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

£989


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

£1009

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

£1039


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

£1049


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

£1059


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

£1069


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

£1089


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

£1359


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

£1289


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

£829


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

£1089


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

£1269


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

£1359


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

£1429


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

£1469


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

£1579


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

£1179


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

£1199


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

£1809


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

£589


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

£759


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

£759


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

£819


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

£819

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

£829


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

£849


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

£859


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

£859


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

£909


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

£919

 
 

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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

£939


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

£979


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

£999

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

£1029


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

£1029

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

£1039

 
 

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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

£1059

 
 

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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

£1209

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

£1209


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

£1219


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

£1279


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

£1369


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

£1379


4.4 (7 reviews)

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Self-guided walking

6 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

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

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Spain : Balearic Islands

Walking Mallorca trails and traditional Fincas

£1409

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

£1499


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

£2029


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

£1349


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

£1399


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

£1399


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

£1649


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

£2399


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.