Coast · Easy
Coastal Cliffs Trail
Dramatic sea cliffs, hidden coves and ocean air the whole way.
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★ 4.9
Walker rated
Who we are
A walking company run by people who live on the trails.
Heading South began with one guide, a worn map and a love for the paths most travellers never find. Today we lead small groups and private walks along the south's finest trails — from sea-cliff routes to shepherds' paths winding through the hills.
We keep our groups small, our pace relaxed and our routes honest. Whether you want a gentle morning by the coast or a full day to a hidden summit, we'll walk it with you.
- Certified, local mountain guides
- Small groups (max 8) & private walks
- All levels — from easy to challenging
- Snacks, water & safety gear included
Our trails
Choose your path
A selection of our most-loved routes. Every walk can be run as a small group or shaped into a private tour for you and yours.
Valleys · Moderate
Hidden Valleys
Streams, cork oaks & quiet trails.
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Mountain · Hard
Ridge Summit
Big climb, bigger views.
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Sunrise · Moderate
Dawn Walk
Catch the south waking up.
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Villages · Easy
Villages & Vineyards
Whitewashed villages, old cobbles and a tasting stop along the way.
View walk →Why walk with us
Every step in good hands
Local expert guides
Certified guides born and raised in the south. They know the routes, the wildlife and the best spot for lunch.
Small groups
Never more than eight walkers, so the pace stays comfortable and the experience stays personal.
All levels welcome
From gentle coastal strolls to demanding summits — tell us your level and we'll match the trail.
Everything included
Pick-up, water, local snacks, trekking poles and full safety gear. You just bring good shoes.
How it works
Three steps to the trail
1 · Tell us your plans
Send us your dates, group size and the kind of walk you're after. No detail too small.
2 · We craft your walk
We match you to the perfect trail and guide, and reply within 24 hours with a plan and a quote.
3 · Lace up & go
We pick you up, handle the gear and the logistics. You simply enjoy the south on foot.
“The best way to know the south isn't to see it — it's to walk it.”
Walkers' words
Loved by the people we've walked with
★★★★★
The coastal walk was the highlight of our trip. Our guide knew every hidden cove and kept the whole group smiling. Unforgettable.
★★★★★
I'm not a serious hiker, but they matched me with the perfect trail. Felt safe, relaxed and completely looked after the whole day.
★★★★★
We did the summit walk as a family and the guides were brilliant with the kids. Stunning views and a day we'll never forget.
Good to know
Frequently asked questions
Do I need to be fit or experienced?
Not at all. We grade every walk from easy to challenging, so there's a trail for everyone — from a gentle coastal stroll to a full-day summit. Just tell us your level and we'll match you.
What should I bring?
Comfortable walking shoes, a hat and sunscreen, and a light layer. We provide water, local snacks, trekking poles and all safety gear.
Are the walks suitable for children?
Many are. Our easy and moderate trails are family-friendly, and our guides are great with kids. Let us know their ages and we'll suggest the best route.
What happens if the weather is bad?
Safety comes first. If conditions aren't right we'll reschedule, swap to a sheltered route, or offer a full refund — your choice.
Are groups shared or private?
Both. Join a small group of up to eight walkers, or book a fully private walk for just your party. Private walks can be tailored entirely to you.
How do I book?
Send us a request through the form below with your dates and group, and we'll come back within 24 hours with a plan and a quote. No payment until it's confirmed.
Self-guided
Take the trails in your pocket
Prefer to wander on your own? Our free trail app guides you along every route with live GPS, points of interest and offline maps — no signal needed once you're out there.
Open the trail app
Works on any phone · installable · free
Book a walk
Ready to hit the trail?
Tell us when you're around and what kind of walk you fancy — we'll reply within 24 hours with the perfect route and a quote.
- Emailhello@headingsouth.com
- Phone / WhatsApp+351 934 849 924
- Walks departDaily · sunrise to sunset