Ranked and rated: The final pieces of the British Empire
There was a time when, to use the old adage, the sun did not set on the British Empire. It certainly didn’t back in 1920, when this globe-straddling entity reached its territorial apex – a geopolitical behemoth of 13.7 million square miles and 500 million inhabitants; the largest empire the planet has ever seen.
With feet planted firmly in all four hemispheres – from the northern and western extremities of Canada to the portion of Antarctica claimed for the Union flag; from sunny Caribbean islands to the distant shores of New Zealand and Australia – here, indeed, was a realm where daylight was always shining somewhere.
Remarkably, this remains the case. The British footprint can still be found in places as varied as the Pacific and Indian Oceans, the South Atlantic, and the familiar backdrop of the Caribbean. But here in 2024, the terminology is rather different, and the area involved is considerably smaller.
Little more than a century on from its most super-sized hour, the list of this country’s non-domestic satellites now extends to “just” 617,763 square miles of landmass, some 250,000 people, and 14 British Overseas Territories (BOTs) – each of them with an element of self-governance; most of them offering something to the tourist.
Most of them? This article will attempt to rank 11 of the 14 British Overseas Territories in order of their viability as holiday destinations; a line-up that will take into account their accessibility as well as their attractiveness to the visitor.
This means that we can immediately discount three of the 14 – British Antarctic Territory (the claim to which has been suspended since the Antarctic Treaty of international cooperation came into play in 1961), Akrotiri and Dhekelia (twin military bases on Cyprus) and British Indian Ocean Territory (another military enclave, largely revolving around the island of Diego Garcia).
But that leaves a top-ten-plus-one that, depending on your levels of wanderlust, you might wish to explore in part or in full. Where to start? That’s a matter of choice.
There are cold corners and balmy beaches, historical havens and truly remote idylls – but at least one of them is up, awake and going about its daytime business at any given moment.
MAP: https://part.icle.link/zw02h0m
11. Pitcairn Islands
British since:
1838 (first settlement in 1790)
Where are they?
Politely, in the middle of nowhere. The South Pacific is generally seen as a place of wide horizons and empty waters, but the Pitcairn “archipelago” particularly underscores this viewpoint. It says a lot for a place’s remoteness when one of its nearest neighbours is Chile’s statue-laden outpost Easter Island, which sits 1,200 miles to the east.
What are they?
Four islets scattered across a broad space. How scattered? Well, the distance between the westernmost island, Oeno, and the easternmost, Ducie, is 380 miles. Neither of them has any population. Nor does Henderson, the biggest, which makes up 86 per cent of the landmass. Everyone lives on Pitcairn itself. All 47 people – most of whom are descended from the mariners who staged the fabled “Mutiny on the Bounty”, in 1789.
Main reason to go:
You have just commandeered a British merchant vessel, casting its captain adrift in a lifeboat, and are seeking safe refuge in an unknown corner of the ocean. Failing that, you are a restless wanderer – determined to explore the entire planet.
Best bit
Bounty Bay, on the north-east coast of Pitcairn, just beyond the capital Adamstown, where the vague remnants of HMS Bounty lie below the surface – Fletcher Christian and his co-fugitives having scuttled it here to avoid detection, in January 1790.
How to do it
By passenger ship, from Mangareva, in French Polynesia, some 430 miles to the west. The sailing timetable – and all other details – can be found at visitpitcairn.pn.
10. Falkland Islands
British since:
1833 (with prior settlement in 1765)
Where are they?
In the South Atlantic, 300 miles east of Argentina’s Patagonian coast.
What are they?
The most emotive of the British Overseas Territories. The Falklands War of 1982 is only the bitterest example of the long-running animosity between Argentina and Britain over what are two large outcrops (West Falkland and East Falkland), plus 776 islets, strewn across 4,700 square miles of ocean. The South American country has been laying claim to what it terms “Las Malvinas” since the 1830s – when British sovereignty over the archipelago was established. That 10-week conflict 42 years ago saw Buenos Aires state its case with bullets, but made no difference to the islands’ nationality. In a 2013 referendum, Falklanders voted overwhelmingly – 99.8 per cent – to remain British.
