Wine Tasting Cycling Holidays

Showing 62 out of 333 trips

For all our wine tasting cycling holidays we place huge importance on the pleasure you can gain from sampling local wines. Our routes take you through the finest vineyards and give you pleny of opportunities to sample the local wines - and our reps will collect any purchases you make and take them to your hotel for free.

Click on the appropriate 'View Holiday' button for full holiday details, take a look at our activities section for further information about how our cycling holidays work, or see our memorable meals page for further information about the fine food and wine you can expect on your wine tasting cycling holiday.

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Italy : Puglia

Cycling the Heel of Italy - Alberobello to Lecce

£1049


4.7 (44 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

£1119


4.6 (8 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

£1189

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

£1229


5.0 (2 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
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Italy : Trentino

Brenner Pass to Venice Cycling

£1469


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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Portugal : Mainland Portugal

Cycling in the Douro Valley

£1519

 
 

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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

£1629


4.7 (14 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

£1839

NEW FOR 2025

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Navigation App

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Portugal : Mainland Portugal

Coimbra to Lisbon Cycling

£1989

NEW FOR 2025

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Self-guided cycling

11 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
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Norway

Cycling in the Lofoten Islands

£3839


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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Italy : Veneto

Heart of Veneto Cycling

£1069


4.8 (73 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

£1119


4.7 (20 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Navigation App

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Italy : Tuscany

A Taste of Tuscany Cycling

£1319


4.9 (28 reviews)

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Self-guided cycling

7 nights,
single centre

Level: 2+
Moderate plus

Headwater
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Italy

Venetian Villas and Vineyards Cycling

£1319


4.7 (57 reviews)

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Self-guided cycling

8 nights,
hotel-to-hotel

Level: 1
Leisurely

Headwater
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France : Provence

Cotes du Ventoux Cycling

£1389


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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Portugal : The Algarve

Cycling in The Real Algarve

£1419


4.7 (66 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

£1589


4.5 (22 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

£2229


4.8 (123 reviews)

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Self-guided cycling

10 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
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France : The Dordogne

Dordogne Valleys & Villages Cycling

£1169


4.7 (45 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

£1469


4.6 (125 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
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Austria : Lake Constance

Lake Constance Cycling

£1489


4.7 (91 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

£1549


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

£1579


4.7 (86 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

£2039


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

£839


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

£879

 
 

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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

£949

NEW FOR 2025

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Self-guided cycling

3 nights,
hotel-to-hotel

Level: 3
Stretching

Navigation App

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France : Burgundy

Classic Burgundy Cycling

£1009


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

£1029


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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France : The Loire

Multi Activity in the Loire

£1059


5.0 (1 reviews)

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Multi-activity holiday

5 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Navigation App

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France : Provence

Hilltop Villages of Provence Cycling - Short Break

£1069


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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France : The Loire

Cycling The Chateaux Of The Loire - Short Break

£1069


4.7 (7 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

£1069


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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Italy : Veneto

Adriatic Coast - Venice to Porec Ride

£1099

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 : Alsace

Cycling the Wine Route of Alsace

£1129


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 : Champagne

Cycle The Wine Route of Champagne

£1149

 
 

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Self-guided cycling

5 nights,
twin centre

Level: 2+ & 3

Navigation App

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France : Burgundy

Cycling The Grand Crus of Burgundy

£1249


5.0 (1 reviews)

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Self-guided cycling

6 nights,
twin centre

Level: 1+
Leisurely plus

Printed route
directions

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France : The Loire

Tour de France - Loire

£1279

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

£1289


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

£1299


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 : Provence

Hilltop Villages of Provence Cycling

£1309


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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France : Canal du Midi

Canal du midi Cycling : from Toulouse to Sete

£1319


4.8 (5 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

£1329


4.8 (6 reviews)

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Self-guided cycling

6 nights,
hotel-to-hotel

Level: 1
Leisurely

Printed route
directions

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France : The Loire

Cycling The Chateaux Of The Loire - Upgraded Short

£1339


4.8 (4 reviews)

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Self-guided cycling

5 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Navigation App

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Germany : The Moselle

Meandering the Moselle Cycle Path

£1349

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

£1369


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

£1379


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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France : Canal du Midi

Tour de France - Canal du Midi

£1389

NEW FOR 2025

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Self-guided cycling

4 nights,
hotel-to-hotel

Level: 3
Stretching

Navigation App

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France : The Dordogne

Dordogne Activities

£1389


4.8 (32 reviews)

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Multi-activity holiday

8 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
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Italy : Tuscany

Cycling the hills of San Gimignano by E-bike

£1459

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 : Atlantic Coast

Tour de France - Atlantic Coast

£1499

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

£1529


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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Italy : Sardinia

Undiscovered Sardinia Cycling

£1549


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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Italy : Emilia Romagna

Emilia Romagna: Bologna to Parma Cycling

£1579


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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France : The Loire

Cycling The Chateaux Of The Loire - Upgraded

£1719


4.7 (7 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Navigation App

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Italy : Piedmont

Cycling the Wine Villages of Piedmont by e-bike

£1729


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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France : Corsica

Corsica with Ebike

£1819


4.7 (3 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

£1829


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

£1849


4.9 (13 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 : Italian Lakes

Cycling the Italian Lakes

£1859


4.8 (5 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

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Italy

Highlights of Puglia Cycling

£2059


4.8 (13 reviews)

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Self-guided cycling

10 nights,
hotel-to-hotel

Level: 1+
Leisurely 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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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.