Shore leave: Sun, sea and shorts in Bermuda

Pink. Not red, not scarlet or maroon. Certainly not claret. Not even – and here I squeezed my eyes half shut and mentally dimmed the lights a little – mauve. No, the shorts were unambiguously pink. Bruce Robinson, divisional merchandise manager at the English Sports Shop in Hamilton, Bermuda, had picked them out for me especially, due to their popularity with visitors. "South Africans all come here for pink shorts," he said as he handed them over. "They love them."

I'm not South African, and I don't think I share their affinity for pink. But I was prepared to take Robinson's word on pretty much anything to do with Bermuda shorts. After all, he started working at the English Sports Shop 45 years ago when he was 12, so knows more than most about selecting proper island attire.

The British Army started wearing what later became known as Bermuda shorts as part of their military uniform in tropical terrain. The Army didn't wear pink, of course, but our boys wanted to look smart and at the same time keep things nice and airy from the waist down. Bermuda shorts still perform that dual role: pleasantly voluminous, they stop about an inch above the knee and are made from suit material. "But," as Robinson pointed out, "they are actually tapered inwards – it's not just taking a pair of suit trousers and cutting them off."

In Bermuda, such shorts are part of proper business attire, usually accessorised with a short-sleeved shirt, a tie, a blazer and long socks. The accompanying footwear, Robinson informed me as he peered disapprovingly down at my battered sandals, should really be a pair of loafers.

Apparently the colour of your shorts should also complement rather than match your jacket, so the English Sports Shop doesn't sell too many pairs in black or navy. The rest of the spectrum was well-represented, however. Bright blue, or even green, looked good. But Robinson swiftly selected a tie and socks, then sent me – pink shorts in hand – to the changing room, from where I later emerged, a butterfly of mid-Atlantic business chic. The price tag for the whole ensemble was just US$389 (£260) before loafers.

These idiosyncratic garments might be part of the charm of a visit to the island – the local policemen look particularly fetching in them – but they also sum up how Bermuda works. Only 750 miles from Washington, DC, this tiny subtropical speck is where formal English tradition meets the airy pragmatism of the US, which supplies most of its tourist income. So it's entirely appropriate that a pair of tailored shorts has been adopted as the tourist board's logo.

Four hundred years ago this month, an adventurous fellow called Sir George Somers set off from England to relieve the colony of Jamestown in Virginia, which had been settled a couple of years previously. Unfortunately a storm blew up and he wrote off his ship, the Sea Venture, on a reef near Bermuda's shore. Shakespeare is said to have used the incident as the basis for the shipwreck in The Tempest – a character in the play refers to the "still-vexed Bermoothes". Poet Andrew Marvell later satirised the arrival of the puritans who found themselves enjoying Bermuda's "eternal spring, which here enamels everything" instead of the expected hardship of the New World.

Keen to make light of his inconvenience, Sir George claimed the island for the crown, despite it having been discovered 100 years earlier by the Spanish. Bermuda is the oldest remaining British overseas territory, with St George's – the dinky town at the island's north-western tip – the longest continually inhabited English town in the Americas.

Nowadays, this fish-hook shaped patch of land is perhaps best known for being a tax haven with some fine beaches, but its strategic position off America's eastern seaboard has occasionally seen it assume a significance greater than its tiny size (20 square miles all told) would suggest.

During the war between Britain and the US in 1812-15, for example, American ships attacked merchant vessels off Bermuda to much consternation on this side of the Atlantic; when the American Civil War of 1861-65 broke out, the islands became a haven for Confederate shipping; and in the Second World War it served as a base for Allied warships hunting German U-boats.

The day before I arrived, Bermuda found itself in the middle of yet another transatlantic storm, as it welcomed four controversial new settlers fresh from Guantanamo Bay. The US Government's decision to negotiate directly with the Bermudian Premier, Ewart Brown, about accepting the ex-prisoners led to outrage from the UK Foreign Office and predictable concern here on the island.

Half of those I met felt that the pro-independence Brown was pandering to US President Obama in order to sever ties with the UK (a referendum in 1995 strongly rejected that option). The other half felt it was sensible to cosy-up to the US, given the implications of Obama's stated desire to abolish offshore tax-havens. All, however, were united in the feeling that they'd like at least to have been consulted. The local newspaper, The Royal Gazette, reported that a motion of no confidence was being tabled as a result of Brown's "reckless, autocratic and unaccountable" leadership style. (He later survived it comfortably. Our own Premier Brown was probably rather envious.)

Only 65,000 people live in Bermuda – and Hamilton, which lies at the centre of the island, is the only settlement that could loosely be described as a city. It's a pretty place, focused around Front Street, which runs parallel to the harbour. Here visitors can enjoy expensive boutique shopping opportunities and café-bars with ocean views.

