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Showing 67 out of 337 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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Italy : The Dolomites

Cycling from the Dolomites to Venice

£1009


4.8 (6 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Navigation App

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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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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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France : Atlantic Coast

Cycling along the Atlantic Coast

£1739

NEW FOR 2025

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Printed route
directions

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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 : Trentino

Brenner Pass to Venice Cycling

£1899


5.0 (2 reviews)

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Self-guided cycling

9 nights,
hotel-to-hotel

Level: 2
Moderate

Navigation App

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Norway

Cycling in the Lofoten Islands

£3469


5.0 (2 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Navigation App

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France : Provence

Hilltop Villages of Provence with e-bike

£1629


4.0 (2 reviews)

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Self-guided cycling

7 nights,
twin centre

Level: 1+ & 2

Printed route
directions

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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

Bolzano, Verona & Venice Ride

£1079


4.7 (18 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Printed route
directions

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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 : 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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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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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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France : Burgundy

Cycling in Beaune Vineyards

£739


5.0 (1 reviews)

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Self-guided cycling

4 nights,
single centre

Level: 1+
Leisurely plus

Printed route
directions

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France : Champagne

Cycling the Vineyards of Champagne

£779

 
 

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Self-guided cycling

3 nights,
single centre

Level: 2
Moderate

Navigation App

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France : Provence

Tour de France - Provence

£849

NEW FOR 2025

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Self-guided cycling

3 nights,
hotel-to-hotel

Level: 3
Stretching

Printed route
directions

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France : Burgundy

Classic Burgundy Cycling

£909


4.0 (1 reviews)

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Self-guided cycling

4 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Printed route
directions

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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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France : The Loire

Cycling In The Royal Loire Valley

£959

 
 

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Self-guided cycling

3 nights,
single centre

Level: 1
Leisurely

Navigation App

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Italy : Veneto

Adriatic Coast - Venice to Poreč Ride

£959

NEW FOR 2025

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Navigation App

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France : The Loire

Cycling The Chateaux Of The Loire - Short Break

£969


4.8 (6 reviews)

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Self-guided cycling

5 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Navigation App

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France : The Loire

Cycling The UNESCO Loire Valley

£969


5.0 (3 reviews)

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Self-guided cycling

5 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Navigation App

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France : Alsace

Cycling the Wine Route of Alsace

£1029


4.8 (9 reviews)

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Self-guided cycling

5 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Navigation App

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France : Burgundy

Cycling The Grand Crus of Burgundy

£1119


5.0 (1 reviews)

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Self-guided cycling

6 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Printed route
directions

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France : Champagne

Cycle The Wine Route of Champagne

£1139

 
 

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Self-guided cycling

5 nights,
twin centre

Level: 2+ & 3

Navigation App

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France : The Loire

Tour de France - Loire

£1179

NEW FOR 2025

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Self-guided cycling

5 nights,
hotel-to-hotel

Level: 3
Stretching

Navigation App

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France : Bordeaux

Cycling The Grand Crus of Bordeaux

£1189


4.5 (4 reviews)

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Self-guided cycling

5 nights,
hotel-to-hotel

Level: 2
Moderate

Navigation App

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France : The Loire

Cycling The UNESCO Loire Valley - Deluxe

£1199


4.3 (3 reviews)

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Self-guided cycling

5 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Navigation App

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France : Canal du Midi

Canal du midi Cycling : from Toulouse to Sete

£1219


4.7 (3 reviews)

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Self-guided cycling

6 nights,
hotel-to-hotel

Level: 2
Moderate

Navigation App

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France : Burgundy

Cycling the Vineyards From Beaune to Macon

£1229


4.8 (5 reviews)

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Self-guided cycling

6 nights,
hotel-to-hotel

Level: 1
Leisurely

Printed route
directions

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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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France : The Loire

Cycling The Chateaux Of The Loire - Upgraded Short

£1239


4.7 (3 reviews)

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Self-guided cycling

5 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Navigation App

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Germany : Bavaria

Meandering the Moselle Cycle Path

£1249

NEW FOR 2025

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1
Leisurely

Navigation App

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France : The Loire

Cycling The Chateaux Of The Loire

£1269


4.5 (10 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Navigation App

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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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France : Canal du Midi

Tour de France - Canal du Midi

£1289

NEW FOR 2025

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Self-guided cycling

4 nights,
hotel-to-hotel

Level: 3
Stretching

Navigation App

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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
Navigation App

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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
Navigation App

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France : Atlantic Coast

Tour de France - Atlantic Coast

£1399

NEW FOR 2025

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Self-guided cycling

5 nights,
hotel-to-hotel

Level: 2 & 2+

Navigation App

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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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Italy : Emilia Romagna

Emilia Romagna – Bologna to Parma Cycling

£1439


4.7 (3 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Navigation App

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Italy : Sardinia

Undiscovered Sardinia Cycling

£1459


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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France : The Loire

Cycling The Chateaux Of The Loire - Upgraded

£1619


4.8 (4 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Navigation App

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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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France : Corsica

Corsica with Ebike

£1689


4.5 (2 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2 & 2+

Printed route
directions

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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
Navigation App

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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
Navigation App

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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
Navigation App

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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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South Africa

Cycling the Cape & Winelands

£2699

 
 

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Guided group cycling

11 nights,
hotel-to-hotel

Level: 3
Stretching

Printed route
directions

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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
Navigation App

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France : The Loire

Multi Activity in the Loire

£959

 
 

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Multi-activity holiday

5 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Navigation App

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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
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.