Main reasons to go:
A fascination with a dark – but ultimately triumphant – episode in recent British history. Combined, possibly, with an interest in the birdlife – the gentoo, the rockhopper, the Magellanic penguin, the soaring albatross – visible in the archipelago. (Or, simply, you are going to Antarctica anyway, and it makes sense to drop in en route.)
Best bit:
Stanley – on the east edge of East Falkland – is one of the planet’s doughtiest capitals. It is also alive with links to Britain, from the pounding hooves and regular meetings of its racecourse, to the reserved Anglican worship at Christ Church Cathedral.
How to do it:
Rainbow Tours (020 8131 8981; rainbowtours.co.uk) makes good on the promise inherent in its “Falklands in Depth” holiday – a 15-day odyssey which offers a detailed combination of respectful remembrance and days with binoculars glued to eyes and skies. From £4,695 per person – including flights from Chile (but not from the UK).
9. South Georgia and the South Sandwich Islands
British since:
1775 (claimed for Britain by James Cook); 1843 (formal government)
Where are they?
In the shadow of the South Pole. Although 1,380 miles separate South Georgia from the tip of the Antarctic Peninsula, and the Falkland Islands are closer (810 miles to the west), this collection of inhospitable and (largely) uninhabited islands feels very much part of the frozen realm at the bottom of the planet. South Georgia, in particular, echoes the Heroic Age of Antarctic Exploration. Ernest Shackleton’s desperate – but doggedly successful – voyage to it in April 1916, after his Imperial Trans-Antarctic Expedition had become marooned further south, was one of the greatest feats of the time.
What are they?
A twin-set of (very) rugged archipelagos. South Georgia – by far the largest of these islands (1,362 square miles) – is surrounded by nine or so groups of islets (such as the Welcome Islands). The South Sandwich Islands, laid out between 350 and 500 miles south-east of South Georgia, are 11 volcanic outcrops of irredeemable solitude.
Main reasons to go:
You are a 19th-century whaler – or an early 20th-century explorer. Or, you are booked onto an Antarctic cruise that will take you to the islands on the way.
Best bits:
If you are especially enthralled by Antarctic explorers, Shackleton’s grave. He is buried at Grytviken, a former whaling station on the north-east coast of South Georgia – having died there of a heart attack on a subsequent expedition (on January 5 1922). If you are there for the scenery or geography, the Fortuna Glacier is an enormous ice beast.
How to do it:
AE Expeditions (0808 189 2005; aexpeditions.co.uk) will call upon South Georgia (as well as the Falkland Islands) as part of a 23-day “Antarctica Complete” voyage that is currently scheduled to sail in and out of Ushuaia between January 30 and February 21 (2005). Prices from US$33,386 (£26,716) per person (not including flights).
8. Montserrat
British since:
1667 (Treaty of Breda)
Where is it?
Firmly, squarely, in the Caribbean, as one of the Leeward Islands. To be precise, it sits at the bottom corner of an imaginary (and almost equilateral) triangle that links it to Antigua (33 miles to the north-east) and Nevis (38 miles to the north-west). If you climb Nevis Peak, on the latter, you can spot Montserrat shimmering in the distance.
What is it?
In a word, “fiery”. A good number of the main Caribbean islands have volcanic origins, but Montserrat has taken the smoke-and-lava thing to an extreme. In August 1995, Soufriere Hills – the multi-domed stratovolcano which dominates the southern section of the landmass – abandoned a century of dormancy to begin an eruption which lasted, on and off, for four years.
This infernal outpouring devoured the capital Plymouth, turning it into a modern Pompeii, while ongoing volcanic activity rendered W.H. Bramble – the main international airport, out on the east coast – unusable by 2010. The disaster saw Montserrat lose about two thirds of its population (to emigration; some 7,000 people moved away) – and the bottom half of the island is still fenced off as an official exclusion zone, so prone is Soufriere Hills to tantrums. But a fresh airport, John A. Osbourne, has been built in the north. It welcomes flights from across the Caribbean.
