 reviews)

VIEW TRIP

Self-guided walking

8 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
Navigation App

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France : Champagne

Cycle The Wine Route of Champagne

CA$2385

 
 

VIEW TRIP

Self-guided cycling

5 nights,
twin centre

Level: 2+ & 3

Navigation App

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Austria : Carinthia

Cycling the Lakes and Rivers of the Salzkammergut

CA$2405

 
 

VIEW TRIP

Self-guided cycling

6 nights,
single centre

Level: 2
Moderate

Navigation App

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Italy : The Bay of Naples

Gems of the Amalfi Coast Walking

CA$2460


4.8 (4 reviews)

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Self-guided walking

7 nights,
twin centre

Level: 2
Moderate

Headwater
Navigation App

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Bosnia

Walking the Olympic Mountains of Bosnia

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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France : Normandy

D-Day Beaches Of Normandy Cycling

CA$2480


4.6 (7 reviews)

VIEW TRIP

Self-guided cycling

5 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Printed route
directions

VIEW TRIP

Portugal : Mainland Portugal

Tour the Treasures of Portugal

CA$2480


4.8 (4 reviews)

VIEW TRIP

Self-guided cultural tour

7 nights,
twin centre



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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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Italy : Trentino

Wine & Walk in Chianti

CA$2500


4.0 (2 reviews)

VIEW TRIP

Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Printed route
directions

VIEW TRIP

Greece : Crete

Cycling the Coast of Eastern Crete

CA$2520


4.4 (5 reviews)

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 3
Stretching

Headwater
Navigation App

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United Kingdom : The Channel Islands

Walking in Jersey, Guernsey and Sark

CA$2520


4.4 (15 reviews)

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Self-guided walking

6 nights,
twin centre

Level: 1+ & 2

Headwater
Navigation App

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Italy : Umbria

Walking on the Francigena Way

CA$2520


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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France : Burgundy

Cycling The Grand Crus of Burgundy

CA$2575


5.0 (1 reviews)

VIEW TRIP

Self-guided cycling

6 nights,
twin centre

Level: 1+
Leisurely plus

Printed route
directions

VIEW TRIP

France : The Loire

Tour de France - Loire

CA$2635

NEW FOR 2025

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Self-guided cycling

5 nights,
hotel-to-hotel

Level: 3
Stretching

Navigation App

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France : Burgundy

Walking in Burgundy's Vineyards

CA$2635


4.8 (8 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 : Bordeaux

Cycling The Grand Crus of Bordeaux

CA$2650


4.5 (4 reviews)

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Self-guided cycling

5 nights,
hotel-to-hotel

Level: 2
Moderate

Navigation App

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France : The Dordogne

Canoeing on the Dordogne

CA$2670


4.9 (55 reviews)

VIEW TRIP

8 nights,
hotel-to-hotel

Printed route
directions



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France : The Loire

Cycling The UNESCO Loire Valley - Deluxe

CA$2670


4.3 (3 reviews)

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Self-guided cycling

5 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Navigation App

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France : Canal du Midi

Canal du midi Cycling : from Toulouse to Sete

CA$2710


4.8 (5 reviews)

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Self-guided cycling

6 nights,
hotel-to-hotel

Level: 2
Moderate

Navigation App

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France : The Loire

Canoeing on the Loire

CA$2730

 
 

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5 nights,
hotel-to-hotel

Navigation App



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France : Burgundy

Cycling the Vineyards From Beaune to Macon

CA$2730


4.8 (6 reviews)

VIEW TRIP

Self-guided cycling

6 nights,
hotel-to-hotel

Level: 1
Leisurely

Printed route
directions

VIEW TRIP

Ireland : County Wicklow

Unspoilt Ring of Kerry Cycling

CA$2730


4.4 (5 reviews)

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

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France : The Loire

Cycling The Chateaux Of The Loire - Upgraded Short

CA$2745


4.8 (4 reviews)

VIEW TRIP

Self-guided cycling

5 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Navigation App

VIEW TRIP

Belgium

Cycling from Brussels to Bruges

CA$2765


4.0 (2 reviews)

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Navigation App

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Germany : The Moselle

Meandering the Moselle Cycle Path

CA$2765

NEW FOR 2025

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1
Leisurely

Navigation App

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Spain : Andalucia

Three Cities of Andalucia

CA$2785


4.8 (6 reviews)

VIEW TRIP

Self-guided cultural tour

7 nights,
hotel-to-hotel



VIEW TRIP

France : The Loire

Cycling The Chateaux Of The Loire

CA$2805


4.5 (10 reviews)

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Navigation App

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Portugal : Mainland Portugal

Walk the Highlights of Northern Portugal

CA$2805


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$2825


4.6 (7 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

France : Alsace

Villages & Vineyards of Alsace

CA$2825


4.4 (7 reviews)

