To ensure you taste the best of what a region has to offer, we hand-pick hotels and restaurants whose menus epitomise the local cuisine, taking you truly behind the scenes.

If you're looking to indulge, why not choose to enjoy the culinary delights of the Bistrot or gastronomical restaurant in the Gevrey Chambertin on our Burgundy Walking trip, to sample their unforgettable culinary delights. Or take your holiday experience to another level by tucking into delicious meals during the Loire Gastronomic Cycling trip, where your dinner is prepared by artisan chefs and professional sommeliers at Villa D'Amelia's Michelin-Starred restaurant Damiano Nigro.

Should you wish to take cooking into your own hands, our Walking the Dolomites of Alta Badia holiday offers a chocolate-making experience, a cheese room evening and a wine and liqueur tasting on the hotel terrace that boasts a panoramic backdrop of the Dolomites.

As avid food-lovers ourselves, we know how important local culinary experiences are to our customers, which is every trip itinerary is carefully curated to guide you towards the best cosy British pubs, sizzling tapas restaurants and romantic candle-lit dinners.

If you want your food to be the prominent experience on your trip, we also have gastronomical experiences that offer intimate wine tastings, artisan 3-course meals and more. No matter where you chose to travel with Headwater, we ensure your food always takes you to the very heart of your region's local culture.

Tap here to filter results
 

Austria : The Tyrol

Walking the Kitzbuhel Alps Trail

£1009

NEW FOR 2025

VIEW TRIP

Self-guided walking

6 nights,
hotel-to-hotel

Level: 3
Stretching

Printed route
directions

Spain : The Canary Islands

Contrasts of Lanzarote

£1039


5.0 (4 reviews)

VIEW TRIP

Self-guided walking

7 nights,
single centre

Level: 2
Moderate

Headwater
Navigation App

Italy : Puglia

Cycling the Heel of Italy - Alberobello to Lecce

£1049


4.7 (44 reviews)

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

Spain : The Canary Islands

Contrasts of La Gomera

£1049


4.2 (5 reviews)

VIEW TRIP

Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

Portugal : Madeira

Walking the Waterways and villages of Madeira

£1059


4.2 (6 reviews)

VIEW TRIP

Self-guided walking

7 nights,
single centre

Level: 2+
Moderate plus

Headwater
Navigation App

Spain : The Canary Islands

Walking on Gran Canaria

£1089


5.0 (7 reviews)

VIEW TRIP

Self-guided walking

7 nights,
twin centre

Level: 2
Moderate

Headwater
Navigation App

Italy : Puglia

Cycling the Heel of Italy - Matera to Lecce

£1629


4.7 (14 reviews)

VIEW TRIP

Self-guided cycling

11 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

France : Atlantic Coast

Cycling along the Atlantic Coast

£1839

NEW FOR 2025

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Navigation App

France : Corsica

North Corsican Wonders Between Coast and Mountains

£1289


4.0 (3 reviews)

VIEW TRIP

Self-guided walking

7 nights,
hotel-to-hotel

Level: 2 & 2+

Printed route
directions

Italy : Veneto

Heart of Veneto Cycling

£1069


4.8 (73 reviews)

VIEW TRIP

Self-guided cycling

7 nights,
single centre

Level: 1
Leisurely

Headwater
Navigation App

Italy : Veneto

Walking in the Venetian Hills

£1089


4.7 (90 reviews)

VIEW TRIP

Self-guided walking

8 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

Italy : Tuscany

A Taste of Tuscany Walking

£1269


4.9 (31 reviews)

VIEW TRIP

Self-guided walking

7 nights,
single centre

Level: 2
Moderate

Headwater
Navigation App

Italy : Tuscany

A Taste of Tuscany Cycling

£1319


4.9 (28 reviews)

VIEW TRIP

Self-guided cycling

7 nights,
single centre

Level: 2+
Moderate plus

Headwater
Navigation App

Italy : The Dolomites

Walks in The Italian Dolomites

£1369


4.9 (127 reviews)

VIEW TRIP

Self-guided walking

7 nights,
single centre

Level: 2+
Moderate plus

Headwater
Navigation App

Italy : The Dolomites

Walking the Dolomites of Alta Badia

£1579


4.8 (23 reviews)

VIEW TRIP

Self-guided walking

7 nights,
single centre

Level: 2+
Moderate plus

Headwater
Navigation App

Italy : Sicily

Cycling through Baroque Sicily

£1589


4.5 (22 reviews)

VIEW TRIP

Self-guided cycling

8 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

Italy : Puglia

Contrasts of Puglia Cycling

£1469


4.6 (125 reviews)

