I arrived in Gibraltar with one very clear objective: climb the Rock and see the monkeys. Less than 24 hours later, I left Gibraltar having neither climbed the Rock nor laid eyes on a single monkey. Ordinarily, this would probably represent fairly poor travel journalism. In my defence, quite a lot happened in between.

I'd travelled out to visit Enchanted Princess, which was in port for the day, and experience Princess Cruises' 360 dining experience onboard. This meant my introduction to Gibraltar would be brief. Somewhere between arriving, checking into a hotel, boarding a cruise ship for a seven-course dinner and flying home again, I intended to squeeze in one of Europe's most recognisable landmarks. It seemed entirely achievable at the time.

Arriving in Gibraltar starts with walking across a live airport runway

Gibraltar Airport is tiny enough that you land with the slightly disconcerting feeling that everybody on the peninsula is aware that you've just arrived. Then, after leaving the terminal, you conspicuously walk across the runway you have just landed on.

This isn't a lapse in local infrastructure planning. Pedestrians and cyclists really do cross an active runway to reach the city, with barriers closing when aircraft need it. Gibraltar's tourist board offers official guidance on how to do so safely, including the rather fun instruction not to linger taking photographs because a plane may shortly require the bit of ground you're currently standing on.

Coming from a British airport, where getting within 40 metres of an aircraft usually requires a passport, a boarding pass and the removal of your belt, strolling across the tarmac with my suitcase felt illicit. It also sets the tone for Gibraltar rather efficiently. On the other side of the runway is the Rock, looming absurdly over a place small enough that almost everything seems to happen underneath it.

Gibraltar weather: hotter than the thermometer suggests

Technically, Gibraltar was cooler than Bristol, where I'd flown in from, when I visited. My bodily reaction to the climate told a different story.

The humidity seemed to add approximately 40 degrees and, within minutes, I had acquired the sort of permanent sheen you might usually associate with glazed ham. So while the thermometer may look reassuring, don't trust it entirely. Bring water, wear something breathable and accept early that your hair will be plastered to your forehead within moments.

Staying at The Eliott Hotel in Gibraltar

Thankfully, I was staying at The Eliott Hotel in the Old Town, which was lovely. It has comfortable rooms, good food, a relaxed atmosphere and a rooftop pool overlooking the city, harbour and Rock. The hotel's Rock Salt restaurant is up there too, along with a solarium one floor above.

The pool deserves special mention because it had one of the more strangely liminal atmospheres I've encountered in a hotel. There was nothing wrong with it. Quite the opposite. It was attractive, sunny and peaceful. But something about swimming on a very quiet rooftop while this enormous limestone monolith rose nearby and the rest of Gibraltar sat eerily below made it feel faintly like I'd entered the holiday level of a PlayStation game after everybody else had logged off. I liked it enormously.

What Gibraltar actually feels like

Then I went for a walk and Gibraltar became considerably stranger. Visually, your brain insists you're somewhere in southern Spain. There are palms and sun-bleached buildings, shutters, tiled façades and narrow lanes. Spanish chatter drifts past. The Mediterranean sits at the bottom of the street.

Then you turn a corner and there's Marks & Spencer. Carry on and you encounter Morrisons. Further down the street, there's a sale on at Matalan, the effect is destabilising.

This mixture has rather deeper roots than a few imported supermarkets. Gibraltar's modern population developed through British, Spanish, Genoese, Maltese, Portuguese, Jewish, Moroccan and other communities. English remains the official language, while the local Yanito vernacular freely combines English and Spanish. Its architecture similarly picks up Spanish, Moorish, Genoese and British Regency influences.

Main Street makes all of this particularly visible. Traditional businesses sit alongside extremely familiar British chains, with everything from M&S and Holland & Barrett to NEXT and Morrisons among the local shopping options. It feels less like Britain transplanted to the Mediterranean than southern Spain having had a recurring and slightly inexplicable encounter with an early 00s British high street.

Casemates Square and Gibraltar's strangely disguised chain restaurants

The oddness reaches a particularly enjoyable pitch around Casemates Square. Historically, this was a military space beside the British-built Grand Casemates barracks. It has also, less cheerfully, hosted public executions. Today it's a large pedestrian square lined with outdoor tables, cafés, restaurants and bars. But what particularly threw me about the area was the signage.