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Self-guided walking

6 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

France : The French Riviera

The French Riviera Golden Islands

CA$2825

NEW FOR 2025

VIEW TRIP

Self-guided walking

7 nights,
twin centre

Level: 1+
Leisurely plus

Printed route
directions

VIEW TRIP

France : Canal du Midi

Tour de France - Canal du Midi

CA$2840

NEW FOR 2025

VIEW TRIP

Self-guided cycling

4 nights,
hotel-to-hotel

Level: 3
Stretching

Navigation App

VIEW TRIP

France : The Dordogne

Dordogne Activities

CA$2840


4.8 (32 reviews)

VIEW TRIP

Multi-activity holiday

8 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

Sweden : sweden

Cycling Stockholm's Archipelago

CA$2860


5.0 (1 reviews)

VIEW TRIP

Self-guided cycling

6 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

VIEW TRIP

Spain : Balearic Islands

Walking Mallorca trails and traditional Fincas

CA$2880

NEW FOR 2025

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Navigation App

VIEW TRIP

France : Alsace

Cycling the Scenic Rhine: Strasbourg to Mainz

CA$2900

NEW FOR 2025

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Navigation App

VIEW TRIP

Portugal : The Algarve

Cycling the Algarve's Rota Vicentina

CA$2975


4.9 (9 reviews)

VIEW TRIP

Self-guided cycling

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

CA$2975

NEW FOR 2025

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Self-guided cycling

7 nights,
single centre

Level: 2+ & 3

Headwater
Navigation App

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France : The Pyrenees

Walking the Best of the High Pyrenees

CA$2995


4.7 (3 reviews)

VIEW TRIP

Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Printed route
directions

VIEW TRIP

Croatia

Hike, Bike & Paddle Croatia

CA$3015

NEW FOR 2025

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Multi-activity holiday

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

VIEW TRIP

Spain : Extremadura

Cycling Central Spain in Style

CA$3030

NEW FOR 2025

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
Navigation App

VIEW TRIP

France : Atlantic Coast

Tour de France - Atlantic Coast

CA$3050

NEW FOR 2025

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Self-guided cycling

5 nights,
hotel-to-hotel

Level: 2 & 2+

Navigation App

VIEW TRIP

Italy : Piedmont

Walking the Wine Villages of Piedmont

CA$3050


4.5 (4 reviews)

VIEW TRIP

Self-guided walking

8 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

Holland

Cycling from Amsterdam to Brussels

CA$3090


5.0 (3 reviews)

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Navigation App

VIEW TRIP

Italy : Sardinia

Undiscovered Sardinia Cycling

CA$3145


4.7 (19 reviews)

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Navigation App

VIEW TRIP

United Kingdom : The Channel Islands

Walking in Jersey, Guernsey and Sark Premium

CA$3185


5.0 (2 reviews)

VIEW TRIP

Self-guided walking

6 nights,
twin centre

Level: 1+
Leisurely plus

Headwater
Navigation App

VIEW TRIP

Italy : Emilia Romagna

Emilia Romagna: Bologna to Parma Cycling

CA$3205


4.7 (3 reviews)

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Navigation App

VIEW TRIP

Italy : Sicily

Sicily: Vino & Volcanoes

CA$3260


5.0 (2 reviews)

VIEW TRIP

Self-guided cultural tour

7 nights,
hotel-to-hotel

Headwater
Navigation App

VIEW TRIP

Greece : Crete

Walking the Wonders of Crete

CA$3260

NEW FOR 2025

VIEW TRIP

Self-guided walking

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

VIEW TRIP

France : Normandy

Paris to the Sea Along the Seine River

CA$3430

NEW FOR 2025

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Printed route
directions

VIEW TRIP

France : The Loire

Cycling The Chateaux Of The Loire - Upgraded

CA$3470


4.7 (7 reviews)

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Navigation App

VIEW TRIP

Italy : Piedmont

Cycling the Wine Villages of Piedmont by e-bike

CA$3490


4.8 (5 reviews)

VIEW TRIP

Self-guided cycling

8 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
Navigation App

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France : Provence

Provence Velo Vin Voyage

CA$3490


4.0 (1 reviews)

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Self-guided cultural tour

7 nights,
hotel-to-hotel



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Portugal : The Algarve

Walking the Algarve's South West

CA$3600


4.9 (34 reviews)

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Self-guided walking

10 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

VIEW TRIP

Sweden : sweden

Stockholm to Copenhagen Cycling

CA$3640


4.3 (4 reviews)

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

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France : Corsica

Corsica with Ebike

CA$3660


4.7 (3 reviews)

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2 & 2+

Printed route
directions

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Portugal : Mainland Portugal

Porto to Coimbra Cycling

CA$3680


4.8 (56 reviews)

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Self-guided cycling

9 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

VIEW TRIP

Denmark

Nordic Cities by Rail

CA$3680

NEW FOR 2025

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Self-guided cultural tour

9 nights,
hotel-to-hotel



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Slovenia

Secrets of Slovenia Cycling

CA$3715


4.9 (13 reviews)

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
Navigation App

VIEW TRIP

Italy : Italian Lakes

Cycling the Italian Lakes

CA$3735


4.8 (5 reviews)

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

Italy

Highlights of Puglia Cycling

CA$4115


4.8 (13 reviews)