Main reason to go:
The recent history may be tricky, but the weather is still glorious.
Best bit:
There are lovely small towns (Little Bay, Davy Hill, Brades) and beaches (Little Bay Beach, Rendezvous Beach) along the north-west flank of the island. Visitors can also get surprisingly close to the main event. The Montserrat Volcano Observatory (mvoms.org) peers at Soufriere Hills from a high vantage point and a safe distance. Montserrat Island Tours goes further, offering a variety of trips into the interior, including a jaunt into the ashen ruins of Plymouth (from US$100/£79; montserratislandtours.com).
How to do it:
A seven-night stay at the Chez Mango Villas in Old Town, checking in on June 22, costs from £912 (in total) – through Expedia (020 3024 8211; expedia.co.uk). Fly Montserrat flies into the island from Antigua (001 664 491 3434; flymontserrat.com).
7. Gibraltar
British since:
1713 (Treaty of Utrecht)
Where is it?
At the southern tip of the Iberian Peninsula, pretty much at the point where the Atlantic meets the Mediterranean via the Strait of Gibraltar. The clue is in the name.
What is it?
Hardy nugget of land, just 2.6 square miles in area – and permanent bone of contention between Spain and Britain. Madrid ceded Gibraltar – a place of significant military and strategic value – to London more than three centuries ago, “in perpetuity”, towards the end of the War of the Spanish Succession (1701-1714), and has complained about the “in perpetuity” part ever since.
Brexit hasn’t helped, thrusting an extra wedge of bureaucracy between “The Rock” and its neighbour – 96 per cent of Gibraltans voted Remain in 2016. But the same Gibraltans rejected the idea of shared British-Spanish sovereignty in another referendum, in 2002, so the clunky status quo seems set to endure.
Main reason to go:
A city break on the Costa del Sol that doesn’t involve being on the Costa del Sol. Gibraltar is surrounded by Andalusia on all sides, but argues that there is more than enough within its territory to keep visitors entertained – from landmarks such as the National Museum (gibmuseum.gi) and the Trafalgar Cemetery (home to some of those who perished in the 1805 battle), to the many bars and restaurants along the marina.
Best bit:
The Rock itself; the distinctive limestone crag which rears to 1,398ft (426m). You can scale it on foot. Or, if you aren’t feeling energetic, by cable car (gibraltarinfo.gi).
How to do it:
A three-night stay at the four-star Elliot Hotel, flying from Bristol on June 6, costs from £613 a head, with easyJet Holidays (0330 493 0787; easyjet.com/holidays).
6. Cayman Islands
British since:
1670 (Treaty of Madrid)
Where are they?
Towards the north-west corner of the Caribbean Sea, roughly midway between Cuba (to the north), Jamaica (to the southeast) and Mexico (directly to the west).
What are they?
A trio of islands – Grand Cayman, Cayman Brac, Little Cayman – that are generally viewed as gleaming hubs of off-shore finance and opaque tax-haven regulations, but also wish to be known as holiday destinations in the Caribbean tradition.
Main reason to go:
See above – sun, sea and sand.
Best bit:
Seven Mile Beach, the aptly monikered strip of sand which adorns the west end of the biggest island, Grand Cayman – just above the archipelago’s capital, George Town.
How to do it:
Seven Mile Beach is festooned with chic bars, high-end restaurants and five-star hotels. A seven-night getaway to one of them, the Westin Grand Cayman Seven Mile Beach Resort, flying in from Heathrow (via the Bahamas) on May 25, costs from £2,894 per person, through British Airways Holidays (0344 493 0787; ba.com.holidays).
5. St Helena, Ascension and Tristan da Cunha
British since:
1657 (St Helena; governance charter for the East India Company)
Where are they?
Collectively, in the South Atlantic. Although “collectively” may not be the most apt word to describe a British Overseas Territory whose northernmost island, Ascension (just a little below the equator, roughly on the same latitude as Recife in north-east Brazil), sits a full 2,253 miles from the most southerly, Gough Island (a remote satellite of Tristan da Cunha, which lies level with central Argentina). Still, three disparate locations are packaged together as one BOT. Do not try to swim between them.