I visited during a red-letter weekend: the Tall Ships participating in the 2009 Atlantic Challenge were berthed along the seafront, their rigging festooned with flags. The arrival of these mighty vessels coincided with the Queen's Birthday Parade along Front Street – less spectacular than the Trooping of the Colour, perhaps, but arguably more heartfelt. Members of the Bermuda regiment, the fire brigade and police officers (in uncomfortable-looking trousers rather than shorts) processed solemnly past local dignitaries, to an accompanying fanfare from a brass band.

I was booked into the nearby Rosedon Hotel, a quiet guest house that, along with other period properties near Hamilton, offers a pleasing contrast to the vast US-style resorts elsewhere.

The Rosedon is cosy rather than chic, and its rooms – set out in the blue-shuttered main building and in two separate blocks behind – are charming in a faded, end-of-the-Empire sort of way. Mine had a four-poster bed, a wooden lamp in the shape of an elephant and a huge ceiling fan which, along with some serious air-conditioning, coped nicely with the humid evenings.

Each morning a splendid US-style breakfast was served up by the pool, but the Rosedon balanced this indulgence with a disarming habit of providing complimentary tea and fruitcake each day at 4pm. Now that's how you keep both sides of the Pond happy.

Hamilton itself boasts a handful of impressive buildings: at the eastern end of Church Street is the square-shaped Sessions House, with its tall clock tower, where the repercussions of this month's political turmoil are no doubt still reverberating. Walk a couple of minutes west, past Bermuda's Victorian Cathedral (the completion of which conferred city status on Hamilton) and you arrive at the white-walled City Hall, which also houses the tiny Bermuda National Gallery. Here, a collection of shiny Bermudian motorbikes is currently on show, along with a series of photographs and sketches chronicling the history of the island. In truth, little seems to have changed in the 100-year transition from sepia tones to full-colour digital prints.

Bermuda is, frankly, a conservative sort of place. A sign outside a detached Victorian building on Queen Street commemorates the fact that "from this house the first Bermuda postage stamp was issued in the year 1848 by William B Perot, Postmaster of Hamilton". Stamps are still being issued from the same premises, although a modern post office lurks elsewhere.

Queen Street, incidentally, runs parallel to Washington Street – more evidence of Bermuda's delicate political balancing act.

From Hamilton, Bermuda stretches westwards, curving delicately towards the business end of its fish-hook shape via the Parishes of Paget, Warwick, Southampton and Sandys. In the opposite direction the island splits around the bay of Harrington Sound at the pretty Flatts Village before reaching St George's, known as the "East End" of the island. An efficient network of buses joins everything up, or if you're feeling flush you can take a taxi. Alternatively, you can hire a scooter to get around.

I'd never ridden a scooter before – and there's probably a very sensible argument that says learning to do so on winding foreign roads is an unwise undertaking. Having said that, the maximum speed limit is 35mph, everyone rides or drives on the left, and provided you're careful it's a liberating way of seeing what the island has to offer. After a surprisingly brief overview of my vehicle's functions (basically: this is the accelerator, those are the brakes, here's your helmet) and a redundant explanation – presumably aimed at US tourists – of how roundabouts work, I revved off to Hamilton's ferry terminal.

It costs $4 (£2.60, with the same fare again for a scooter) and takes 25 minutes to make the crossing from Hamilton to Bermuda's major historical landmark: the Royal Naval Dockyard at the island's western extremity. This huge former naval base, crowned by a fort, was constructed to service the British fleet during the 19th century. A Maritime Museum now lies inside, detailing everything from Bermuda's historic role in the slave trade to the hundreds of shipwrecks that throng the offshore reefs – and which now make for excellent diving sites.

There's also the tiny Snorkel Beach, reached through an arch in the fortress, where you can hire snorkel equipment and splash among parrot fish near the sea wall. The reef here isn't spectacular, but the water is wonderfully warm and the naval detritus littering the sea bed – an anchor here, a cannon there – makes for a diverting swim. Elsewhere, vast gun emplacements point out to sea from below the veranda of the Commissioner's House, a reminder of Bermuda's key position on British trade routes . On the day I visited the guns were trained on the Norwegian Spirit, a vast cruise ship on a round-trip from Boston, as it came in to dock. V C Despite the presence of these cruise ships, the island never felt crowded. I scootered eastwards on quiet roads, past a naval graveyard with sobering memorials to those "found drowned", "died of heatstroke" or "died from rupture of a blood vessel", then pressed on through the pretty parish of Sandys.

The island of Bermuda is in fact nothing of the kind, but rather a series of smaller atolls, linked together by causeways and bridges. Somerset Bridge is reputed to be the smallest drawbridge in the world: with a maximum width of just 30 inches, it rises only to allow the masts of sailboats to pass through. After crossing it, I passed more of the brightly painted houses which adorn the island, their stepped white roofs designed to catch the rain.

In Southampton Parish I paused to climb the 185 steps of Gibbs' Hill lighthouse, with its lofty views from Hamilton all the way back to the Dockyard, but even at ground level the views were spectacular. At every turn lay a stretch of green coast, or a tiny offshore island, or a marina – or, of course, a beach.

