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Showing 60 out of 338 trips

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

£929


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

£1259


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

£1389


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

Headwater
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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

Headwater
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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

Headwater
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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

Headwater
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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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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 : Provence

Cotes du Ventoux Cycling

£1729


4.8 (36 reviews)

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Self-guided cycling

6 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

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

Headwater
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France : Provence

Landscapes of the Luberon Cycling

£2039


4.4 (21 reviews)

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Self-guided cycling

8 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
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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

Headwater
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Spain : Catalonia

Contrasts of Catalunya Cycling

£1079


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

Headwater
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United Kingdom : Norfolk

Contrasts of Norfolk Cycling

£1379


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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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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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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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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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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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

£1229


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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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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Spain : Catalonia

Contrasts of Catalunya Cycling - Short Break

£1319


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 : 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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France : Provence

Hilltop Villages of Provence Cycling - Short Break

£1379


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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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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United Kingdom : Norfolk

Highlights of Norfolk Cycling

£1429


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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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

£1559


4.0 (1 reviews)

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Self-guided cycling

6 nights,
twin centre

Level: 2
Moderate

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
Navigation App

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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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France : Provence

Vineyards of Vaucluse Cycling

£2019


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 : 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
Navigation App

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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
Navigation App

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Spain : Catalonia

Catalonia Activities

£839


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

Headwater
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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.