Enjoy a delightful stay at Castell d'Emporda on our Catalan Classic Walk. Perched between the Pyrenees and the Costa Brava's cliffs, This superbly restored 700-year old castle is nestled between ancient olive trees and also holds Europe's largest scale model of the Battle of Waterloo.

Admire the architecture on our Self-Guided Walking in Puglia and Matera, where you’ll stay at Hotel Sassi overlooking the ancient honeycomb structures in Matera's Sassi district.

We’ve been carefully researching and sourcing the finest, friendliest and most charming hotels and characterful accommodations since 1985. Looking out for small, family-owned accommodations that take a genuine interest in their guests, we also keep an eye out for places whose menus epitomise the local cuisine.

Our accommodations offer much more than just a bed for the night. Many are historic properties, castles and palaces that have previously hosted monarchs, renowned artists and famous authors. All are individually selected, and because we have strong, trusted relationships with our hoteliers, you can expect a warm welcome wherever you go.

It's all in the Detail

Some of the places we feature are way off-the-beaten-track in mountain villages while others are in the heart of the most ornate historic centres. Many reflect the tastes and, at times, quirky styles of their owners, with all sharing a desire to provide "service plus" at every point of your stay.

If you’re looking to stay in a small family-run hotel, our Taste of Tuscany Walking trip allows you to stay at Agriturismo La Pietriccia, run by brothers Stefano and Simone near Chianciano, Italy. For a restored castle stay, our Contrasts of Catalonia Cycling takes you to the enchanting Castell d’Emporda which houses Europe’s biggest scale model of the Battle of Waterloo. If you’d like to stay in a modern hotel, complete with a wellness centre, our Cycling from Bruges to Brussels trip, takes you to Hotel Hotel Vé, a former fish smokehouse and cigar factory in 1923, located 450 yards away from Grote Markt.

Hotel ratings

Simply expand the day’s itinerary of the individual holiday pages to find out more about your accommodation. If the holiday is a single centre the hotel information will be shown only in Day 1. We clearly mark each accommodation with our own star rating for guidance purposes.

All our accommodation has been inspected and classified by the authorities of the relevant countries. As there is no direct British equivalent of many classifications, the broad expression ‘hotels’ refers to all the different types of accommodation we use, from friendly family-run B&B and country inns to luxury hotels (where is the country’s official hotel rating).

Headwater’s accommodation star ratings are provided to give you guidance on the relative standard of the accommodation you will be staying in. In most occasions this will match the official star rating of the accommodation, however, if we feel it necessary Headwater will adapt a rating to what we believe is fair. This is based on a variety of checks which can include property visits, customer feedback, facilities and location, or if the accommodation does not hold an official rating of its own. These ratings are reviewed regularly to ensure their accuracy and relevance for guidance purposes.

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Our favourite places to stay

Showing 41 out of trips

Listed below are the holidays that match your search criteria, to view any of the holidays shown simply click on the 'View holiday' button. Use the 'Filter and sort' options to refine your results.

Italy : Puglia

Journey through Puglia to Matera

£1009


4.8 (8 reviews)

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Self-guided cultural tour

7 nights,
hotel-to-hotel

Norway

Cycling in the Lofoten Islands

£3469


5.0 (2 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

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Italy : Veneto

Walking in the Venetian Hills

£849


4.7 (88 reviews)

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Self-guided walking

8 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
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Italy : Veneto

Heart of Veneto Cycling

£939


4.8 (72 reviews)

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Self-guided cycling

7 nights,
single centre

Level: 1
Leisurely

Headwater
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Italy : Puglia

Self Guided Walking in Puglia: From Lecce to Matera

£1009


4.7 (49 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 1
Leisurely

Headwater
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Italy : Tuscany

A Taste of Tuscany Walking

£1169


4.9 (28 reviews)

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Self-guided walking

7 nights,
single centre

Level: 2
Moderate

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Italy : Tuscany

A Taste of Tuscany Cycling

£1219


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

£1279


4.7 (61 reviews)

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Self-guided cycling

6 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
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Switzerland : Valais

Walking in Val D'Anniviers

£1549


5.0 (1 reviews)

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Self-guided walking

7 nights,
single centre

Level: 1 to 3

Printed route
directions

France : Provence

Cotes du Ventoux Cycling

£1729


4.8 (36 reviews)

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Self-guided cycling

6 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

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Spain : Catalonia

Catalan Classic Walk

£819


4.7 (78 reviews)

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Self-guided walking

6 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

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France : The Dordogne

Dordogne River Walk

£1099


4.7 (29 reviews)

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Self-guided walking

8 nights,
hotel-to-hotel

Level: 2
Moderate

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Italy : Puglia

Contrasts of Puglia Cycling

£1279


4.6 (123 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
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United Kingdom : The Cotswolds

Best of the Cotswolds Walk

£1579


4.8 (13 reviews)

