Despite not visiting for 50 years, this island is still my favourite place

Mark Chipperfield

February 19, 2026 — 5:00am

Big Daddy drove us to the pink sand beach in his spotless Vauxhall saloon. After gliding under some welcome shade, he popped the trunk to reveal a large, well-stocked bar. He beamed like a magician who has just sawn his female assistant in half.

My 12-year-old brain went into freefall – if Big Daddy, a mere hotel doorman, lived in such epic style what sort of luxuries were wealthy Bermudians currently enjoying?

In the 1970s Bermuda, a far-flung British possession in the North Atlantic, was a playground for America’s super rich who came to waterski, frolic by the pool and drink endless Manhattans. The local bobbies wore British style helmets and long Bermuda shorts. The island, just 40 kilometres in length, was dotted with brightly coloured limestone cottages. The few cars on the island observed a 35km/h speed limit.

From the 1930s onwards Bermuda attracted a steady stream of celebrities, such as Gary Cooper, Princess Margaret and Telly Savalas, becoming as fashionable as Monaco, Antibes and Capri.

Many actors, businessmen and sports stars bought holiday houses on the island. “You can go to heaven if you want to. I’d rather stay here in Bermuda,” wrote Mark Twain, a frequent visitor to the island.

The Chipperfield family did not belong to the jet set. My father owned a small dairy farm in south Devon – none of us had ever stepped into a Boeing 707 before and our idea of abroad was a daytrip to Calais.

So how did we end up mixing with Bermuda’s gilded class?

The answer was my grandfather James (Jim) Chipperfield who had landed a job at The Castle Harbour Hotel, Bermuda’s most exclusive five-star property which boasted five swimming pools, a ballroom and several restaurants; horse-drawn carriages took guests to a nearby beach.

Built in the era of steamship travel, the hotel reeked of money and class. For a few magical days it was our private playground.

As the grandchildren of Jim Chipperfield, the man who ran the hotel’s furnishings department, we were treated with great kindness by the local Bermudian staff. We explored every corridor, swam in the pools, took carriage rides and posed for snaps with Big Daddy.

Apart from the Castle Harbour’s size and opulence, what struck me most about the hotel was its strong sense of community, knitting together people from all corners of the globe. Life on Bermuda seemed to consist of an endless round of beach picnics, long lunches and cocktail parties.

Grandad Jim, always a convivial man, hosted parties in his company cottage just down the road from the hotel. There was jazz on the record player and a good supply of rum punch. The men wore linen suits and the women summer dresses. My mother had a beehive.

For a child who knew little beyond farm life, these gatherings were impossibly exotic, like something from a movie starring Sidney Poitier. Our holiday in Bermuda had a profound impact on our family, broadening our horizons certainly but also leaving a kernel of dissatisfaction about our life on the farm. My own trajectory as a journalist certainly began on that island – as did my life-long love of great hotels that might, but never quite do, match the sumptuousness of the Castle Harbour.

Before Bermuda grandad Jim was working as a night watchman in London. Having sold his upholstery business, his career was effectively over. He became an object of pity. Then he spotted an ad in the paper for someone with his skills to work in Bermuda, applied and got the job. The next few years were the happiest of his entire life.

From my grandad I learned about the power of optimism, strong male friendships (Big Daddy and Jim were inseparable) and the importance of dressing well even if you’re skint.

“A gentleman always travels with a light suit, a tennis racket, and a spare ticket for the theatre,” wrote the dramatist Terence Rattigan and I think my grandad lived by a similar code. Jim continued to travel into his ’80s. He died in a hotel bar in Spain, having just polished off a double whisky.

My memories of Bermuda are inseparably linked to grandad Jim who embraced island life with gusto. Bermuda also provided my first real exposure to American culture. Hamilton, the capital, had a pre-war drug store that served burgers and milkshakes; nothing quite prepares you for that first taste of real American burger.

Everything here was different from our homeland. Avocados, loquats, cherries, bananas and paw paw grew in abundance on the island. No-one owned an overcoat and the air was scented and balmy.

It’s been five decades since I visited Bermuda, a place which provided some of my fondest childhood memories and a glimpse into a lost world of luxury, privilege and style. It will always be my happy place.

At 17 Mark Chipperfield was a deckhand on a freighter sailing from Auckland to Rotterdam. He has since worked as a news reporter, foreign correspondent and​​ travel writer. Mark lives in Sydney with his wife and 10-year-old son.