Look ahead to a host of spectacular new holidays in 2026, as our teams have been working behind the scenes to introduce new handcrafted itineraries.
Our brand-new walking holiday on the Italian Lakes is already proving popular with the Headwater community as you stay on the stunning Lakes Maggiore & Orta, exploring medieval villages, vineyards, and of course sampling the unbeatable local cuisine!
If you're more comfortable on two wheels, our new E-Bike Across Southern Albania trip journeys from mountains to coast across this lesser-discovered country, described by National Geographic as 'Europe's Rising Star'.
Our new holidays continue to offer you a fresh perspective on some of our most-loved Headwater destinations, allowing you time to focus on uncovering hidden gems, sampling the delicious local cuisine and creating those magical moments while we take care of the rest.
Walk the glorious island of Gozo, explore the mighty Triglav National Park in Slovenia's Julian Alps, or meander the idyllic coastline of Fuerteventura.
Hop on your bike and cycle from Coimbra to Lisbon, traverse the Adriatic Coast from Venice to Porec, or meander along the designated Moselle Cycle Path.
If you fancy taking to the water, we have exceptional multi-activity holidays which feature a mix of walking, cycling and kayaking or canoeing; a unique way to discover a new destination.
Canoe the peaceful French waters of the Loire River, hike, bike & paddle Croatia's National Parks, or venture further afield to discover the Sunshine Coast of Canada where lush rainforest, protected inlets, and waterfront retreats await.
Self-guided walking
3 nights,
single centre
Level: 1+ & 2
Headwater
Navigation App
15% OFF THIS TRIP
VIEW TRIP
Self-guided walking
3 nights,
single centre
Level: 1+ & 2
Headwater
Navigation App
15% OFF THIS TRIP
VIEW TRIP
Self-guided walking
4 nights,
single centre
Level: 1+ & 2
Headwater
Navigation App
20% OFF THIS TRIP
VIEW TRIP
Self-guided walking
7 nights,
single centre
Level: 2+ & 3
Headwater
Navigation App
20% OFF THIS TRIP
VIEW TRIP
Self-guided walking
6 nights,
hotel-to-hotel
Level: 3
Stretching
Printed route
directions
10% OFF THIS TRIP
VIEW TRIP
Self-guided walking
7 nights,
hotel-to-hotel
Level: 2+
Moderate plus
Printed route
directions
15% OFF THIS TRIP
VIEW TRIP
Self-guided walking
9 nights,
hotel-to-hotel
Level: 2
Moderate
Headwater
Navigation App
15% OFF THIS TRIP
VIEW TRIP
Self-guided walking
7 nights,
hotel-to-hotel
Level: 2+
Moderate plus
Headwater
Navigation App
20% OFF THIS TRIP
VIEW TRIP
Self-guided cycling
6 nights,
hotel-to-hotel
Level: 2+
Moderate plus
Headwater
Navigation App
15% OFF THIS TRIP
VIEW TRIP
Self-guided cycling
6 nights,
hotel-to-hotel
Level: 1+
Leisurely plus
Navigation App
Self-guided cycling
7 nights,
hotel-to-hotel
Level: 2+
Moderate plus
Navigation App
15% OFF THIS TRIP
VIEW TRIP
Self-guided cycling
7 nights,
hotel-to-hotel
Level: 2+
Moderate plus
Headwater
Navigation App
15% OFF THIS TRIP
VIEW TRIP
Self-guided pilgrimage
5 nights,
hotel-to-hotel
Level: 2+
Moderate plus
Printed route
directions
5% OFF THIS TRIP
VIEW TRIP
Self-guided pilgrimage
6 nights,
hotel-to-hotel
Level: 2+
Moderate plus
Printed route
directions
5% OFF THIS TRIP
VIEW TRIP
Self-guided pilgrimage
6 nights,
hotel-to-hotel
Level: 2+
Moderate plus
Printed route
directions