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

Croatia

Coastal Croatia - Porec to Pula Cycling

£1579


4.7 (86 reviews)

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

Italy : Piedmont

Gastronomic Barolo Walk

£1809


4.9 (95 reviews)

VIEW TRIP

Self-guided walking

8 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

Italy : Piedmont

Gastronomic Barolo Cycling by e-bike

£2039


4.8 (88 reviews)

VIEW TRIP

Self-guided cycling

8 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
Navigation App

Cyprus

Walking the Akamas Peninsula

£759


4.5 (11 reviews)

VIEW TRIP

Self-guided walking

7 nights,
twin centre

Level: 1 & 2

Headwater
Navigation App

Italy : Veneto

Walking in the Prosecco Hills

£779

NEW FOR 2025

VIEW TRIP

Self-guided walking

5 nights,
hotel-to-hotel

Level: 1+ & 2

Navigation App

Italy : Tuscany

Treasures of Tuscany Walk: San Gimignano to Volterra

£819

NEW FOR 2025

VIEW TRIP

Self-guided walking

7 nights,
twin centre

Level: 2+
Moderate plus

Headwater
Navigation App

France : Champagne

Cycling the Vineyards of Champagne

£879

 
 

VIEW TRIP

Self-guided cycling

3 nights,
single centre

Level: 2
Moderate

Navigation App

France : Alsace

Villages & Vineyards of Alsace- Short Break

£939


5.0 (2 reviews)

VIEW TRIP

Self-guided walking

4 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

France : Provence

Tour de France - Provence

£949

NEW FOR 2025

VIEW TRIP

Self-guided cycling

3 nights,
hotel-to-hotel

Level: 3
Stretching

Navigation App

Italy : Istria

Walking the Highlights of Istria: Italy, Slovenia & Croatia

£999

NEW FOR 2025

VIEW TRIP

Self-guided walking

6 nights,
hotel-to-hotel

Level: 2
Moderate

Navigation App

France : The Loire

Multi Activity in the Loire

£1059


5.0 (1 reviews)

VIEW TRIP

Multi-activity holiday

5 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Navigation App

France : The Loire

Cycling The Chateaux Of The Loire - Short Break

£1069


4.7 (7 reviews)

VIEW TRIP

Self-guided cycling

5 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Navigation App

France : The Loire

Cycling The UNESCO Loire Valley

£1069


5.0 (3 reviews)

VIEW TRIP

Self-guided cycling

5 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Navigation App

Italy : Sardinia

Walking Sardinia's Green Coast

£1079

NEW FOR 2025

VIEW TRIP

Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

France : Alsace

Cycling the Wine Route of Alsace

£1129


4.8 (9 reviews)

VIEW TRIP

Self-guided cycling

5 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Navigation App

Greece : Peloponnese

Peloponnese Coast and Mountain Walking

£1209

NEW FOR 2025

VIEW TRIP

Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

France : The Loire

Tour de France - Loire

£1279

NEW FOR 2025

VIEW TRIP

Self-guided cycling

5 nights,
hotel-to-hotel

Level: 3
Stretching

Navigation App

France : Bordeaux

Cycling The Grand Crus of Bordeaux

£1289


4.5 (4 reviews)

VIEW TRIP

Self-guided cycling

5 nights,
hotel-to-hotel

Level: 2
Moderate

Navigation App

France : The Loire

Cycling The UNESCO Loire Valley - Deluxe

£1299


4.3 (3 reviews)

VIEW TRIP

Self-guided cycling

5 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Navigation App

France : The Loire

Canoeing on the Loire

£1329

 
 

VIEW TRIP

5 nights,
hotel-to-hotel

Navigation App



France : The Loire

Cycling The Chateaux Of The Loire - Upgraded Short

£1339


4.8 (4 reviews)

VIEW TRIP

Self-guided cycling

5 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Navigation App

France : The Loire

Cycling The Chateaux Of The Loire

£1369


4.5 (10 reviews)

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Navigation App

Spain : Rioja

Vineyards of La Rioja Cycling

£1379


4.6 (7 reviews)

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

France : Alsace

Villages & Vineyards of Alsace

£1379


4.4 (7 reviews)

