Cycling holidays with GPS routes

Showing 61 out of 337 trips

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

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

Find out about the benefits of GPS route navigation to see how our relaxed cycling holidays are now even better!

Italy : Puglia

Cycling the Heel of Italy - Alberobello to Lecce

NZ$2000


4.7 (40 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

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Denmark

Cycling from Copenhagen

NZ$2025


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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Albania

E-bike Across Southern Albania

NZ$2400

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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Italy : Umbria

The Wine Trails of Umbria Cycling

NZ$2485


5.0 (1 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

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Greece

Cycling in the Peloponnese

NZ$2730


4.8 (11 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

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United Kingdom : The Channel Islands

Cycling in Jersey, Guernsey and Sark

NZ$3080


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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Portugal : Mainland Portugal

Cycling in the Douro Valley

NZ$3125

 
 

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 3
Stretching

Headwater
Navigation App

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Italy : Puglia

Cycling the Heel of Italy - Matera to Lecce

NZ$3210


4.6 (10 reviews)

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Self-guided cycling

11 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

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Portugal : Mainland Portugal

Coimbra to Lisbon Cycling

NZ$4160

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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Italy : Veneto

Heart of Veneto Cycling

NZ$2070


4.8 (72 reviews)

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Self-guided cycling

7 nights,
single centre

Level: 1
Leisurely

Headwater
Navigation App

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Italy : Veneto

Venetian Villas and Vineyards Cycling

NZ$2375


4.7 (57 reviews)

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Self-guided cycling

8 nights,
hotel-to-hotel

Level: 1
Leisurely

Headwater
Navigation App

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Italy : Sicily

Secrets of Sicily Cycling

NZ$2550


4.6 (22 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

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Italy : Tuscany

A Taste of Tuscany Cycling

NZ$2685


4.9 (27 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

NZ$2815


4.7 (61 reviews)

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Self-guided cycling

6 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

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France : Provence

Cotes du Ventoux Cycling

NZ$2840


4.8 (36 reviews)

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Self-guided cycling

6 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

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Italy : Sicily

Cycling through Baroque Sicily

NZ$3255


4.4 (20 reviews)

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Self-guided cycling

8 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

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France

Landscapes of the Luberon Cycling

NZ$3475


4.4 (21 reviews)

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Self-guided cycling

8 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

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Slovenia

Julian Alps to the Adriatic Cycling

NZ$4160


4.8 (118 reviews)

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Self-guided cycling

10 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

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France : The Dordogne

Dordogne Valleys & Villages Cycling

NZ$2355


4.7 (42 reviews)

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Self-guided cycling

8 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

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Spain : Catalonia

Contrasts of Catalunya Cycling

NZ$2375


4.7 (53 reviews)

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Self-guided cycling

6 nights,
hotel-to-hotel

Level: 1
Leisurely

Headwater
Navigation App

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Spain : Balearic Islands

Cycling in Mallorca: Coast to Coast

NZ$2595


4.7 (25 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

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Italy : Puglia

Contrasts of Puglia Cycling

NZ$2815


4.6 (123 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

Cycling in Andalucia: Seville to Cadiz

NZ$2970


4.3 (12 reviews)

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Self-guided cycling

6 nights,
hotel-to-hotel

Level: 3
Stretching

Headwater
Navigation App

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Austria : Carinthia

Lake Constance Cycling

NZ$3060


4.7 (88 reviews)

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Self-guided cycling

10 nights,
hotel-to-hotel

Level: 1
Leisurely

Headwater
Navigation App

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United Kingdom : Norfolk

Contrasts of Norfolk Cycling

NZ$3190


5.0 (1 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

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Portugal : Mainland Portugal

Porto Coastal Cycling

NZ$3190


4.4 (59 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1
Leisurely

Headwater
Navigation App

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Croatia

Coastal Croatia - Porec to Pula Cycling

NZ$3255


4.7 (85 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

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Italy : Piedmont

Gastronomic Barolo Cycling by e-bike

NZ$5060


4.8 (88 reviews)

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Self-guided cycling

8 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
Navigation App

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Spain : Catalonia

Contrasts of Catalunya Cycling - Short Break

NZ$2905


4.6 (5 reviews)

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Self-guided cycling

4 nights,
hotel-to-hotel

Level: 1
Leisurely

Headwater
Navigation App

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Italy : Italian Lakes

Cycling Lake Garda with e-bike

NZ$2045


4.5 (2 reviews)

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Self-guided cycling

6 nights,
single centre

Level: 2+
Moderate plus

Headwater
Navigation App

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Sweden : sweden

Cycling from Stockholm

NZ$135

 
 

