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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

£909


4.7 (40 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
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Denmark

Cycling from Copenhagen

£919


5.0 (1 reviews)

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Self-guided cycling

4 nights,
single centre

Level: 1
Leisurely

Headwater
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Albania

E-bike Across Southern Albania

£1089

NEW FOR 2025

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
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Italy : Umbria

The Wine Trails of Umbria Cycling

£1129


5.0 (1 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
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Greece

Cycling in the Peloponnese

£1239


4.8 (11 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
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United Kingdom : The Channel Islands

Cycling in Jersey, Guernsey and Sark

£1399


4.0 (1 reviews)

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Self-guided cycling

6 nights,
twin centre

Level: 1+
Leisurely plus

Headwater
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Portugal : Mainland Portugal

Cycling in the Douro Valley

£1419

 
 

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 3
Stretching

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Italy : Puglia

Cycling the Heel of Italy - Matera to Lecce

£1459


4.6 (10 reviews)

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Self-guided cycling

11 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
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Portugal : Mainland Portugal

Coimbra to Lisbon Cycling

£1889

NEW FOR 2025

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Self-guided cycling

11 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

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Italy : Veneto

Heart of Veneto Cycling

£939


4.8 (72 reviews)

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Self-guided cycling

7 nights,
single centre

Level: 1
Leisurely

Headwater
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Italy : Veneto

Venetian Villas and Vineyards Cycling

£1079


4.7 (57 reviews)

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Self-guided cycling

8 nights,
hotel-to-hotel

Level: 1
Leisurely

Headwater
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Italy : Sicily

Secrets of Sicily Cycling

£1159


4.6 (22 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

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Italy : Tuscany

A Taste of Tuscany Cycling

£1219


4.9 (27 reviews)

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Self-guided cycling

7 nights,
single centre

Level: 2+
Moderate plus

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Portugal : The Algarve

Cycling in The Real Algarve

£1279


4.7 (61 reviews)

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Self-guided cycling

6 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
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France : Provence

Cotes du Ventoux Cycling

£1289


4.8 (36 reviews)

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Self-guided cycling

6 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

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Italy : Sicily

Cycling through Baroque Sicily

£1479


4.4 (20 reviews)

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Self-guided cycling

8 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
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France

Landscapes of the Luberon Cycling

£1579


4.4 (21 reviews)

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Self-guided cycling

8 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
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Slovenia

Julian Alps to the Adriatic Cycling

£1889


4.8 (118 reviews)

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Self-guided cycling

10 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

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France : The Dordogne

Dordogne Valleys & Villages Cycling

£1069


4.7 (42 reviews)

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Self-guided cycling

8 nights,
hotel-to-hotel

Level: 2
Moderate

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Spain : Catalonia

Contrasts of Catalunya Cycling

£1109


4.7 (53 reviews)

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Self-guided cycling

6 nights,
hotel-to-hotel

Level: 1
Leisurely

Headwater
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Spain : Balearic Islands

Cycling in Mallorca: Coast to Coast

£1179


4.7 (25 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
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Italy : Puglia

Contrasts of Puglia Cycling

£1279


4.6 (123 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
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Spain : Andalucia

Cycling in Andalucia: Seville to Cadiz

£1349


4.3 (12 reviews)

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Self-guided cycling

6 nights,
hotel-to-hotel

Level: 3
Stretching

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Austria : Carinthia

Lake Constance Cycling

£1389


4.7 (88 reviews)

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Self-guided cycling

10 nights,
hotel-to-hotel

Level: 1
Leisurely

Headwater
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United Kingdom : Norfolk

Contrasts of Norfolk Cycling

£1449


5.0 (1 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
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Portugal : Mainland Portugal

Porto Coastal Cycling

£1449


4.4 (59 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1
Leisurely

Headwater
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Croatia

Coastal Croatia - Porec to Pula Cycling

£1479


4.7 (85 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
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Italy : Piedmont

Gastronomic Barolo Cycling by e-bike

£2299


4.8 (88 reviews)

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Self-guided cycling

8 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
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Spain : Catalonia

Contrasts of Catalunya Cycling - Short Break

£799


4.6 (5 reviews)

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Self-guided cycling

4 nights,
hotel-to-hotel

Level: 1
Leisurely

Headwater
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Italy : Italian Lakes

