The one good reason to visit the British Overseas Territory of Gibraltar

The approach to Gibraltar is impressive. Thrilling, actually. The brooding rock swings into view and makes you think stirring, James Bond thoughts. Cliffs rise sheer on one side to Gibraltar's summit. Down below is a plucky town of 30,000 people who stubbornly gaze at Spain every day, yet want no part of it. They have a siege mentality behind a tall chain-link fence that looks like something from the Cold War.

I'm on an escorted journey around Spain and Portugal, and there's good reason to imagine Gibraltar might be another interesting stop. After all, it's an authentic working town on a tourist coastline. It's an endangered species, a British Overseas Territory comprising seven square kilometres of curious culture preserved by its vital strategic position. Its history is fabulous. Gibraltar has prehistoric caves, Moorish castle remains and centuries of significant military fortifications. It has Georgian architecture and two cathedrals, plus views to infinity.

Alas, none of these make it exciting, unless you have a special hankering for Britain circa 1970, when it was a dismal place still dreaming of faded glories. Gibraltar is like a strange, anachronistic iceberg that split off Old Blighty to become a dull grey splinter on Spain's sunny Mediterranean shoreline. Its famous naval facilities are much reduced, and replaced by swanky apartments that shout property speculation, and the Costa del Sol style of which wins no awards.

Gibraltar is now an offshore financial and internet gambling centre, according to our Insight Vacations travel director, Elena. So, no more swashbuckling then. The salty derring-do is gone, leaving only three-prong electrical plugs and red pillar boxes as a lingering sign of empire. The locals buy their underwear at Marks & Spencer instead of Zara, and constantly remind visitors of their Britishness. Well, our local guide, John, does anyway, even though he speaks with a strange hybrid accent that mingles East End with Andalusia.

John drives us to Upper Rock Nature Preserve where we visit St Michael's Cave and stare at the infamous macaques on the hillside. I can tell John wants us to be more excited, but the macaques don't raise the pulse of any Australian who has travelled in monkey-populated Asia. The dizzying road up is impressive, though, as are the vertiginous views. We can see most of Gibraltar, a warship afloat in the harbour, a British Airways plane landing on the runway.

We plunge back down into town, where we abandon John for our free time. I speedily conclude that Gibraltar is one of Iberia's ugliest towns. If it were in England it would scarcely rate a guidebook mention. On our Insight Vacations itinerary of flamboyant cities from Salamanca to Seville, it seems like a practical joke.

I lunch on Sunday roast accompanied by overcooked vegetables, like something served at a Birmingham motorway stop. What to see? The Convent is home to the governor and closed to the public. The Gibraltar Museum gives a good account of the rock's 40,000-year-old human history. Instead of Spain's cheerful tapas bars, there are gloomy pubs with heroic British names.

We reconvene in Casemates Square, Gibraltar's answer to a plaza and one of the town's few redeeming features. It's a rare open space, surrounded by 18th-century barracks re-imagined as cafes and bars. Above rises the impressive bulk of the Rock. For a moment, I feel a slight delight, though it doesn't last long. We must plod back past scowling immigration officers and through the cheerless chain-link fence into Spain.

As we go, Elena asks me how I liked Gibraltar. I reply that I'm glad she's brought me to this weird place. I wouldn't have missed it, although – by George! – I won't be hurrying back.

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Insight Vacations' popular 15-day Best of Spain and Portugal itinerary between Madrid and Barcelona (or reverse) runs weekly from April to October and visits destinations including Salamanca, Porto, Lisbon, Seville, Gibraltar and Granada. Prices from $4727 a person, twin share including some meals, Insight Experiences, a travel director and local specialist guides. Phone 1800 001 778, see insightvacations.com/au

Brian Johnston travelled as a guest of Insight Vacations.

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