It's at the South Shore Park where you find the best beaches in Bermuda. And let's face it, this is what you came here for: pink-coral sands, sheltered coves, azure sea. In a stretch of coast not even two miles long, I walked from the broad sweep of Warwick Long Bay and the rocky sanctuary of Jobson's Cove, via tiny Stonehole Bay and onwards to Horseshoe Bay, the only beach on the island that ever seemed to have more than a dozen or so people on it.

OCCASIONALLY Bermuda seems slightly unreal, like a resort that you can never leave. But tourist attractions such as the underwhelming Crystal Caves in Hamilton Parish and the cramped Aquarium and Zoo at Flatts Village only serve to highlight the rich vein of history and natural beauty available elsewhere on the island. The tiny Spittal Pond nature reserve near Flatts is a pretty place with a wild, rocky shore. It also contains what is presumed to be the island's first-ever piece of graffiti: "RP 1548", carved into a rock face. The RP is thought to stand for Rex Portugaliae, an inscription left by marooned Portuguese sailors. In an ironic turn of events, this historic "tag" had to be replaced by a bronze cast after vandalism and weathering destroyed the original.

Resorts can, of course, be spectacular places: golf courses, with their attendant luxury accommodation are found scattered over the island. The scenic route eastwards from Flatts Village winds through two spectacular examples: Tucker's Point and the Mid Ocean Club. Beyond lies some of Bermuda's most expensive real estate, on an island where the cost of living is already sky-high.

Past Tucker's Point, a long, grey strip of causeway connects St David's island to Hamilton Parish. In 2003 this slender artery was severed by a hurricane, isolating St George's Parish from the rest of the island – but the blue skies and lapping water that greeted me could hardly have been more benign.

The town of St George – once the only settlement in Bermuda and now a Unesco World Heritage Site – suffers from being a little too neat and tidy, seemingly designed solely to direct tourists towards its museums and pricey gift shops. But a walking tour of the town soon served up its own lesson in history: the segregated graveyard of St Peter's; the Unfinished Church rising, skeletal, above the town (the parishioners ran out of cash before it could be finished); the gracious State House, where Bermuda's first parliament was held; the narrow alleys and delicate white-washed buildings which preserve a Bermuda long since vanished.

There are forts dotted all over Bermuda's coastline, most constructed in the 19th century, then gradually abandoned between the First and Second World Wars. Now, they're part of Bermuda's network of National Parks. At St Catherine's Fort, just to the north of St George, people were picnicking next to the fort's obsolete cannon as they watched a flotilla of boats pass nearby. It seemed a pragmatic response to the crumbling monument – and an appropriate one too, given Bermuda's modern role as a financial and tourist hub, rather than a military stronghold.

Now, of course, Bermuda is caught once again between the US and British government, albeit in a fashion that requires diplomacy rather than fortress-building. Those one-time Guantanamo detainees might find it strange to have fetched up in a place where the Queen of England's head adorns a currency measured in dollars, but I found it reassuring to discover that trousers are always called trousers in Bermuda, never pants. And shorts, of course, are something Bermuda will always call its own.

Getting there

The writer travelled with Prestige Holidays (01425 480400; prestigeholidays.co.uk), which offers a one-week stay at the Rosedon Hotel from £1,384 per person (based on two people sharing) in September 2009, including midweek return flights from Gatwick with British Airways, accommodation with breakfast in a standard room and private taxi transfers. From October, BA flights will increase from five to six each week.

Staying there

Rosedon Hotel, 61 Pitts Bay Road, Hamilton, Bermuda (00 441 295 1640; rosedon.com).

Getting around

Scooter rental services are widely available. The writer used Smatt's Cycle Livery (00 441 295 1180; smattscyclelivery.com); $50 (£33) per day, $221 (£148) per week.

Eleven bus routes operate on the island, with regular connections. Ferry services operate between Hamilton and the west and east ends. A day travel pass costs $12 (£8), a week costs $45 (£30).

Visiting there

The English Sports Shop, 49 Front Street, Hamilton (00 441 295 2672).

Bermuda Maritime Museum , Royal Naval Dockyard (00 441 234 1418; bmm.bm). Admission $10 (£6.70)

Gibbs' Hill Lighthouse, Southampton Parish (00 441 238 8069; bermudalighthouse.com). Admission $2.50 (£1.70)

Crystal Caves, 8 Crystal Caves Road, Hamilton Parish (00 441 293 0640; caves.bm). Two caves, Crystal and Fantasy, can be visited. Admission $16 (£10.50) per cave; $23 (£15) for a combination ticket

Bermuda Aquarium, Museum and Zoo, 40 North Shore Road, Flatts (00 441 293 2727; bamz.org). Admission $10 (£6.70).

More information

Bermuda Department of Tourism: bermudatourism.com