In 1985, Richard and Christine Bass made the life-changing decision to turn a passion into a business and thus Headwater was born at their kitchen table. Our first tours were launched in summer 1986 and modestly comprised three holidays in the Upper Loire Valley in France: a canoeing holiday and two self-guided walking holidays. Our vision for Headwater was clear, right from the start. Richard and Christine wanted to offer their customers exactly what they loved in a holiday – family-run, friendly hotels, an authentic experience of a region, including culture, cuisine and fine wines, and above all a fantastic level of personal service, with staff on hand in resort to help and guide as required. After a successful 10 years specialising in France, we launched a new Great Walks in Europe brochure in 1995, offering a selection of hand-picked guided walking holidays in eight countries. As a result of the phenomenal success of this, a year later the first self-guided walking and cycling holidays in Italy were launched. In 1999, Richard and Christine decided to retire and enjoy the fruits of their labour, and sold Headwater – but not before ensuring it was in the safest of hands to continue their legacy. Today, we enjoy taking customers (new and loyal) on journeys on foot or by bike throughout 18 countries worldwide. Whilst we have embraced modern technology and changing times since 1985, Richard and Christine’s ethos remains key to all of our holidays, and we consider it our mission to ensure that the same detail, knowledge and passion goes into delivering each and every trip. With more than 32 years’ experience, our collection now includes 59 self-guided and 12 guided walking holidays and 62 cycling holidays. Our canoeing holiday in the Dordogne remains as popular as ever, as well as our choice of winter snow holidays (cross-country skiing and winter walking) that run between December and April in Austria and Norway. We are particularly proud of our Headwater-employed representatives (reps) who are on-hand in 15 regions in France, Italy, Spain, Portugal, Austria and Bavaria. Burgundy is our longest-standing “repped region” – Richard and Christine researched the holidays and we have been running them since 1992. Our reps provide 24-hour support in resort including: briefing you on arrival, transporting your luggage from hotel to hotel, offering a ‘Wine Service’ where they collect any bottles you’ve purchased en route and transport them to your final hotel for you, and giving you tips and advice and sharing their knowledge of the local area, the routes, the best views and generally helping you to make the most of your trip. Each year, before the season starts, our reps have an in-depth training session at Headwater HQ to make sure they’re ready for the summer ahead. Our newest addition to the Headwater portfolio is a selection of single-centre activity holidays in Brittany and the Dordogne, France and Catalunya, Spain. These are ideal for multi-generational families and groups – take a look for some Headwater inspiration.

Reasons to tour with Headwater

Expert knowledge

Authentic experiences

Expert knowledge

7 Nights $2579 inc flight
7 Nights $1531 inc flight
7 Nights $1524 inc flight
7 Nights $1849 inc flight
7 Nights $2579 inc flight
7 Nights $2319 inc flight
8 Nights $2501 inc flight
6 Nights $1445 inc flight
8 Nights $2149
7 Nights $2410
7 Nights $1667 inc flight
7 Nights $2436 inc flight
Show More