VIEW TRIP

Self-guided cycling

10 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

VIEW TRIP

Norway : Gudbrandsdalen

Guided Walking in Venabu

CA$4610


4.8 (15 reviews)

VIEW TRIP

Guided group walking

7 nights,
single centre

Level: 2+
Moderate plus

VIEW TRIP

USA : Maine

Cycling Maine's Coast & National Park

CA$6280

 
 

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
Navigation App

VIEW TRIP

China

Walking the Charms of China - With Private Guide

CA$6435

 
 

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Private guided walking

10 nights,
hotel-to-hotel

Level: 2+
Moderate plus

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Japan

Shikoku Pilgrimage Trail

CA$6530


5.0 (1 reviews)

VIEW TRIP

Self-guided pilgrimage

10 nights,
hotel-to-hotel

Level: 3
Stretching

Printed route
directions

VIEW TRIP

Japan

Walk the Kumano Kodo

CA$6585


5.0 (4 reviews)

VIEW TRIP

Self-guided walking

10 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Printed route
directions

VIEW TRIP

Japan

Walk the Nakasendo Trail

CA$6660

 
 

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Self-guided walking

10 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Printed route
directions

VIEW TRIP

Japan

Japan: Hiroshima & Island Hopping

CA$6850

NEW FOR 2025

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Multi-activity holiday

10 nights,
hotel-to-hotel

Level: 2
Moderate

Printed route
directions

VIEW TRIP

Morocco

Atlas Panorama

CA$1235

 
 

VIEW TRIP

Guided group walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Printed route
directions

VIEW TRIP

Cyprus

Walking in North Cyprus

CA$1805


4.0 (1 reviews)

VIEW TRIP

Guided group walking

7 nights,
single centre

Printed route
directions

Operated by
Exodus Travels

VIEW TRIP

Greece

Mountains & Villages of Evia

CA$2090


4.8 (4 reviews)

VIEW TRIP

Guided group walking

7 nights,
single centre

Level: 2+
Moderate plus

Printed route
directions

VIEW TRIP

Spain : Mallorca

Walking in Mallorca

CA$2660


5.0 (6 reviews)

VIEW TRIP

Guided group walking

7 nights,
twin centre

Level: 2
Moderate

Printed route
directions

VIEW TRIP

Greece

Walking on the Greek Islands

CA$2755

 
 

VIEW TRIP

Guided group walking

7 nights,
hotel-to-hotel

Level: 1
Leisurely

Printed route
directions

VIEW TRIP

Italy : Puglia

Walking in Puglia & Matera

CA$2850


4.3 (12 reviews)

VIEW TRIP

Guided group walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Printed route
directions

VIEW TRIP

Italy : Sardinia

Walking in Sardinia

CA$2850


5.0 (1 reviews)

VIEW TRIP

Guided group walking

7 nights,
single centre

Level: 3
Stretching

Printed route
directions

VIEW TRIP

Italy : The Dolomites

Snowshoeing in the Dolomites - Premium Adventure

CA$3230

 
 

VIEW TRIP

Winter snow holiday

7 nights,
single centre

Printed route
directions

Operated by
Exodus Travels

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Italy : The Dolomites

Classic Dolomites - Premium

CA$3990


5.0 (1 reviews)

VIEW TRIP

Guided group walking

7 nights,
single centre

Level: 3
Stretching

Printed route
directions

VIEW TRIP

Portugal : Mainland Portugal

Portugal: Walking & Wine - Premium Adventure

CA$4560


4.5 (2 reviews)

VIEW TRIP

Guided group walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Printed route
directions

VIEW TRIP

South Africa

Cycling the Cape & Winelands

CA$5130

 
 

VIEW TRIP

Guided group cycling

11 nights,
hotel-to-hotel

Level: 3
Stretching

Printed route
directions

VIEW TRIP

Costa Rica

Discover Costa Rica

CA$5795

 
 

VIEW TRIP

Guided group walking

14 nights,
hotel-to-hotel

Level: 1
Leisurely

Printed route
directions

VIEW TRIP

Costa Rica

Costa Rica's Coastal Secrets

CA$7030

 
 

VIEW TRIP

Guided group walking

14 nights,
hotel-to-hotel

Level: 2
Moderate

Printed route
directions

VIEW TRIP

Thailand

Cycle Indochina & Angkor - Premium Adventure

CA$7885

 
 

VIEW TRIP

Guided group cycling

13 nights,
hotel-to-hotel

Level: 3
Stretching

Printed route
directions

VIEW TRIP

Peru

Peru Explorer

CA$8930

 
 

VIEW TRIP

Guided group walking

19 nights,
hotel-to-hotel

Level: 2
Moderate

Printed route
directions

VIEW TRIP

Japan

Japan's Kumano Kodo

CA$10165

 
 

VIEW TRIP

Guided group walking

13 nights,
hotel-to-hotel

Level: 3
Stretching

Printed route
directions

VIEW TRIP

Kenya

Kenya Photographic Safari with Paul Goldstein - Premium Adventure

CA$13680

 
 

VIEW TRIP

Guided group walking

6 nights,
single centre

Level: 3
Stretching

Printed route
directions

VIEW TRIP
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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.