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Self-guided walking

8 nights,
hotel-to-hotel

Level: 1
Leisurely

Printed route
directions

Italy : Piedmont

Gastronomic Barolo Walk

£1909


4.9 (91 reviews)

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Self-guided walking

8 nights,
hotel-to-hotel

Level: 2
Moderate

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Italy : Tuscany

Treasures of Tuscany Walk: San Gimignano to Volterra

£719

NEW FOR 2025

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Self-guided walking

7 nights,
twin centre

Level: 2+
Moderate plus

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France : The Loire

Cycling In The Royal Loire Valley

£959

 
 

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Self-guided cycling

3 nights,
single centre

Level: 1
Leisurely

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Spain : Balearic Islands

Walking Mallorca trails and traditional Fincas

£1069

NEW FOR 2025

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

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France : Burgundy

Cycling The Grand Crus of Burgundy

£1119


5.0 (1 reviews)

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Self-guided cycling

6 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Printed route
directions

Norway : Gudbrandsdalen

Cross Country Skiing at Rondane National Park

£1179

NEW FOR 2025

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Winter snow holiday

5 nights,
single centre

Spain : Extremadura

Cycling Central Spain in Style

£1389

NEW FOR 2025

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
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Italy : Emilia Romagna

Emilia Romagna – Bologna to Parma Cycling

£1439


4.7 (3 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

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Greece

Walking the Wonders of Crete

£1439

NEW FOR 2025

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
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Italy : Sardinia

Undiscovered Sardinia Cycling

£1459


4.7 (19 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

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France : The Loire

Cycling The Chateaux Of The Loire - Upgraded

£1619


4.8 (4 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

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France : Provence

Provence Velo Vin Voyage

£1669


4.0 (1 reviews)

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Self-guided cultural tour

7 nights,
hotel-to-hotel

Portugal : Mainland Portugal

Porto to Coimbra Cycling

£1729


4.8 (56 reviews)

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Self-guided cycling

9 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
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Slovenia

Secrets of Slovenia Cycling

£1759


4.9 (11 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
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Morocco

Morocco: Mountains, Desert & Coast

£2079

NEW FOR 2025

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Self-guided cultural tour

7 nights,
hotel-to-hotel

Canada

Walking Canada’s Sunshine Coast

£2449


4.7 (3 reviews)

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Self-guided walking

8 nights,
hotel-to-hotel

Level: 1 to 3

Headwater
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Japan

Shikoku Pilgrimage Trail

£3029

 
 

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Self-guided walking

10 nights,
hotel-to-hotel

Level: 3
Stretching

Printed route
directions

USA : Maine

Cycling Maine's Coast & National Park

£3039

 
 

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
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Japan

Walk the Kumano Kodo

£3259


5.0 (3 reviews)

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Self-guided walking

10 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Printed route
directions

Japan

Walk the Nakasendo Trail

£3299

 
 

VIEW TRIP

Self-guided walking

10 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Printed route
directions

Japan

Japan: Hiroshima & Island Hopping

£3399

NEW FOR 2025

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Multi-activity holiday

10 nights,
hotel-to-hotel

Level: 2
Moderate

Printed route
directions

Morocco

Atlas Panorama

£699

 
 

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Guided group walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Printed route
directions

Albania

Highlights of Albania

£1249

 
 

VIEW TRIP

Guided group walking

9 nights,
hotel-to-hotel

Level: 2
Moderate

Printed route
directions

Egypt

Ancient Egypt & Nile Cruise

£1649

 
 

VIEW TRIP

Guided group walking

8 nights,
hotel-to-hotel

Level: 1
Leisurely

Printed route
directions

Peru

The Inca Trail in Comfort

£2599

 
 

VIEW TRIP

Guided group walking

7 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Printed route
directions

Peru

Peru Explorer

£4699

 
 

VIEW TRIP

Guided group walking

19 nights,
hotel-to-hotel

Level: 2
Moderate

Printed route
directions

Kenya

Kenya Photographic Safari with Paul Goldstein - Premium Adventure

£6799

 
 

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Guided group walking

6 nights,
single centre

Level: 3
Stretching

Printed route
directions

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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.

What our customers say

"Excellent relaxing holiday - accommodation was faultless."
Mrs Pitchforth, St Albans

"Fantastic accommodation and wonderful food!"
Mr Dickinson, Truro

"The locations were beautiful and the accommodation characterful and uniformly excellent, as was the food (and drink!) throughout."
Mr Larner, Dublin

"The accommodations and food were amazing and we would not have been able to find them on our own."
Mrs Merricks, USA

"The holiday was about as good as it gets, especially the accommodation and food, which was often provided in nearby restaurants."
Mr McGeoch, Bristol

"All accommodation was very good, with the Hotel Montmirail and Chateau de Mazan being truly excellent."Dr O'Grady, Warrington

"Our accommodation was superb at all three hotels and staff were friendly and knowledgeable."Mrs Reir, Inverurie

"The accommodation was delightful and made the most of the historical features."Dr File, Dundee