Wine tasting walking holidays

Showing 52 out of 329 trips

For all our wine tasting walking 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 plenty of opportunities to sample the local wines. On our self-guided holidays our reps will even 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 walking holidays work, or see our memorable meals page for further information about the fine food and wine you can expect on your wine tasting walking holiday.

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Spain : Asturias

Majestic Mountains of the Picos de Europa

CA$2080


4.8 (8 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Navigation App

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Austria : The Tyrol

Walking the Kitzbühel Alps Trail

CA$2120

NEW FOR 2025

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Self-guided walking

6 nights,
hotel-to-hotel

Level: 3
Stretching

Printed route
directions

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Spain : The Canary Islands

Contrasts of Lanzarote

CA$2175


5.0 (4 reviews)

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Self-guided walking

7 nights,
single centre

Level: 2
Moderate

Headwater
Navigation App

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Spain : The Canary Islands

Contrasts of La Gomera

CA$200


4.2 (5 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

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Portugal

Walking the Waterways and villages of Madeira

CA$2215


4.2 (6 reviews)

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Self-guided walking

7 nights,
single centre

Level: 2+
Moderate plus

Headwater
Navigation App

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Italy : Umbria

Undiscovered Villages of Umbria Walk

CA$2235


4.8 (11 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

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Spain : The Canary Islands

Walking on Gran Canaria

CA$2270


5.0 (7 reviews)

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Self-guided walking

7 nights,
twin centre

Level: 2
Moderate

Headwater
Navigation App

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France : The Loire

Chateaux Of The Loire Walk

CA$2785


4.4 (7 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 1
Leisurely

Navigation App

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France : Corsica

North Corsican Wonders Between Coast and Mountains

CA$2650


4.0 (3 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 2 & 2+

Printed route
directions

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Italy : The Bay of Naples

Paths of the Amalfi Coast

CA$1780


4.6 (28 reviews)

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Self-guided walking

7 nights,
single centre

Level: 2
Moderate

Headwater
Navigation App

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Italy : Veneto

Walking in the Venetian Hills

CA$2270


4.7 (88 reviews)

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Self-guided walking

8 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

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Italy : Tuscany

A Taste of Tuscany Walking

CA$2615


4.9 (28 reviews)

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Self-guided walking

7 nights,
single centre

Level: 2
Moderate

Headwater
Navigation App

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Italy : The Dolomites

Walks in The Italian Dolomites

CA$2785


4.9 (126 reviews)

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Self-guided walking

7 nights,
single centre

Level: 2+
Moderate plus

Headwater
Navigation App

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Portugal : Madeira

Marvels of Madeira Walk

CA$2920


4.7 (124 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

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France : Provence

Landscapes of the Luberon Walk

CA$2995


4.7 (37 reviews)

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Self-guided walking

8 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

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Italy : The Dolomites

Walking the Dolomites of Alta Badia

CA$3205


4.8 (23 reviews)

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Self-guided walking

7 nights,
single centre

Level: 2+
Moderate plus

Headwater
Navigation App

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Portugal : The Algarve

Walk the Algarve's Wild West

CA$2445


4.8 (89 reviews)

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Self-guided walking

6 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

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France : The Dordogne

Dordogne River Walk

CA$2480


4.7 (29 reviews)

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Self-guided walking

8 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

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Italy : Piedmont

Gastronomic Barolo Walk

CA$3640


4.9 (92 reviews)

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Self-guided walking

8 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

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Portugal : Mainland Portugal

Walking the Green Coast of Minho

CA$1320


4.0 (1 reviews)

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Self-guided walking

7 nights,
single centre

Level: 2
Moderate

Printed route
directions

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Cyprus

Walking the Akamas Peninsula

CA$1645


4.5 (11 reviews)

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Self-guided walking

7 nights,
twin centre

Level: 1 & 2

Headwater
Navigation App

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Portugal : Mainland Portugal

Walking the Mountains, Valleys & Coast of Minho

CA$1645


5.0 (1 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Printed route
directions

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Spain : Asturias

Highlights of the Picos de Europa

CA$1760


4.3 (6 reviews)

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Self-guided walking

7 nights,
single centre

Level: 3
Stretching

Headwater
Navigation App

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Italy : Tuscany

Treasures of Tuscany Walk: San Gimignano to Volterra

CA$1760

NEW FOR 2025

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Self-guided walking

7 nights,
twin centre

Level: 2+
Moderate plus

Headwater
Navigation App

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Greece

Walking on Kythnos Island

CA$1780


5.0 (2 reviews)