Cycling Lake Garda with e-bike

£929


4.5 (2 reviews)

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Self-guided cycling

6 nights,
single centre

Level: 2+
Moderate plus

Headwater
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Sweden : sweden

Cycling from Stockholm

£959

 
 

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Self-guided cycling

5 nights,
single centre

Level: 1+
Leisurely plus

Headwater
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France : Provence

Hilltop Villages of Provence Cycling - Short Break

£969


4.9 (7 reviews)

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Self-guided cycling

4 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
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Austria : Lake Constance

Highlights of Lake Constance by bike

£1059


4.9 (26 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1
Leisurely

Headwater
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Spain : Catalonia

Classic Catalan Cycling

£1059


4.8 (11 reviews)

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Self-guided cycling

8 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
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Greece

Cycling the Coast of Eastern Crete

£1119


4.0 (2 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 3
Stretching

Headwater
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United Kingdom : Norfolk

Highlights of Norfolk Cycling

£1139


4.3 (10 reviews)

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Self-guided cycling

5 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
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Spain : Valencia

Cycling Valencia and the Orange Blossom Coast

£1149


4.5 (8 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
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Spain : Andalucia

E-biking in Andalucia: Sierra de Aracena

£1179

NEW FOR 2025

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
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France : Provence

Hilltop Villages of Provence Cycling

£1209


4.8 (16 reviews)

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Self-guided cycling

6 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
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Ireland

Unspoilt Ring of Kerry Cycling

£1229


4.4 (5 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
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Spain : Rioja

Vineyards of La Rioja Cycling

£1279


4.6 (7 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
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Sweden : sweden

Cycling Stockholm's Archipelago

£1289


5.0 (1 reviews)

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Self-guided cycling

6 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
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Portugal : The Algarve

Cycling the Algarve's Rota Vicentina

£1289


4.9 (8 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

£1359

NEW FOR 2025

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Self-guided cycling

7 nights,
single centre

Level: 2+ & 3

Headwater
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Portugal : The Azores

Azores By E-bike

£1369


4.0 (4 reviews)

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Self-guided cycling

6 nights,
hotel-to-hotel

Level: 3
Stretching

Headwater
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Spain : Extremadura

Cycling Central Spain in Style

£1389

NEW FOR 2025

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
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Portugal : Mainland Portugal

Cycling in Portugal: From the Mountains to the Sea

£1429


4.5 (16 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
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United Kingdom : The Cotswolds

Best of the Cotswolds Cycling

£1619


4.0 (1 reviews)

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Self-guided cycling

6 nights,
twin centre

Level: 2
Moderate

Headwater
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France : Provence

Vineyards of Vaucluse Cycling

£1629


4.8 (18 reviews)

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Self-guided cycling

8 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
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Italy : Italian Lakes

Cycling the Italian Lakes

£1649


4.0 (1 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
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Sweden : sweden

Stockholm to Copenhagen Cycling

£1709


4.3 (3 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
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Portugal : Mainland Portugal

Porto to Coimbra Cycling

£1729


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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Slovenia

Secrets of Slovenia Cycling

£1759


4.9 (11 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
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Italy : Puglia

Highlights of Puglia Cycling

£1869


4.8 (11 reviews)

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Self-guided cycling

10 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
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Italy : Piedmont

Cycling the Wine Villages of Piedmont by e-bike

£2199


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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USA : Maine

Cycling Maine's Coast & National Park

£3039

 
 

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
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Canada : Sunshine Coast

Walk & Paddle Canada’s Sunshine Coast

£2609

NEW FOR 2025

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Multi-activity holiday

8 nights,
hotel-to-hotel

Level: 1+ to 3

Headwater
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Austria : Salzburg

Austrian Lakes Activities

£1079


4.8 (68 reviews)

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Multi-activity holiday

7 nights,
single centre

Level: 1
Leisurely

Headwater
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Spain : Catalonia

Catalonia Activities

£759


4.5 (13 reviews)

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Multi-activity holiday

7 nights,
single centre

Level: 1
Leisurely

Headwater
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France : The Dordogne

Dordogne Activities

£1289


4.8 (31 reviews)

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Multi-activity holiday

8 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
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Spain : Galicia

Cycling the Camino de Santiago

£1479


4.5 (6 reviews)

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Self-guided cycling

8 nights,
hotel-to-hotel

Level: 3
Stretching

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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.