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

$1565


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

$1580


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

$1835

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

$1895


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

$2060


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

$2300


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

$2330

 
 

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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

$2390


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

$3035

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

$1610


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

$1820


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

$1940


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

$2030


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

$2120


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

$2135


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

$2420


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

$2570


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

$3035


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

$1805


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

$1820


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

$1970


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

$2120


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

$2225


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

$2285


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

$2375


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

$2375


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

$2420


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

$3650


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

$2180


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

$1595


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

$290

 
 

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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

$1655


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

$1790


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

$1790


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

$1880


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

$1910


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

$1925


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

$1970

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

$2015


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

$2045


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

$2120


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

$2135


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

$2135


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

$2240

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

$2255


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

$2285

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

$2345


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

$2630


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

$2645


4.8 (18 reviews)

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Self-guided cycling

8 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

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Italy : Italian Lakes

Cycling the Italian Lakes

$2675


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

$2765


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

$2795


4.8 (56 reviews)

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Self-guided cycling

9 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

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Slovenia

Secrets of Slovenia Cycling

$2840


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

$3005


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

$3500


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

$4760

 
 

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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

$4115

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

$1820


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

$1340


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

$2135


4.8 (31 reviews)

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Multi-activity holiday

8 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

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Spain : Galicia

Cycling the Camino de Santiago

$2420


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.