Headwater are the leading specialists in self-guided holidays since 1985. Each itinerary allows you to travel from place to place at your own pace and showcases the best regional highlights, historical sights, gastronomic cuisine and culture.

Play Video

In 1985, Richard and Christine Bass turned their passion into a business from their kitchen table. With over 35 years of creating expertly crafted routes, Headwater has expanded its collection to include over 200 exhilarating walking, cycling, mixed-activity and snow trips. Designed to take you to the heart of each destination, our holidays create unforgettable moments with the people you love.

Why Travel with Headwater?

Not only do we guarantee expertly crafted routes, characterful accommodations, fantastic local cuisine experiences and excellent customer service, but we also ensure that our sustainable holidays give back more to nature than they take.

Ask an advisor

Speak to a Silver Travel Advisor for advice on where to go, what to do and how to choose your perfect holiday.

Alternatively you can contact our travel partner directly.

01606 822 745


Key Destinations

Albania, Austria, Belgium, Bermuda, Croatia, Cyprus, Egypt, Estonia, Finland, France, Germany, Gozo, Greece, Holland, Iceland, Ireland, Italy, Malta, Montenegro, Morocco, Nepal, Norway, Peru, Portugal, Romania, Slovenia, South Africa, Spain, Sri Lanka, Switzerland, Thailand, Vietnam, UK


Travel from place to place at your own pace. Take the lead with your comprehensive route directions and decide whether you want to linger longer in places of interest – the choice is yours.


Our guided walking holidays are perfect for people who want an escorted walking tour in a small group of like-minded people. Enjoy learning from our local guides and share a moment with some new friends.

Walking Holidays

From gentle coastal walks in Madeira to more challenging treks among the jagged limestone peaks in the Italian Dolomites, our walking routes are as varied and beautiful as the landscapes you’ll encounter.

Cycling Holidays

With our comprehensive route directions, Headwater Navigation App and detailed maps, our relaxing cycling holidays offer great scope for independent exploring, while covering more distance.


On a selection of our trips, you can enjoy a mix of activities that enhance your holiday experience, from walking, cycling and canoeing on the French Dordogne to skiing and snowshoeing in Norway.

Snow Holidays

Enjoy gentle activities like snowshoeing or try your hand at cross-country skiing, dog sledding, horse-drawn sleigh rides and tobogganing in spectacular winter landscapes.

Family Holidays

With family activity trips in Austria, France and Spain, rest assured our itineraries will keep your kids entertained, from canoeing on the Dordogne to taking refreshing dips in Austrian lakes.

Special Offers

Save £100

Enjoy £100 off your next trip by using our discount code SILVERTRAVEL22 at time of booking.

For more details on this offer, please call 0800 412 5678 or

We regularly receive special offers and discounts from our travel partners.

For the latest offers and a bespoke quotation, speak to our Silver Travel Advisors on 0800 412 5678.

Ask an advisor

Speak to a Silver Travel Advisor for advice on where to go, what to do and how to choose your perfect holiday.

Alternatively you can contact our travel partner directly.

01606 822 745

Most recent Reviews


Hotel Ta’ Cenc & Spa

I won a week’s stay half board with Headwater Travel in the November prize draw. The hotel is on the edge of the village




Awesome Austria with Headwater

I actually won this holiday on Silver Travel Advisor last year but as I wasn’t too well then, they kindly let us take it


Featured Articles

For more inspirational content, visit our community for articles, podcasts and advice from our team of travel writers

Come feel the love on a Princess cruise. You’ll enjoy the MedallionClass experience others simply can’t, and it’s exclusively for everyone. Visit incredible destinations and be involved in the best experiences around each one of them.

Experience more with Princess and connect effortlessly with the world around you, spend time away with loved ones, take a moment for yourself, and fall in love with your holiday of a lifetime, every time.

With over 20 years of experience, Wendy Wu Tours has mastered the art of creating exceptional, fully inclusive tours which showcase the very best of each destination.

Each tour is led by a world-class guide, who will highlight the very best of their homeland, and includes authentic cultural experiences so you are not just seeing the sights, but truly immersing yourself in local life.

Say hello to ease at sea. Ambassador’s purpose is simple: they want to inspire every guest to experience authentic cruising, effortlessly and sustainably. Passionate about protecting our oceans and destinations, their ships comply with the highest industry emission standards and there is no single-use plastic on board.

On your voyage, you will receive the warmest of welcomes from the Ambassador community as you sail upon the friendliest ships afloat.

This is a global co-operative co-owned by local partners using real local experts and guides, which supports local communities, environments and wildlife. It offers travellers quirky places to stay, activity holidays and learning experiences. Not In The Guidebooks gets travellers off the beaten track into local culture with day experiences and longer, immersive adventures.

From wild wellness breaks in Wales to painting in Portugal, sustainable adventures in Mauritius to food safaris in Brazil, this is immersive, exciting travel.

Seabourn’s five intimate ships carry guests to the heart of great cities, exclusive yacht harbours and secluded coves around the world, while two new purpose-built expedition ships will combine exhilarating adventures in remote destinations with the sophisticated amenities of the world’s finest resorts at sea.

From the luxury of all suite accommodations to complimentary fine wines and spirits, and a no tipping policy, Seabourn exemplifies the definition of travelling well.