Wine Tasting Cycling Holidays

Showing 67 out of 338 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.

Italy : Puglia

Cycling the Heel of Italy - Alberobello to Lecce

NZ$2000


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

NZ$2220


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

NZ$2400

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

NZ$2485


5.0 (1 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

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Portugal : Mainland Portugal

Cycling in the Douro Valley

NZ$3125

 
 

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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

NZ$3210


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

NZ$3830

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

NZ$4160

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

NZ$4180


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

NZ$7635


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

NZ$3585


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

NZ$2070


4.8 (72 reviews)

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Self-guided cycling

7 nights,
single centre

Level: 1
Leisurely

Headwater
Navigation App

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Italy : Veneto

Bolzano, Verona & Venice Ride

NZ$2375


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

NZ$2375


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

NZ$2685


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

NZ$2815


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

NZ$3255


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

NZ$3805


4.8 (36 reviews)

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Self-guided cycling

6 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

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Slovenia

Julian Alps to the Adriatic Cycling

NZ$4160


4.8 (118 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

Landscapes of the Luberon Cycling

NZ$4490


4.4 (21 reviews)

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Self-guided cycling

8 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

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France : The Dordogne

Dordogne Valleys & Villages Cycling

NZ$2355


4.7 (42 reviews)

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Self-guided cycling

8 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

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Italy : Puglia

Contrasts of Puglia Cycling

NZ$2815


4.6 (123 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

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Austria : Carinthia

Lake Constance Cycling

NZ$3060


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

NZ$3190


4.4 (59 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1
Leisurely

Headwater
Navigation App

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Croatia

Coastal Croatia - Porec to Pula Cycling

NZ$3255


4.7 (85 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

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Italy : Piedmont

Gastronomic Barolo Cycling by e-bike

NZ$5060


4.8 (88 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 : Burgundy

Cycling in Beaune Vineyards

NZ$1630


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

NZ$1715

 
 

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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

NZ$1870

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

NZ$2000


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

NZ$2045


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

Cycling In The Royal Loire Valley

NZ$2110

 
 

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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

NZ$2110

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

NZ$2135


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

NZ$2135


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

NZ$2265


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

NZ$2465


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

NZ$2510

 
 

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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

NZ$2595

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

NZ$2620


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

NZ$2640


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

NZ$2685


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

NZ$2705


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

NZ$2705


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 : The Loire

Cycling The Chateaux Of The Loire - Upgraded Short

NZ$2730


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

NZ$2750

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

NZ$2795


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

NZ$2815


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

NZ$2840

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

NZ$2990

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

NZ$3035


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

NZ$3080

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

NZ$3145


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 : Emilia Romagna

Emilia Romagna – Bologna to Parma Cycling

NZ$3170


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

NZ$3210


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

NZ$3565


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

NZ$3630


4.0 (1 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

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France : Corsica

Corsica with Ebike

NZ$3720


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

NZ$3805


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

NZ$3870


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

NZ$4115


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

NZ$4445


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

NZ$4840


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

NZ$5940

 
 

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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

NZ$1850


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

NZ$2110

 
 

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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

NZ$2840


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.