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Self-guided walking

6 nights,
twin centre

Level: 2+
Moderate plus

Headwater
Navigation App

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Portugal : Madeira

Walk the Garden Island of Madeira

CA$1815


4.8 (4 reviews)

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Self-guided walking

7 nights,
single centre

Level: 2
Moderate

Headwater
Navigation App

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Spain : Catalonia

Catalonia Activities

CA$1835


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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Cyprus

Contrasts of Cyprus Walking

CA$1835


4.6 (7 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 1+ to 2+

Headwater
Navigation App

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Germany : Bavaria

Walking in the Altmuhltal Nature Park

CA$1930


4.0 (1 reviews)

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Self-guided walking

8 nights,
hotel-to-hotel

Level: 2
Moderate

Navigation App

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France : The Loire

Chateaux Of The Loire Walk - Short Break

CA$1950

 
 

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Self-guided walking

4 nights,
hotel-to-hotel

Level: 1
Leisurely

Navigation App

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France : Alsace

Villages & Vineyards of Alsace- Short Break

CA$1985


5.0 (2 reviews)

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Self-guided walking

4 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

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Austria : The Danube

Walking the Wachau Heritage Trail

CA$2065


5.0 (2 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Navigation App

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Italy : Istria

Walking the Highlights of Istria: Italy, Slovenia & Croatia

CA$2100

NEW FOR 2025

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Self-guided walking

6 nights,
hotel-to-hotel

Level: 2
Moderate

Navigation App

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Greece

Walking on Kythnos Island - Premium

CA$2160


4.6 (7 reviews)

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Self-guided walking

6 nights,
twin centre

Level: 2+
Moderate plus

Headwater
Navigation App

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Italy : Sardinia

Walking Sardinia's Green Coast

CA$2160

NEW FOR 2025

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

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France : Burgundy

Walking in Burgundy's Vineyards - Short Break

CA$2175

 
 

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Self-guided walking

4 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

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France : The Loire

Multi Activity in the Loire

CA$2215

 
 

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Multi-activity holiday

5 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Navigation App

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Greece : Peloponnese

Peloponnese Coast and Mountain Walking

CA$2500

NEW FOR 2025

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

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Italy : Tuscany

Wine & Walk in Chianti

CA$2500


4.0 (2 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Printed route
directions

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Italy : Umbria

Walking on the Francigena Way

CA$2520


4.6 (11 reviews)

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Self-guided pilgrimage

9 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
Navigation App

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France : Burgundy

Walking in Burgundy's Vineyards

CA$2635


4.7 (7 reviews)

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Self-guided walking

6 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

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Portugal : Mainland Portugal

Walk the Highlights of Northern Portugal

CA$2805


4.5 (6 reviews)

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Self-guided walking

8 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
Navigation App

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France : Alsace

Villages & Vineyards of Alsace

CA$2825


4.4 (7 reviews)

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Self-guided walking

6 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

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France : The Dordogne

Dordogne Activities

CA$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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Spain : Balearic Islands

Walking Mallorca trails and traditional Fincas

CA$2880

NEW FOR 2025

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Navigation App

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Italy : Piedmont

Walking the Wine Villages of Piedmont

CA$3050


4.5 (4 reviews)

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Self-guided walking

8 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

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Portugal : The Azores

Island Hopping in the Azores

CA$4060


4.3 (3 reviews)

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Self-guided walking

14 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

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Italy : The Bay of Naples

Walking the Amalfi Coast

CA$2565


4.7 (10 reviews)

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Guided group walking

7 nights,
single centre

Level: 2
Moderate

Printed route
directions

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Italy : Puglia

Walking in Puglia & Matera

CA$2660


4.3 (12 reviews)

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Guided group walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Printed route
directions

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Italy : Veneto

Walk The Prosecco Hills & Hidden Venice

CA$2660


4.8 (5 reviews)

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Guided group walking

7 nights,
single centre

Level: 2
Moderate

Printed route
directions

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Italy : The Dolomites

Classic Dolomites - Premium

CA$3135


5.0 (1 reviews)

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Guided group walking

7 nights,
single centre

Level: 3
Stretching

Printed route
directions

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Portugal : Mainland Portugal

Portugal: Walking & Wine - Premium Adventure

CA$4560


4.5 (2 reviews)

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Guided group walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Printed route
directions

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.