VIEW TRIP

Self-guided walking

6 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

France : Canal du Midi

Tour de France - Canal du Midi

£1389

NEW FOR 2025

VIEW TRIP

Self-guided cycling

4 nights,
hotel-to-hotel

Level: 3
Stretching

Navigation App

Italy : Tuscany

Cycling the hills of San Gimignano by E-bike

£1459

NEW FOR 2025

VIEW TRIP

Self-guided cycling

7 nights,
single centre

Level: 2+ & 3

Headwater
Navigation App

France : Atlantic Coast

Tour de France - Atlantic Coast

£1499

NEW FOR 2025

VIEW TRIP

Self-guided cycling

5 nights,
hotel-to-hotel

Level: 2 & 2+

Navigation App

Italy : Piedmont

Walking the Wine Villages of Piedmont

£1499


4.5 (4 reviews)

VIEW TRIP

Self-guided walking

8 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

Italy : Sardinia

Undiscovered Sardinia Cycling

£1549


4.7 (19 reviews)

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Navigation App

Italy : Emilia Romagna

Emilia Romagna: Bologna to Parma Cycling

£1579


4.7 (3 reviews)

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Navigation App

Italy : Sicily

Sicily: Vino & Volcanoes

£1609


5.0 (2 reviews)

VIEW TRIP

Self-guided cultural tour

7 nights,
hotel-to-hotel

Headwater
Navigation App

Greece : Crete

Walking the Wonders of Crete

£1609

NEW FOR 2025

VIEW TRIP

Self-guided walking

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

France : The Loire

Cycling The Chateaux Of The Loire - Upgraded

£1719


4.7 (7 reviews)

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Navigation App

Italy : Piedmont

Cycling the Wine Villages of Piedmont by e-bike

£1729


4.8 (5 reviews)

VIEW TRIP

Self-guided cycling

8 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
Navigation App

Italy

Highlights of Puglia Cycling

£2059


4.8 (13 reviews)

VIEW TRIP

Self-guided cycling

10 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

Italy : Puglia

Walking in Puglia & Matera

£1499


4.3 (12 reviews)

VIEW TRIP

Guided group walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Printed route
directions

Italy : The Dolomites

Snowshoeing in the Dolomites - Premium Adventure

£1699

 
 

VIEW TRIP

Winter snow holiday

7 nights,
single centre

Printed route
directions

Operated by
Exodus Travels

Italy : The Dolomites

Classic Dolomites - Premium

£2099


5.0 (1 reviews)

VIEW TRIP

Guided group walking

7 nights,
single centre

Level: 3
Stretching

Printed route
directions

Portugal : Mainland Portugal

Portugal: Walking & Wine - Premium Adventure

£2399


4.5 (2 reviews)

VIEW TRIP

Guided group walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Printed route
directions

Tap here to filter results

Filter and sort

Holiday type
All

  • Self-guided walking
  • Self-guided cycling
  • Ski holidays
  • Canoeing
  • Multi activity
  • Pilgrimage
  • Private guided walking
  • Cultural tour
  • Guided group walking
  • Guided group cycling

Destination
All

  • Italy
  • Spain
  • France
  • Portugal
  • UK
  • Albania
  • Andorra
  • Austria
  • Belgium
  • Bermuda
  • Bosnia
  • Canada
  • Cape Verde
  • China
  • Costa Rica
  • Croatia
  • Cyprus
  • Czechia
  • Denmark
  • Egypt
  • Estonia
  • Finland
  • Faroe Islands
  • Germany
  • Greece
  • Holland
  • Iceland
  • Ireland
  • Japan
  • Kenya
  • Malta
  • Montenegro
  • Morocco
  • Nepal
  • Norway
  • Peru
  • Romania
  • Slovakia
  • Slovenia
  • South Africa
  • Sri Lanka
  • Sweden
  • Switzerland
  • Thailand
  • USA
  • Vietnam

Departure month
All

  • Jan
  • Feb
  • Mar
  • Apr
  • May
  • Jun
  • Jul
  • Aug
  • Sep
  • Oct
  • Nov
  • Dec

Activity level
All


  • Leisurely

  • Moderate

  • Demanding

  • Challenging

Accommodation type
All


  • Single centre

  • Twin centre  

  • Hotel-to-hotel

Best for
Food lovers, Wine lovers, Vegetarians

  • Singles
  • Couples
  • Families
  • Food lovers
  • Wine lovers
  • Nature lovers
  • Bird watchers
  • Historic sites
  • Vegetarians
  • Swimming opportunities
  • Electric bikes
  • Tandem bikes
  • GPS navigation
  • Dog friendly
  • Coastal routes
  • Island exploring
  • Lakes and rivers
  • High peaks
  • Unique accommodation
  • Parador hotels
  • New holidays
  • Bestsellers

Sorted by


  • Price

  • Duration

  • Level

Update filters

 

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.

Back to top