5% OFF THIS TRIP
VIEW TRIP
Self-guided pilgrimage
7 nights,
hotel-to-hotel
Level: 2
Moderate
Printed route
directions
5% OFF THIS TRIP
VIEW TRIP
Self-guided pilgrimage
7 nights,
hotel-to-hotel
Level: 2+
Moderate plus
Printed route
directions
5% OFF THIS TRIP
VIEW TRIP
Self-guided pilgrimage
7 nights,
hotel-to-hotel
Level: 2
Moderate
Printed route
directions
5% OFF THIS TRIP
VIEW TRIP
Self-guided pilgrimage
7 nights,
hotel-to-hotel
Level: 2+
Moderate plus
Printed route
directions
5% OFF THIS TRIP
VIEW TRIP
Self-guided pilgrimage
8 nights,
hotel-to-hotel
Level: 2
Moderate
Printed route
directions
5% OFF THIS TRIP
VIEW TRIP
Self-guided pilgrimage
9 nights,
hotel-to-hotel
Level: 2+
Moderate plus
Printed route
directions
5% OFF THIS TRIP
VIEW TRIP
Self-guided walking
7 nights,
twin centre
Level: 2
Moderate
Headwater
Navigation App
15% OFF THIS TRIP
VIEW TRIP
Self-guided pilgrimage
9 nights,
hotel-to-hotel
Level: 2+
Moderate plus
Printed route
directions
5% OFF THIS TRIP
VIEW TRIP
Self-guided pilgrimage
9 nights,
hotel-to-hotel
Level: 2
Moderate
Printed route
directions
5% OFF THIS TRIP
VIEW TRIP
Self-guided pilgrimage
10 nights,
hotel-to-hotel
Level: 2+
Moderate plus
Printed route
directions
5% OFF THIS TRIP
VIEW TRIP
Self-guided pilgrimage
11 nights,
hotel-to-hotel
Level: 2
Moderate
Printed route
directions
5% OFF THIS TRIP
VIEW TRIP
Self-guided pilgrimage
13 nights,
hotel-to-hotel
Level: 2+
Moderate plus
Printed route
directions
5% OFF THIS TRIP
VIEW TRIP
Self-guided walking
7 nights,
twin centre
Level: 1+
Leisurely plus
Headwater
Navigation App
15% OFF THIS TRIP
VIEW TRIP
Self-guided cycling
7 nights,
hotel-to-hotel
Level: 1+
Leisurely plus
Navigation App
15% OFF THIS TRIP
VIEW TRIP
Self-guided pilgrimage
4 nights,
hotel-to-hotel
Level: 2+
Moderate plus
Printed route
directions
5% OFF THIS TRIP
VIEW TRIP
Self-guided pilgrimage
15 nights,
hotel-to-hotel
Level: 3
Stretching
Printed route
directions
5% OFF THIS TRIP
VIEW TRIP
Cultural tour
7 nights,
hotel-to-hotel
7 meals
included
Headwater
Navigation App
10% OFF THIS TRIP
VIEW TRIP
Self-guided pilgrimage
13 nights,
hotel-to-hotel
Level: 2+
Moderate plus
Printed route
directions
5% OFF THIS TRIP
VIEW TRIP
Self-guided pilgrimage
5 nights,
hotel-to-hotel
Level: 3
Stretching
Printed route
directions
5% OFF THIS TRIP
VIEW TRIP
Self-guided cycling
7 nights,
hotel-to-hotel
Level: 1+
Leisurely plus
Printed route
directions
15% OFF THIS TRIP
VIEW TRIP
Self-guided pilgrimage
17 nights,
hotel-to-hotel
Level: 2
Moderate
Printed route
directions
5% OFF THIS TRIP
VIEW TRIP
Self-guided cycling
4 nights,
single centre
Level: 1+
Leisurely plus
Navigation App
15% OFF THIS TRIP
VIEW TRIP
Cultural tour
7 nights,
hotel-to-hotel
7 meals
included
Headwater
Navigation App
10% OFF THIS TRIP
VIEW TRIP
Cultural tour
6 nights,
hotel-to-hotel
6 meals
included
Headwater
Navigation App
10% OFF THIS TRIP
VIEW TRIP
Self-guided pilgrimage
24 nights,
hotel-to-hotel
Level: 2 & 2+
Printed route
directions
5% OFF THIS TRIP
VIEW TRIP
Self-guided pilgrimage
9 nights,
hotel-to-hotel
Level: 3
Stretching
Printed route
directions
5% OFF THIS TRIP
VIEW TRIP
Tap here to filter results
Filter and sort
Holiday type
All
Destination
All
Departure month
All
Activity level
All
Accommodation type
All
Best for
New holidays
Sorted by
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.
