The Winter Sun Collection

As the winter weather rolls in, there’s no need to get summer blues when you can get winter sun instead. Our holidays to hot destinations will keep you in shorts and flip-flops instead of hats and scarves. From the pink sand beaches of Bermuda to the colourful towns of the Amalfi Coast , our selection of active cycling and walking holidays below are all guaranteed to keep you in the heat.

 

Malta + Gozo

Highlights of Secrets of Malta Walking

£589


4.5 (2 reviews)

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Self-guided walking

4 nights,
single centre

Level: 2
Moderate

Headwater
Navigation App

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Spain : The Canary Islands

Walk the Bonita Island of La Palma

£799

NEW FOR 2026

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Self-guided walking

7 nights,
single centre

Level: 2+ & 3

Headwater
Navigation App

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Malta + Gozo

Discovering the Maltese Islands

£809


4.3 (10 reviews)

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Self-guided walking

7 nights,
twin centre

Level: 2
Moderate

Headwater
Navigation App

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Spain : The Canary Islands

Contrasts of Lanzarote

£919


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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Spain : Andalucia

Walking in Sierra de Aracena

£949


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 : The Canary Islands

Walking the trails of Tenerife

£959


4.5 (4 reviews)

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Self-guided walking

7 nights,
single centre

Level: 2 & 3

Headwater
Navigation App

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Spain : The Canary Islands

Walking in Fuerteventura along the GR 131

£1029


5.0 (2 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 2 & 2+

Headwater
Navigation App

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Italy : Puglia

Cycling the Heel of Italy - Alberobello to Lecce

£1039


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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Portugal : Madeira

Walking the Waterways and villages of Madeira

£1079


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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Spain : The Canary Islands

Contrasts of La Gomera

£1089


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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Italy : Puglia

Journey through Puglia to Matera

£1129


4.8 (15 reviews)

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Cultural tour

7 nights,
hotel-to-hotel

Headwater
Navigation App

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Spain : The Canary Islands

Walking on Gran Canaria

£1129


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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Spain : The Canary Islands

Volcanoes and Vineyards of Lanzarote

£1139


4.4 (7 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 1 to 2+

Headwater
Navigation App

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Portugal : The Algarve

Walking Rota Vicentina North Fishermen's Trail

£1209


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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Spain : The Canary Islands

Walking across La Gomera

£1219

NEW FOR 2026

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 2 & 3

Headwater
Navigation App

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Italy : Puglia

Cycling the Heel of Italy - Matera to Lecce

£1639


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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Spain : The Canary Islands

Contrasts of Tenerife Walk (with transfers)

£1969

 
 

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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

£1989

 
 

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Self-guided cycling

11 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

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Spain : The Canary Islands

Contrasts of Tenerife Walk (with car hire)

£1299


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

£829


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 : Veneto

Bolzano, Verona & Venice Ride

£1129


4.7 (20 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Navigation App

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Italy : Puglia

Self Guided Walking in Puglia: From Lecce to Matera

£1169


4.7 (65 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 1
Leisurely

Headwater
Navigation App

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Italy : Tuscany

A Taste of Tuscany Walking

£1269


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

£1319


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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Portugal : The Algarve

Cycling in The Real Algarve

£1399


4.7 (66 reviews)

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Self-guided cycling

6 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

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Bermuda

Islands of Bermuda Walk

£1409


4.6 (38 reviews)

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Self-guided walking

7 nights,
single centre

Level: 1
Leisurely

Headwater
Navigation App

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Portugal : Madeira

Marvels of Madeira Walk

£1489


4.7 (126 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

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Portugal : The Algarve

Walk the Algarve's Wild West

£1169


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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Austria : The Danube

Cycling from Vienna to Budapest

£1189


4.6 (66 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Navigation App

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Spain : Balearic Islands

Cycling in Mallorca: Coast to Coast

£1299


4.7 (35 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

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Spain : Andalucia

Cycling in Andalucia: Seville to Cadiz

£1449


4.4 (17 reviews)

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Self-guided cycling

6 nights,
hotel-to-hotel

Level: 3
Stretching

Headwater
Navigation App

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Italy : Puglia

Contrasts of Puglia Cycling

£1449


4.6 (125 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

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Spain : Andalucia

Hidden Valleys of Cordoba Walk

£579


4.8 (55 reviews)

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Self-guided walking

7 nights,
single centre

Level: 2
Moderate

Headwater
Navigation App

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Cyprus

Walking the Akamas Peninsula

£759


4.5 (11 reviews)

