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

$1190


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

$1205

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

$1295

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

$1625


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

$1685


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

$1715

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

$1730


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

$1730


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

$1760


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

$1775


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

$1775


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

$1790


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

$1790


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

$1805


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

$1835


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

$1880


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

$1910

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

$1925


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

$1970

 
 

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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

$1985

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

$2000


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

$2000


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

$2045


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

$2045


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

$2150

 
 

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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

$2210

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

$2255


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

$2285


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

$2315


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

$2405


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

$2480


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

$2480

 
 

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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

$2510


4.0 (1 reviews)

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Self-guided cycling

6 nights,
twin centre

Level: 1+
Leisurely plus

Headwater
Navigation App

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Italy : Puglia

Cycling the Heel of Italy - Matera to Lecce

$2645


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

$2960

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)

$3125

 
 

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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

$3185

NEW FOR 2025

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Self-guided cycling

11 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

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Norway

Cycling Norway's Fjords: Hardangerfjord from Bergen

$4130

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

$4640

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

$5090

NEW FOR 2025

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Self-guided walking

8 nights,
hotel-to-hotel

Level: 2 & 3

Printed route
directions

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Norway

Cycling in the Lofoten Islands

$5960


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

$2240


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

$2135


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)

$2105


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

$1445


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

$1550


5.0 (2 reviews)

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Self-guided walking

7 nights,
single centre

Level: 2
Moderate

Headwater
Navigation App

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Italy : Veneto

Heart of Veneto Cycling

$1805


4.8 (73 reviews)

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Self-guided cycling

7 nights,
single centre

Level: 1
Leisurely

Headwater
Navigation App

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Italy : Veneto

Walking in the Venetian Hills

$1835


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

$1955


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

$2090


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

$2105


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

$2180


4.9 (28 reviews)

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Self-guided cycling

7 nights,
single centre

Level: 2+
Moderate plus

Headwater
Navigation App

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Italy : The Dolomites

Walks in The Italian Dolomites

$2255


4.9 (127 reviews)

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Self-guided walking

7 nights,
single centre

Level: 2+
Moderate plus

Headwater
Navigation App

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Portugal : The Algarve

Cycling in The Real Algarve

$2330


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

$2570


4.8 (23 reviews)

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Self-guided walking

7 nights,
single centre

Level: 2+
Moderate plus

Headwater
Navigation App

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Italy : Sicily

Cycling through Baroque Sicily

$2585


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

$3545


4.8 (123 reviews)

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Self-guided cycling

10 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

VIEW TRIP

Spain : Catalonia

Catalan Classic Walk

$1685


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

$1730

 
 

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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

$1895


4.8 (141 reviews)

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Self-guided walking

7 nights,
single centre

Level: 2
Moderate

Headwater
Navigation App

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France : The Dordogne

Dordogne Valleys & Villages Cycling

$1955


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

$1970


4.8 (90 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 : The Dordogne

Dordogne River Walk

$2000


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

$2105


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

$2150


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

$2375


4.4 (17 reviews)

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Self-guided cycling

6 nights,
hotel-to-hotel

Level: 3
Stretching

Headwater
Navigation App

VIEW TRIP

Italy : Puglia

Contrasts of Puglia Cycling

$2405


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

$2435


4.7 (91 reviews)

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Self-guided cycling

10 nights,
hotel-to-hotel

Level: 1
Leisurely

Headwater
Navigation App

VIEW TRIP

Portugal : Mainland Portugal

Porto Coastal Cycling

$2525


4.4 (59 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1
Leisurely

Headwater
Navigation App

VIEW TRIP

Croatia

Coastal Croatia - Porec to Pula Cycling

$2570


4.7 (86 reviews)

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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

$2825


4.8 (14 reviews)

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Self-guided walking

8 nights,
hotel-to-hotel

Level: 1
Leisurely

Printed route
directions

VIEW TRIP

Italy : Piedmont

Gastronomic Barolo Walk

$2915


4.9 (95 reviews)

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Self-guided walking

8 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

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Norway : Gudbrandsdalen

Cross-country skiing at Venabu

$3080


4.8 (293 reviews)

VIEW TRIP

Winter snow holiday

7 nights,
single centre



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Italy : Piedmont

Gastronomic Barolo Cycling by e-bike

$3260


4.8 (88 reviews)

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Self-guided cycling

8 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
Navigation App

VIEW TRIP

Spain : Catalonia

Catalan Classic Walk - Short Break

$1340


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

$1340


4.5 (11 reviews)