What are they?
Volcanic. St Helena, Ascension and Tristan da Cunha are all born of lava. The former, arguably, is the most celebrated. Not just because of its natural beauty, but because it was once a prison for the planet’s then-most famous inmate. In the wake of his defeat and defenestration at the Battle of Waterloo in June 1815, Napoleon Bonaparte spent the final six years of his life on the island – eventually dying there, on May 5 1821.
Main reason to go:
Because St Helena, in particular, supplies a spectacular sort of remoteness, without being quite as remote as it once was. The opening of an airport, after many various delays, in 2016, finally connected the island to the world beyond the shipping lanes. Prior to the runway’s construction, the main way in was by mail-ship from Cape Town. Now there are flights in from Johannesburg – and on up to Ascension.
Best bit:
If you are fascinated by the biggest story, Longwood House, the mansion where Napoleon spent most of his exile, is now a museum (see sainthelenaisland.info). If all that wild geography is more intriguing, you can hike up to St Helena’s summit, Diana’s Peak (2,684ft/818m), for epic views. The BOT’s highest point – Queen Mary’s Peak on Tristan da Cunha – is much higher (6,765ft/2,062m), but said island can only be reached by boat.
How to do it:
Cazenove + Loyd (020 7384 2332; cazloyd.com) offers a seven-night St Helena getaway from £3,900 a head, including flights in from Johannesburg (though not from the UK). Oceanwide Expeditions (0031 118 410 410; oceanwide-expeditions.com) goes into greater detail with its “Atlantic Odyssey” – a 23-night voyage which sets off from Ushuaia (in Argentina), and visits Gough Island and Tristan de Cunha, as well as St Helena. Next departure March 23-April 15 2025 – from €7,850 per person (flights extra).
4. Anguilla
British since:
1667 (Treaty of Breda)
Where is it?
Squarely within the grand bend of Caribbean outcrops that is the Lesser Antilles – and, specifically, towards the northern tip of the Leeward Islands chain. That splendid Dutch-French collaboration, Sint Maarten/St Martin, lies immediately to the south; the British Virgin Islands and (a bit further on) Puerto Rico are away to the west.
What is it?
A 35-square-mile nugget of coral and limestone with a curiously tetchy history. While part of the British fold, Anguilla has been bounced from pillar to post; fobbed off into government arrangements with, at various times, Antigua, and St Kitts. Particularly frustrated with the latter situation, islanders held a pair of referenda, in 1967 and 1969, seeking to sever ties with their Caribbean cousin. Finally, in 1980, Anguilla became a Crown Colony – the precursor to British Overseas Territories – in its own right.
Main reason to go:
Sunbathing, with the occasional lazy stroll towards the water. Anguilla’s coral DNA makes snorkelling above the reef a wholly rewarding exercise. The Prickley Pear Cays, a short boat ride away to the north-west, are particularly suited to hours in masks and flippers. Viator sells day-trips from Sandy Ground, on the sail-boat Tradition – from £388 per person (020 3318 0421; viator.com; tour reference 43363P3).
Best bit:
Anguilla has some of the planet’s finest beaches. There are more than 30 dotted around the island perimeter, of which Shoal Bay, on the north coast, may be the loveliest.
How to do it:
Turquoise Holidays (01494 678 400; turquoiseholidays.co.uk) offers “Heavenly Antigua & Idyllic Anguilla”; a 10-night escape that splits its time evenly between five-star resorts on the islands. From £5,840 a head – with flights and transfers.
3. Turks and Caicos Islands
British since:
1783 (Treaty of Paris)
Where are they?
If you are being strictly literal, in the western Atlantic Ocean – directly north of Haiti and the Dominican Republic, and due east of Cuba. However, the proximity of these neighbours should be a clue that, if not in precise geography, the Turks and Caicos are effectively Caribbean. They certainly keep to the regional template in everything else – culture, climate, outlook, ambience, food, history, and softness of sand.
What are they?
