I was unsure what to wear for my first big night out alone in Bermuda. My destination was the Hamilton Princess, a harbourside hotel that, on Friday nights, attracts a lively mix of locals and expats with its happy hour and DJ sets.

The “Pink Palace”, as it is known, is also something of a cultural destination: the corridors are crammed with museum-quality modern art: Damien Hirst, Andy Warhol, Kaws and Banksy.

After a cocktail at 1609 Restaurant, overlooking the party, any lingering solo-traveller anxiety evaporated. Surrounded by a mix of European, American and Bermudian accents, I didn’t feel out of place with the groups of women, men in shiny shoes, youngsters and office workers, even joining in with two tipsy Britons gossiping in the toilets.

I had always wanted to visit Bermuda for its pink beaches, but had been put off by its reputation as a destination for older couples. Between January and June this year, only 11.4 per cent of visitors by air were solo, according to the Bermuda Tourism Authority.

However, I decided not to let that put me off and finally decided to take the plunge, booking for October, when nights in the UK were drawing in and I could return with a smug autumn tan. My only issue with being alone would be applying sunscreen to my back.

Hamilton, Bermuda’s capital, has the slightly surreal prettiness of a toy town. Low-rise offices frame a harbour full of bobbing yachts, the historic Cabinet Building looks like an elaborate dollhouse, and at weekends the financial district empties so completely that you can almost hear the shutters coming down. But it’s not stuffy.

There is a storied relationship with rum stretching back to 1806, when Englishman James Gosling arrived in St George’s with £10,000 worth of spirits, and decades later began blending the molasses-heavy rum that would become Gosling’s Black Seal.

But nightlife here doesn’t mean stumbling out of a club at 2am – it is more about enjoying rum swizzles and dark and stormy cocktails in one of the many pubs (the island’s tavern culture is rooted in its British colonial history). At The Hog Penny, a British-style pub that is a staple of the local live music scene, I spent an enjoyable evening tapping my toes to rock and pop covers.

Then there is the food. Some of Bermuda’s most memorable meals are not the grand hotel dinners alongside honeymooning couples, but roadside joints where the food comes wrapped in paper, the tables are casual and the clientele is overwhelmingly local. I found myself alongside couples, singles and groups of friends, all happy to chat.

Getting around as a solo traveller is fairly straightforward – there are buses, and taxis are plentiful. Although quite pricey, they can be booked easily via the Hitch app. On one journey, I asked my driver, Zita, to pull over for a picture of Bailey’s Bay, and ended up ordering a box of oozing mac’n’cheese at Jamaican Grill. This family-run place has been serving Caribbean classics for more than a decade and was buzzing with tradesmen grabbing lunch on the go for $16 (£12).

On Zita’s recommendation I also tried Mamma Mia, a laid-back spot in Hamilton Parish, with bench seating and a grass-eating goat in the backyard. I went for a local favourite, the Bermudian fish sandwich: breaded and fried wahoo, piled on to a slab of raisin bread with tartar sauce and coleslaw.

While waiting, I sat in the sun outside the adjoining Working Men’s Club, where I sipped a rum cocktail alongside the regulars.

It was the beaches that had drawn me to Bermuda in the first place, so I was eager to see the pink sands of Horseshoe Bay. I became so preoccupied enjoying the crystalline water that I didn’t notice my patch of beach being swallowed up by an influx of cruise tourists.

I shouldn’t have been surprised – the island received more than 467,000 cruise passenger arrivals last year. But lingering longer offers the opportunity to scratch beneath the surface.

Making friends in Bermuda requires almost no effort. After a pub lunch at the Frog & Onion, which has been in business since 1992, I got chatting to a pair of sailors, who casually invited me aboard their catamaran for afternoon drinks.

Another day, I took an e-bike tour with guide Kristin White, who ended up showing me her gorgeous bookshop, Long Story Short, and making a raft of recommendations for my reading list.

At Tobacco Bay Beach Club in historic St George’s, I met charismatic owner Dennie O’Connor, dressed in impeccable white Bermuda shorts, blindingly white knee socks and silver-tipped shoes. The tiny crescent bay is a popular snorkelling spot, and the beach club has masks to hire, but I chose instead to stop at the bar for a cocktail made with Dennie’s own Bermuda Triangle vodka.

As sociable as this island is, when I wanted to be alone, Bermuda would just let me be. I could sit on an empty stretch of sand, swim in the turquoise water or wander down quiet residential lanes without saying a word to anyone. I may have come on my own, but I was never lonely – I felt right at home.

How to do

British Airways flies from Heathrow to Bermuda.

Coco Reef Resort has doubles from £239.

More information: gotobermuda.com