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Self-guided walking

7 nights,
twin centre

Level: 1 & 2

Headwater
Navigation App

VIEW TRIP

Italy : Veneto

Walking in the Prosecco Hills

$1370

NEW FOR 2025

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Self-guided walking

5 nights,
hotel-to-hotel

Level: 1+ & 2

Navigation App

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Italy : Tuscany

Treasures of Tuscany Walk: San Gimignano to Volterra

$1430

NEW FOR 2025

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Self-guided walking

7 nights,
twin centre

Level: 2+
Moderate plus

Headwater
Navigation App

VIEW TRIP

Holland

Cycling from Amsterdam

$1460

NEW FOR 2025

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Self-guided cycling

3 nights,
single centre

Level: 1+
Leisurely plus

Navigation App

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France : Burgundy

Cycling in Beaune Vineyards

$1460


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

$1490


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

$1520

 
 

VIEW TRIP

Self-guided cycling

3 nights,
single centre

Level: 2
Moderate

Navigation App

VIEW TRIP

Spain : Catalonia

Contrasts of Catalunya Cycling - Short Break

$1550


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

$1580

 
 

VIEW TRIP

Self-guided walking

4 nights,
hotel-to-hotel

Level: 1
Leisurely

Navigation App

VIEW TRIP

France : Burgundy

Tour de France - Burgundy

$1595

NEW FOR 2025

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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

$1595


4.8 (4 reviews)

VIEW TRIP

Winter snow holiday

5 nights,
single centre



VIEW TRIP

Switzerland : The Bernese Oberland

Cross country skiing in Kandersteg

$1595


4.7 (6 reviews)

VIEW TRIP

Winter snow holiday

7 nights,
single centre



VIEW TRIP

France : Alsace

Villages & Vineyards of Alsace- Short Break

$1610


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

$1610


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

$1625

NEW FOR 2025

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Self-guided cycling

3 nights,
hotel-to-hotel

Level: 3
Stretching

Navigation App

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Italy : The Dolomites

Cross country skiing in the Dolomites

$1625

NEW FOR 2025

VIEW TRIP

Winter snow holiday

7 nights,
single centre



VIEW TRIP

Austria : The Danube

Walking the Wachau Heritage Trail

$1670


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

$1700

NEW FOR 2025

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Self-guided walking

6 nights,
hotel-to-hotel

Level: 2
Moderate

Navigation App

VIEW TRIP

France : Burgundy

Classic Burgundy Cycling

$1715


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

$1730


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

$1745


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

$1760

 
 

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

$1790


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

$1805


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

$1805


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

$1805

 
 

VIEW TRIP

Self-guided cycling

5 nights,
single centre

Level: 1+
Leisurely plus

Headwater
Navigation App

VIEW TRIP

Greece

Walking on Kythnos Island - Premium

$1805


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

$1820


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

$1820

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

$1850

NEW FOR 2025

VIEW TRIP

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

$1895


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

$1895


4.9 (8 reviews)

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Self-guided walking

8 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
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France : Champagne

Cycle The Wine Route of Champagne

$1925

 
 

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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

$1940

 
 

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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

$1985


4.8 (4 reviews)

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Self-guided walking

7 nights,
twin centre

Level: 2
Moderate

Headwater
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Bosnia

Walking the Olympic Mountains of Bosnia

$1985

NEW FOR 2025

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
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France : Normandy

D-Day Beaches Of Normandy Cycling

$2000


4.6 (7 reviews)

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Self-guided cycling

5 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Printed route
directions

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Portugal : Mainland Portugal

Tour the Treasures of Portugal

$2000


4.8 (4 reviews)

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Self-guided cultural tour

7 nights,
twin centre



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Greece : Peloponnese

Peloponnese Coast and Mountain Walking

$2015

NEW FOR 2025

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
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Italy : Trentino

Wine & Walk in Chianti

$2015


4.0 (2 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Printed route
directions

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Greece : Crete

Cycling the Coast of Eastern Crete

$2030


4.4 (5 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 3
Stretching

Headwater
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United Kingdom : The Channel Islands

Walking in Jersey, Guernsey and Sark

$2030


4.4 (15 reviews)

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Self-guided walking

6 nights,
twin centre

Level: 1+ & 2

Headwater
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Italy : Umbria

Walking on the Francigena Way

$2030


4.6 (11 reviews)

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Self-guided pilgrimage

9 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
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France : Burgundy

Cycling The Grand Crus of Burgundy

$2075


5.0 (1 reviews)

