The Story Behind Long Story, Plettenberg Bay
Every great story begins somewhere and for Long Story, it began with a cupboard.
For years, owner Chereen and her family had spent their holidays in Plettenberg Bay, soaking up the easy rhythm of coastal life at their family home. Chereen has always had an eye for beauty and a soft spot for pieces that tell a story – especially old furniture with character and soul.
On one of those holidays, she wandered into a local shop, Old & New Plett, and spotted a cupboard that instantly caught her heart. It was elegant, full of history, and exactly her style – but the timing wasn’t right. She left without it, but the image lingered.
Years later, her father – now living in Plett – called with news that the same cupboard was still there and now marked down. Without hesitation, Chereen said yes, asking him to buy it on the spot.
But then came the question – what to do with it?
She called husband, Wayne, who owns a well-known trucking company, to ask whether he could get it to Johannesburg. His reply was half suggestion, half spark of fate – “Why don’t we find somewhere to put it in Plett instead?”
And that was it – the idea that changed everything.
Plans were cancelled, they travelled to Plett, and the very first house they viewed would go on to become Long Story Guesthouse. It wasn’t perfect – yet – but Chereen saw what it could be.
Through thoughtful renovation and design, she and her family transformed it into a warm, soulful retreat where every detail has meaning. From carefully chosen furniture (some old, some new) to personal touches that make guests feel instantly at home, the space reflects her love for stories – the ones found in people, in places, and sometimes, in the most unexpected beginnings.
Long Story is more than a name.
It’s a journey – one that started with a cupboard and grew into a guesthouse filled with heart, heritage, and hospitality.
Every space at Long Story has its own quiet charm – a blend of thoughtful design, personal detail, and the kind of warmth that makes you instantly feel at home. Whether it’s coffee on the patio, an afternoon nap by the pool, or a quiet time in the garden, it’s a place where moments slow down and memories begin to take shape.
Come stay where stories begin – and perhaps add a new chapter of your own.
