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Wine Tasting Cycling Holidays

Showing 62 out of 329 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 (42 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

£250 SAVING - T&CS APPLY

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Italy : The Dolomites

Cycling from the Dolomites to Venice

£1119


4.7 (7 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Navigation App

£250 SAVING - T&CS APPLY

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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

£250 SAVING - T&CS APPLY

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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
Navigation App

£250 SAVING - T&CS APPLY

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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

£250 SAVING - T&CS APPLY

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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
Navigation App

£250 SAVING - T&CS APPLY

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Italy : Puglia

Cycling the Heel of Italy - Matera to Lecce

£1629


4.7 (13 reviews)

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Self-guided cycling

11 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

£250 SAVING - T&CS APPLY

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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

£250 SAVING - T&CS APPLY

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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
Navigation App

£250 SAVING - T&CS APPLY

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Norway

Cycling in the Lofoten Islands

£3629


5.0 (2 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Navigation App

#250 SAVING - T&CS APPLY

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Italy : Veneto

Heart of Veneto Cycling

£1079


4.8 (73 reviews)

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Self-guided cycling

7 nights,
single centre

Level: 1
Leisurely

Headwater
Navigation App

£250 SAVING - T&CS APPLY

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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

£250 SAVING - T&CS APPLY

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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
Navigation App

£250 SAVING - T&CS APPLY

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Italy : Veneto

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
Navigation App

£250 SAVING - T&CS APPLY

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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
Navigation App

£250 SAVING - T&CS APPLY

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Portugal : The Algarve

Cycling in The Real Algarve

£1419


4.7 (65 reviews)

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Self-guided cycling

6 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

£250 SAVING - T&CS APPLY

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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
Navigation App

#250 SAVING - T&CS APPLY

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Slovenia

Julian Alps to the Adriatic Cycling

£2229


4.8 (121 reviews)

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Self-guided cycling

10 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

£250 SAVING - T&CS APPLY

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France : The Dordogne

Dordogne Valleys & Villages Cycling

£1169


4.7 (44 reviews)

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Self-guided cycling

8 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

£250 SAVING - T&CS APPLY

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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
Navigation App

£250 SAVING - T&CS APPLY

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Austria : Lake Constance

Lake Constance Cycling

£1489


4.7 (90 reviews)

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Self-guided cycling

10 nights,
hotel-to-hotel

Level: 1
Leisurely

Headwater
Navigation App

£250 SAVING - T&CS APPLY

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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
Navigation App

£250 SAVING - T&CS APPLY

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Croatia

Coastal Croatia - Porec to Pula Cycling

£1579


4.7 (85 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

#250 SAVING - T&CS APPLY

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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
Navigation App

£250 SAVING - T&CS APPLY

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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

£250 SAVING - T&CS APPLY

VIEW TRIP

France : Champagne

Cycling the Vineyards of Champagne

£879

 
 

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Self-guided cycling

3 nights,
single centre

Level: 2
Moderate

Navigation App

£250 SAVING - T&CS APPLY

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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

£250 SAVING - T&CS APPLY

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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

£250 SAVING - T&CS APPLY

VIEW TRIP

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

£250 SAVING - T&CS APPLY

VIEW TRIP

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

£250 SAVING - T&CS APPLY

VIEW TRIP

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
Navigation App

£250 SAVING - T&CS APPLY

VIEW TRIP

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

£250 SAVING - T&CS APPLY

VIEW TRIP

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

£250 SAVING - T&CS APPLY

VIEW TRIP

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

#250 SAVING - T&CS APPLY

VIEW TRIP

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

£250 SAVING - T&CS APPLY

VIEW TRIP

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

£250 SAVING - T&CS APPLY

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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

£250 SAVING - T&CS APPLY

VIEW TRIP

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

£250 SAVING - T&CS APPLY

VIEW TRIP

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

£250 SAVING - T&CS APPLY

VIEW TRIP

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

£250 SAVING - T&CS APPLY

VIEW TRIP

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

£250 SAVING - T&CS APPLY

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France : Canal du Midi

Canal du midi Cycling : from Toulouse to Sete

£1319


4.7 (3 reviews)

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Self-guided cycling

6 nights,
hotel-to-hotel

Level: 2
Moderate

Navigation App

£250 SAVING - T&CS APPLY

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France : Burgundy

Cycling the Vineyards From Beaune to Macon

£1329


4.8 (5 reviews)

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Self-guided cycling

6 nights,
hotel-to-hotel

Level: 1
Leisurely

Printed route
directions

£250 SAVING - T&CS APPLY

VIEW TRIP

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

£250 SAVING - T&CS APPLY

VIEW TRIP

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

Optional
e-bike hire

£250 SAVING - T&CS APPLY

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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

£250 SAVING - T&CS APPLY

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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

£250 SAVING - T&CS APPLY

VIEW TRIP

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

£250 SAVING - T&CS APPLY

VIEW TRIP

France : The Dordogne

Dordogne Activities

£1389


4.8 (31 reviews)

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Multi-activity holiday

8 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

£250 SAVING - T&CS APPLY

VIEW TRIP

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

£250 SAVING - T&CS APPLY

VIEW TRIP

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

£250 SAVING - T&CS APPLY

VIEW TRIP

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

£250 SAVING - T&CS APPLY

VIEW TRIP

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

#250 SAVING - T&CS APPLY

VIEW TRIP

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

£250 SAVING - T&CS APPLY

VIEW TRIP

France : The Loire

Cycling The Chateaux Of The Loire - Upgraded

£1719


4.8 (5 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Navigation App

£250 SAVING - T&CS APPLY

VIEW TRIP

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

£250 SAVING - T&CS APPLY

VIEW TRIP

France : Corsica

Corsica with Ebike

£1789


4.7 (3 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2 & 2+

Printed route
directions

£250 SAVING - T&CS APPLY

VIEW TRIP

Slovenia

Secrets of Slovenia Cycling

£1799


4.9 (12 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
Navigation App

£250 SAVING - T&CS APPLY

VIEW TRIP

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

£250 SAVING - T&CS APPLY

VIEW TRIP

Italy : Italian Lakes

Cycling the Italian Lakes

£1859


4.5 (2 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

£250 SAVING - T&CS APPLY

VIEW TRIP

Italy : Puglia

Highlights of Puglia Cycling

£2059


4.8 (12 reviews)

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Self-guided cycling

10 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

£250 SAVING - T&CS APPLY

VIEW TRIP

South Africa

Cycling the Cape & Winelands

£2439

 
 

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Guided group cycling

11 nights,
hotel-to-hotel

Level: 3
Stretching

Printed route
directions

£250 SAVING - T&CS APPLY

VIEW TRIP
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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.