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Self-guided cycling

6 nights,
twin centre

Level: 1+
Leisurely plus

Printed route
directions

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France : The Loire

Tour de France - Loire

$2120

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

$2120


4.8 (8 reviews)

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Self-guided walking

6 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
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France : Bordeaux

Cycling The Grand Crus of Bordeaux

$2135


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

$2150


4.9 (55 reviews)

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8 nights,
hotel-to-hotel

Printed route
directions



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France : The Loire

Cycling The UNESCO Loire Valley - Deluxe

$2150


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

$2180


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

$2195

 
 

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5 nights,
hotel-to-hotel

Navigation App



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France : Burgundy

Cycling the Vineyards From Beaune to Macon

$2195


4.8 (6 reviews)

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Self-guided cycling

6 nights,
hotel-to-hotel

Level: 1
Leisurely

Printed route
directions

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Ireland : County Wicklow

Unspoilt Ring of Kerry Cycling

$2195


4.4 (5 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
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France : The Loire

Cycling The Chateaux Of The Loire - Upgraded Short

$2210


4.8 (4 reviews)

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Self-guided cycling

5 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Navigation App

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Belgium

Cycling from Brussels to Bruges

$2225


4.0 (2 reviews)

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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

$2225

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

$2240


4.8 (6 reviews)

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Self-guided cultural tour

7 nights,
hotel-to-hotel



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France : The Loire

Cycling The Chateaux Of The Loire

$2255


4.5 (10 reviews)

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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

$2255


4.5 (6 reviews)

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Self-guided walking

8 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
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Spain : Rioja

Vineyards of La Rioja Cycling

$2270


4.6 (7 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
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France : Alsace

Villages & Vineyards of Alsace

$2270


4.4 (7 reviews)

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Self-guided walking

6 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
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France : The French Riviera

The French Riviera Golden Islands

$2270

NEW FOR 2025

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Self-guided walking

7 nights,
twin centre

Level: 1+
Leisurely plus

Printed route
directions

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France : Canal du Midi

Tour de France - Canal du Midi

$2285

NEW FOR 2025

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Self-guided cycling

4 nights,
hotel-to-hotel

Level: 3
Stretching

Navigation App

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France : The Dordogne

Dordogne Activities

$2285


4.8 (32 reviews)

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Multi-activity holiday

8 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
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Sweden : sweden

Cycling Stockholm's Archipelago

$2300


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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Spain : Balearic Islands

Walking Mallorca trails and traditional Fincas

$2315

NEW FOR 2025

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Navigation App

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France : Alsace

Cycling the Scenic Rhine: Strasbourg to Mainz

$2330

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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Portugal : The Algarve

Cycling the Algarve's Rota Vicentina

$2390


4.9 (9 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
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Italy : Tuscany

Cycling the hills of San Gimignano by E-bike

$2390

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

$2405


4.7 (3 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Printed route
directions

VIEW TRIP

Croatia

Hike, Bike & Paddle Croatia

$2420

NEW FOR 2025

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Multi-activity holiday

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
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Spain : Extremadura

Cycling Central Spain in Style

$2435

NEW FOR 2025

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
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France : Atlantic Coast

Tour de France - Atlantic Coast

$2450

NEW FOR 2025

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Self-guided cycling

5 nights,
hotel-to-hotel

Level: 2 & 2+

Navigation App

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Italy : Piedmont

Walking the Wine Villages of Piedmont

$2450


4.5 (4 reviews)

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Self-guided walking

8 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
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Holland

Cycling from Amsterdam to Brussels

$2480


5.0 (3 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Navigation App

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Italy : Sardinia

Undiscovered Sardinia Cycling

$2525


4.7 (19 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Navigation App

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United Kingdom : The Channel Islands

Walking in Jersey, Guernsey and Sark Premium

$2555


5.0 (2 reviews)

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Self-guided walking

6 nights,
twin centre

Level: 1+
Leisurely plus

Headwater
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Italy : Emilia Romagna

Emilia Romagna: Bologna to Parma Cycling

$2570


4.7 (3 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Navigation App

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Italy : Sicily

Sicily: Vino & Volcanoes

$2615


5.0 (2 reviews)

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Self-guided cultural tour

7 nights,
hotel-to-hotel

Headwater
Navigation App

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Greece : Crete

Walking the Wonders of Crete

$2615

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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France : Normandy

Paris to the Sea Along the Seine River

$2750

NEW FOR 2025

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Printed route
directions

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France : The Loire

Cycling The Chateaux Of The Loire - Upgraded

$2780


4.7 (7 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Navigation App

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Italy : Piedmont

Cycling the Wine Villages of Piedmont by e-bike

$2795


4.8 (5 reviews)