A pair of island groups, combined into one administrative whole. The “Turks” half of the equation amounts to eight pin-prick outcrops on the east side of the archipelago; the more substantial “Caicos” part of the jigsaw adds up to some 32 pieces, of varying sizes – including the significant triumvirate of North, Middle and East Caicos. As with the Cayman Islands, off-shore finance has long been a lifeblood of the economy – but tourism is increasingly important, and incoming passenger numbers are increasing.
Main reason to go:
Beach relaxation.
Best bit:
Providenciales, the most populated island (in both the Caicos group and the entire archipelago). Here, a necklace of luxury resorts gleams on the glorious north coast. Some Caribbean destinations offer mountain trails and chances for adventure. Snoozing next to warm waters of a stereotypical blue, the Turks and Caicos are all about indolence.
How to do it:
Virgin Atlantic launched a direct flight between Heathrow and Providenciales last November. A seven-night getaway to the five-star Wymara Resort & Villas, flying in on May 16, starts at £3,477 a head (0344 4729646; virginholidays.co.uk).
2. British Virgin Islands
British since:
1672 (captured from the Dutch)
Where are they?
Roughly in the middle of the grand arc of Caribbean islands which begins with Cuba, and curves all the way around to Tobago. More specifically, between close cousins the US Virgin Islands and Puerto Rico (directly to the west) and two rather more distant neighbours – Sint Maarten/St Martin, and fellow BOT Anguilla (to the east).
What are they?
Altogether, 55 or so islets and cays, of which the four biggest are Tortola, Virgin Gorda, Anegada and Jost Van Dyke. Though smaller than each of this quartet, a fifth island is probably the most famous member of the club – Necker, the private playground that has been owned by Virgin boss Sir Richard Branson since 1979.
Main reason to go:
A guaranteed suntan, and the sense that you are holidaying somewhere rather exclusive. “Is that [insert name of so-hot-right-now movie star] on the deck of that yacht over there? No, the big one. I’m definite it is. Not sure that’s his wife.”
Best bit:
Mount Sage, the peak which brings Tortola to a head at 1,716ft (523m), and has been protected as a national park (bvinpt.org/sage-mountain) since 1964. Hikers can access the trail head from the archipelago capital Road Town. The views are remarkable.
How to do it:
Inspiring Travel (01244 729 702; inspiringtravel.co.uk) offers holidays to the Rosewood Little Dix Bay hotel; a suitably sumptuous retreat burrowed into the west coast of Virgin Gorda. A seven-night getaway costs from £6,244 per person, including flights.
1. Bermuda
British since:
1612 (founding of first settlement, Virgineola – now St George’s)
Where is it?
Contrary to occasional opinion, not in the Caribbean. It is the best part of 1,000 miles from Bermuda to the planet’s most sun-kissed holiday region (958 miles if you are marking the distance between the Bermudian capital Hamilton and its Puerto Rican counterpart San Juan); the nearest landfall is actually North Carolina, “just” 643 miles to the west. Still, despite its mid-Atlantic location, Bermuda offers plenty of Caribbean traits – gorgeous beaches, year-round warm weather, the occasional hurricane.
What is it?
Less an island, more a collection of them; 181, in fact, linked by little bridges and roads – into what appears to be a single splendid landmass, of some 21 square miles.
Main reason to go:
That reliable sub-tropical climate, mixed with a solid dose of history. Four centuries of Britishness (initially Englishness) have left their mark on Bermuda, in a haze of red telephone boxes and general gentility. St George’s, that initial footprint, is especially pretty; a contemporary of Jamestown (in Virginia) where St Peter’s Church and the State House – the former Parliament – still sing sweetly of the early 17th century.
Best bit:
The Royal Naval Dockyard (dockyard.bm), the 18th century fortress which served as Britain’s mid-Atlantic watchdog between 1795 and (to a certain extent) 1995. Fully restored, it is now dozing through its retirement as a nest of shops and restaurants.
How to do it:
A seven-night stay at the four-star Grotto Bay Beach Resort costs from £1,479 per person, including flights, via Tropical Sky (01342 395 295; tropicalsky.co.uk).
