If you’re the kind of traveller who’d pick a windswept cliff path over a shopping street any day, then Portland is your dream island.
This isn’t a postcard-pretty, palm-tree-strewn tourist trap. Portland is raw. It’s real. It’s rugged as hell. And it’s absolutely packed with offbeat places, eerie stories, military ruins, secret coves, and trails where you won’t see another soul.
We take people here every day — and they never expect it to be this cool.
So here it is: your ultimate guide to what to do on the Isle of Portland… if you’re into wild walks, salty stories, and the kind of coastal views that make your jaw drop.
Let’s start with the big one.
The South West Coast Path snakes all the way around Portland, and it is absolutely epic. Think high cliffs, sea stacks, secret coves, and views that make you stop mid-step. You’ll pass everything from World War-era pillboxes to strange stone sculptures hidden in old quarries.
Pick it up from East Weares, just behind the prison walls, and follow the trail around the island to Portland Bill. You’ll get blowholes, crashing waves, and maybe even dolphins if you’re lucky.
Top tip: do it in winter. The wind will try to kill you, the sea will try to pull you in — but you’ll feel very alive.
The scenery was stunning, and our guide captivated us with intriguing tales about the region’s past—truly a memorable experience!
This place is surreal — like an open-air art gallery collided with a derelict moonscape.
Tout Quarry is an old stone quarry turned sculpture park, where artists have carved directly into the Portland stone. Some pieces are weird, some are wonderful, some you’ll only spot if you go looking for them. The quarry is overgrown, atmospheric, and slightly eerie in the best possible way.
You might find carvings of dolphins, giant faces, abstract shapes, or just sit in the silence and let the history soak in.
Most people never find this — even locals forget it’s here.
Built in the 1890s to defend the harbour from enemy ships, the Verne High Angle Battery is a hidden network of gun pits and tunnels carved into solid rock. It looks like something from a post-apocalyptic film set — moss-covered, rusting, silent.
Bring a torch. Seriously. And expect echoes.
Above Church Ope Cove, tucked behind ancient stone walls, lies the graveyard of St Andrew’s Church. It’s quiet now — moss-covered tombstones, broken steps, trees growing through the old gate — but it’s full of stories.
Many of the gravestones are carved with skull and crossbones, a symbol not just of death, but of piracy. Portlanders were known for a bit of wrecking and smuggling back in the day, and this place feels haunted. Especially on a grey day.
Watch your step on the way down. The path is steep, the history is deep.
Bet you didn’t expect Portland to be one of the UK’s best dive spots, did you?
The waters off the coast are full of shipwrecks, reefs, and marine life. Whether you’re a beginner or an experienced diver, there are loads of options here — from shore dives at Chesil Cove to boat dives on deeper wrecks out near the harbour wall.
Expect crabs, cuttlefish, conger eels, and maybe a few surprises.
Never dived before? Try a taster session. The local dive shops are ace, and the underwater world here is as wild as the cliffs above it.
Legend says there’s a black barge that glides silently through Portland Harbour on foggy nights — no sails, no crew, no sound. Those who see it are said to die within a week.
It’s one of those tales people here won’t laugh off. There are even old navy logs and lighthouse reports that mention it. Ghost ship or local pub myth? Who cares — it makes for a brilliant story.
Walk along the east side of the island toward the breakwater at dusk, and keep an eye on the horizon. If you see it… maybe don’t tell anyone.
A combo not to be missed.
First, you’ve got Rufus Castle — crumbling walls, ivy-covered battlements, and a commanding view over the sea. Named after William Rufus (the red-haired son of William the Conqueror), it’s one of those places that feels older than time.
Then, just below it: Church Ope Cove, a sheltered shingle beach that used to be a landing point for smugglers. It’s not easy to get to, and that’s the point. Come for a wild swim, a quiet moment, or just to stare at the crashing waves.
It’s the kind of spot that makes you feel like you’re in a novel.
Chesil Beach isn’t a soft sand stroll. It’s hard going. The shingle shifts underfoot, the wind always blows straight into your face, and you’ll find yourself shouting just to be heard.
But it’s worth it.
Walk it in the golden hour for some of the best light you’ll ever see. Look for fossils, driftwood, or just walk until the sound of civilisation disappears. Just don’t try it in flip-flops. You’ll regret it instantly.
We’ve said it before, but it’s worth repeating: The Cove House Inn is the place to end your day. Especially if it’s cold, windy, or you’ve been hiking all afternoon.
Pint in hand, storm lashing the windows, fire crackling behind you — this is the real Portland experience. The kind that makes your bones tired and your soul happy.
Fancy’s Farm – Randomly placed petting farm with killer views.
The Old Engine Shed Café – Tucked near the prison, good cake and stronger coffee.
The Portland Museum – Surprisingly interesting, full of stone lore and smugglers’ tales.
Mermaid Trail – Folk art hidden in plain sight along the esplanade, if you know where to look.
Portland isn’t polished. It doesn’t have glossy brochures or Instagram filters slapped on every corner. What it does have is depth. Edge. Stories. Secrets. And a wild beauty that stays with you.
So lace up your boots, bring your sense of adventure, and go get a little lost.
You’ll be glad you did.
We run small group tours to all these places and more. Want to really get under Portland’s skin?
Book a Tour With Us