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Self-guided cycling

8 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
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France : Provence

Provence Velo Vin Voyage

$2795


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

$2885


4.9 (34 reviews)

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Self-guided walking

10 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

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Sweden : sweden

Stockholm to Copenhagen Cycling

$2915


4.3 (4 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

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France : Corsica

Corsica with Ebike

$2930


4.7 (3 reviews)

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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

$2945


4.8 (56 reviews)

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Self-guided cycling

9 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
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Denmark

Nordic Cities by Rail

$2945

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

$2975


4.9 (13 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
Navigation App

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Italy : Italian Lakes

Cycling the Italian Lakes

$2990


4.8 (5 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
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Italy

Highlights of Puglia Cycling

$3290


4.8 (13 reviews)

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Self-guided cycling

10 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

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Norway : Gudbrandsdalen

Guided Walking in Venabu

$3680


4.8 (15 reviews)

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Guided group walking

7 nights,
single centre

Level: 2+
Moderate plus

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USA : Maine

Cycling Maine's Coast & National Park

$5000

 
 

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
Navigation App

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China

Walking the Charms of China - With Private Guide

$5120

 
 

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Private guided walking

10 nights,
hotel-to-hotel

Level: 2+
Moderate plus

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Japan

Shikoku Pilgrimage Trail

$5195


5.0 (1 reviews)

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Self-guided pilgrimage

10 nights,
hotel-to-hotel

Level: 3
Stretching

Printed route
directions

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Japan

Walk the Kumano Kodo

$5240


5.0 (4 reviews)

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Self-guided walking

10 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Printed route
directions

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Japan

Walk the Nakasendo Trail

$5300

 
 

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Self-guided walking

10 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Printed route
directions

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Japan

Japan: Hiroshima & Island Hopping

$5450

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

$975

 
 

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Guided group walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Printed route
directions

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Cyprus

Walking in North Cyprus

$1425


4.0 (1 reviews)

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Guided group walking

7 nights,
single centre

Printed route
directions

Operated by
Exodus Travels

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Greece

Mountains & Villages of Evia

$1650


4.8 (4 reviews)

VIEW TRIP

Guided group walking

7 nights,
single centre

Level: 2+
Moderate plus

Printed route
directions

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Spain : Mallorca

Walking in Mallorca

$2100


5.0 (6 reviews)

VIEW TRIP

Guided group walking

7 nights,
twin centre

Level: 2
Moderate

Printed route
directions

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Greece

Walking on the Greek Islands

$2175

 
 

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Guided group walking

7 nights,
hotel-to-hotel

Level: 1
Leisurely

Printed route
directions

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Italy : Puglia

Walking in Puglia & Matera

$2250


4.3 (12 reviews)

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Guided group walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Printed route
directions

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Italy : Sardinia

Walking in Sardinia

$2250


5.0 (1 reviews)

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Guided group walking

7 nights,
single centre

Level: 3
Stretching

Printed route
directions

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Italy : The Dolomites

Snowshoeing in the Dolomites - Premium Adventure

$2550

 
 

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Winter snow holiday

7 nights,
single centre

Printed route
directions

Operated by
Exodus Travels

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Italy : The Dolomites

Classic Dolomites - Premium

$3150


5.0 (1 reviews)

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Guided group walking

7 nights,
single centre

Level: 3
Stretching

Printed route
directions

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Portugal : Mainland Portugal

Portugal: Walking & Wine - Premium Adventure

$3600


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

$4050

 
 

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Guided group cycling

11 nights,
hotel-to-hotel

Level: 3
Stretching

Printed route
directions

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Costa Rica

Discover Costa Rica

$4575

 
 

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Guided group walking

14 nights,
hotel-to-hotel

Level: 1
Leisurely

Printed route
directions

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Costa Rica

Costa Rica's Coastal Secrets

$5550

 
 

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Guided group walking

14 nights,
hotel-to-hotel

Level: 2
Moderate

Printed route
directions

VIEW TRIP

Thailand

Cycle Indochina & Angkor - Premium Adventure

$6225

 
 

VIEW TRIP

Guided group cycling

13 nights,
hotel-to-hotel

Level: 3
Stretching

Printed route
directions

VIEW TRIP

Peru

Peru Explorer

$7050

 
 

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Guided group walking

19 nights,
hotel-to-hotel

Level: 2
Moderate

Printed route
directions

VIEW TRIP

Japan

Japan's Kumano Kodo

$8025

 
 

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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

$10800

 
 

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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.