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Self-guided walking

7 nights,
twin centre

Level: 1 & 2

Headwater
Navigation App

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Malta + Gozo : Malta

Secrets of Malta Walking

£759


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 : Veneto

Walking in the Prosecco Hills

£779

NEW FOR 2026

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Self-guided walking

5 nights,
hotel-to-hotel

Level: 1+ & 2

Navigation App

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Italy : Liguria

Walking in the Cinque Terre and Portofino

£859


4.3 (7 reviews)

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Self-guided walking

6 nights,
single centre

Level: 2
Moderate

Navigation App

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Portugal : Madeira

Walk the Garden Island of Madeira

£859


4.8 (4 reviews)

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Self-guided walking

7 nights,
single centre

Level: 2
Moderate

Headwater
Navigation App

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Cyprus

Contrasts of Cyprus Walking

£859


4.6 (8 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 1+ to 2+

Headwater
Navigation App

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Italy

Undiscovered Puglia Walk - Discovering the South-East Coast

£899


4.8 (13 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

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Italy : Istria

Walking the Highlights of Istria: Italy, Slovenia & Croatia

£1059


5.0 (2 reviews)

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Self-guided walking

6 nights,
hotel-to-hotel

Level: 2
Moderate

Navigation App

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Italy : Tuscany

Cycling in Tuscany: Pisa to Florence

£1109


4.7 (9 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Navigation App

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Austria : The Danube

Cycling along the Danube from Passau to Vienna

£1119


4.9 (28 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Navigation App

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Spain : Balearic Islands

Walking Mallorca trails and traditional Fincas

£1179

 
 

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Navigation App

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Italy : Campania

Coastal Cilento Walk

£1199


4.9 (9 reviews)

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Self-guided walking

8 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
Navigation App

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Italy : Italian Lakes

Cycling Lake Garda by e-bike

£1209


4.6 (5 reviews)

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Self-guided cycling

6 nights,
single centre

Level: 2+
Moderate plus

Headwater
Navigation App

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Spain

Walking in El Hierro

£1209


4.5 (4 reviews)

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Self-guided walking

7 nights,
single centre

Level: 1 to 2+

Headwater
Navigation App

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Italy : The Bay of Naples

Gems of the Amalfi Coast Walking

£1229


4.8 (5 reviews)

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Self-guided walking

7 nights,
twin centre

Level: 2
Moderate

Headwater
Navigation App

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France : The French Riviera

The French Riviera Golden Islands

£1239

NEW FOR 2026

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Self-guided walking

7 nights,
twin centre

Level: 1+ & 2

Headwater
Navigation App

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Italy : Umbria

Walking on the Francigena Way

£1249


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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Spain : The Canary Islands

Highlights of El Hierro Walk

£1339


4.9 (11 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 2+ & 3

Headwater
Navigation App

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Italy : Sardinia

Undiscovered Sardinia Cycling

£1389


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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Portugal : The Algarve

Cycling the Algarve's Rota Vicentina

£1419


4.9 (9 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
Navigation App

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Spain : Extremadura

Cycling Central Spain in Style

£1489


4.5 (2 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
Navigation App

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Austria : The Danube

Passau to Vienna Cycling

£1499


4.8 (77 reviews)

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Self-guided cycling

10 nights,
hotel-to-hotel

Level: 1
Leisurely

Navigation App

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Cape Verde

Cape Verde's Northern Islands - With Private Guide

£1709


4.9 (7 reviews)

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Private guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

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Portugal : The Algarve

Walking the Algarve's South West

£1719


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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Italy : Italian Lakes

Cycling the Italian Lakes

£1859


4.9 (9 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

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Morocco

Morocco: Mountains, Desert & Coast

£2019

 
 

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Cultural tour

7 nights,
hotel-to-hotel



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Italy : Puglia

Highlights of Puglia Cycling

£2079


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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Japan

Shikoku Pilgrimage Trail

£3329


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

£3359


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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China

Walking the Charms of China - With Private Guide

£3499

 
 

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Private guided walking

10 nights,
hotel-to-hotel

Level: 2+
Moderate plus

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Japan

Walk the Nakasendo Trail

£3619

 
 

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Self-guided walking

10 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Printed route
directions

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Japan

Exploring the land of Shogun and Samurai

£3879

NEW FOR 2026

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Cultural tour

10 nights,
hotel-to-hotel

8 meals
included

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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.

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