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Self-guided cycling

5 nights,
single centre

Level: 1+
Leisurely plus

Headwater
Navigation App

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France : Provence

Hilltop Villages of Provence Cycling - Short Break

NZ$2135


4.9 (7 reviews)

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Self-guided cycling

4 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
Navigation App

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Austria : Lake Constance

Highlights of Lake Constance by bike

NZ$2330


4.9 (26 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1
Leisurely

Headwater
Navigation App

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Spain : Catalonia

Classic Catalan Cycling

NZ$2330


4.8 (11 reviews)

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Self-guided cycling

8 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

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Greece

Cycling the Coast of Eastern Crete

NZ$2465


4.0 (2 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 3
Stretching

Headwater
Navigation App

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United Kingdom : Norfolk

Highlights of Norfolk Cycling

NZ$2510


4.3 (10 reviews)

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Self-guided cycling

5 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

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Spain : Valencia

Cycling Valencia and the Orange Blossom Coast

NZ$2530


4.5 (8 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

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Spain : Andalucia

E-biking in Andalucia: Sierra de Aracena

NZ$2595

NEW FOR 2025

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

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France : Provence

Hilltop Villages of Provence Cycling

NZ$2660


4.8 (16 reviews)

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Self-guided cycling

6 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
Navigation App

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Ireland

Unspoilt Ring of Kerry Cycling

NZ$2705


4.4 (5 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

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Spain : Rioja

Vineyards of La Rioja Cycling

NZ$2815


4.6 (7 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

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Sweden : sweden

Cycling Stockholm's Archipelago

NZ$2840


5.0 (1 reviews)

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Self-guided cycling

6 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

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Portugal : The Algarve

Cycling the Algarve's Rota Vicentina

NZ$2840


4.9 (8 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
Navigation App

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Italy : Tuscany

Cycling the hills of San Gimignano by E-bike

NZ$2990

NEW FOR 2025

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Self-guided cycling

7 nights,
single centre

Level: 2+ & 3

Headwater
Navigation App

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Portugal : The Azores

Azores By E-bike

NZ$3015


4.0 (4 reviews)

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Self-guided cycling

6 nights,
hotel-to-hotel

Level: 3
Stretching

Headwater
Navigation App

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Spain : Extremadura

Cycling Central Spain in Style

NZ$3060

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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Portugal : Mainland Portugal

Cycling in Portugal: From the Mountains to the Sea

NZ$3145


4.5 (16 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

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United Kingdom : The Cotswolds

Best of the Cotswolds Cycling

NZ$3565


4.0 (1 reviews)

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Self-guided cycling

6 nights,
twin centre

Level: 2
Moderate

Headwater
Navigation App

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France : Provence

Vineyards of Vaucluse Cycling

NZ$3585


4.8 (18 reviews)

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Self-guided cycling

8 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

VIEW TRIP

Italy : Italian Lakes

Cycling the Italian Lakes

NZ$3630


4.0 (1 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

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Sweden : sweden

Stockholm to Copenhagen Cycling

NZ$3760


4.3 (3 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

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Portugal : Mainland Portugal

Porto to Coimbra Cycling

NZ$3805


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

Slovenia

Secrets of Slovenia Cycling

NZ$3870


4.9 (11 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
Navigation App

VIEW TRIP

Italy : Puglia

Highlights of Puglia Cycling

NZ$4115


4.8 (11 reviews)

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Self-guided cycling

10 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

VIEW TRIP

Italy : Piedmont

Cycling the Wine Villages of Piedmont by e-bike

NZ$4840


4.8 (5 reviews)

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Self-guided cycling

8 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
Navigation App

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USA : Maine

Cycling Maine's Coast & National Park

NZ$6690

 
 

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
Navigation App

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Canada : Sunshine Coast

Walk & Paddle Canada’s Sunshine Coast

NZ$5740

NEW FOR 2025

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Multi-activity holiday

8 nights,
hotel-to-hotel

Level: 1+ to 3

Headwater
Navigation App

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Austria : Salzburg

Austrian Lakes Activities

NZ$2375


4.8 (68 reviews)

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Multi-activity holiday

7 nights,
single centre

Level: 1
Leisurely

Headwater
Navigation App

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Spain : Catalonia

Catalonia Activities

NZ$1670


4.5 (13 reviews)

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Multi-activity holiday

7 nights,
single centre

Level: 1
Leisurely

Headwater
Navigation App

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France : The Dordogne

Dordogne Activities

NZ$2840


4.8 (31 reviews)

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Multi-activity holiday

8 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

Spain : Galicia

Cycling the Camino de Santiago

NZ$3255


4.5 (6 reviews)

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Self-guided cycling

8 nights,
hotel-to-hotel

Level: 3
Stretching

Headwater
Navigation App

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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.