Some quirk of planning means familiar chains don't always announce themselves with the visual violence we're accustomed to at home. I'd walk towards what appeared, from a distance, to be an unexpectedly elegant café with tables spilling into the square, only to get close enough to discover I had found a Costa Coffee. Another handsome frontage revealed itself as Burger King. It became a recurring game.

Gibraltar doesn't conceal these places exactly. It just gives them enough dignity that you'd be forgiven for being briefly fooled into thinking somebody's about to bring you grilled sardines as opposed to a Whopper.

Can you see the Rock of Gibraltar in one day?

Yes, you can see the Rock in one day. I know this because practically every piece of official advice says so. I also know this because I didn't manage it.

The Upper Rock Nature Reserve rises to 426 metres and contains many of Gibraltar's headline sights, including St Michael's Cave, the Great Siege Tunnels, viewpoints and the Barbary macaques. Gibraltar is the only place in Europe where Barbary macaques live freely in the wild.

The tourist board's 24-hour itinerary recommends making the Rock the priority and says a basic guided tour can take around an hour and a half. Exploring it more thoroughly on foot takes considerably longer. I had intended to walk up and I genuinely tried to make the timings work. I did look at the Rock repeatedly, which I feel should count for something.

But between our arrival, the programme onboard Enchanted Princess and the small matter of needing to get back to the airport the following day (and fit in several G&Ts in between), the window simply disappeared. The monkeys remained up there, presumably indifferent to my loss.

It's the one thing I'd change about my visit. If you have a genuine 24 hours rather than a press-trip approximation of 24 hours, do the Rock first and then plan everything else around it.

A Gibraltar dolphin tour is apparently worth making time for

There was another activity I missed which caused considerably more smugness among the people who hadn't. Several of our group went dolphin watching in the Bay of Gibraltar and returned talking about it as one of their favourite travel experiences to date. Dolphin-watching boat trips are among the territory's principal attractions, and it's easy to fit one into a short stay because departures operate directly from the bay rather than requiring an expedition inland.

I can't personally tell you whether it was brilliant because I was elsewhere (at a wine bar) at the time, maintaining my impressive record of failing to see Gibraltar's charismatic wildlife. But the rest of our group came back sufficiently evangelical about it that it's now high on my list for round two.

Dinner aboard Enchanted Princess

The reason I was in Gibraltar in the first place was waiting in the harbour. Princess had invited us onboard Enchanted Princess to experience 360: An Extraordinary Experience, its immersive dining concept available aboard Enchanted Princess and Discovery Princess.

It is, officially, a seven-course multi-sensory dinner using food, wine, imagery, sound, scent and storytelling to move guests through different parts of the Mediterranean. In practice, it’s also far more impressive and involving than that description makes it sound. The circular venue takes just 20 guests per sitting, with projected imagery surrounding the table as the meal moves through places including Santorini, the Amalfi Coast, Barcelona and Provence. It’s ambitious, beautifully executed, choreographed and, at points, quite transportive.

It also helped that I was sharing the table with an excellent group, including (but not limited to) Katie Woods, Andy Clarke, Jess and Ludo, Jamie Robins and John Torode. I’ll be writing a full review of 360 for Cruise Collective soon, because there’s quite a lot more to say about it than I can reasonably wedge into a piece about Gibraltar's many quirks.

So there I was, eating my way virtually around the Mediterranean aboard a cruise ship in Gibraltar, having spent the previous few hours sweating past M&S beneath a 426-metre limestone monolith. By this point, the trip had developed an internal logic all of its own.

What should you actually do with 24 hours in Gibraltar?

With the benefit of hindsight, I'd resist trying to turn Gibraltar into a miniature sightseeing endurance event. Perhaps I'd do the Rock early, the main bit I missed, and the mistake I wouldn't repeat.

Afterwards, I'd walk rather than looking for transport. Main Street, Casemates Square and the lanes of the Old Town are compact enough to explore without much ceremony, and wandering is where Gibraltar's peculiar cultural collisions become most apparent.

If wildlife appeals, a dolphin trip from the bay could fit comfortably into the remainder of the day. Then I'd eat somewhere, have a drink and allow some spare time for simply looking around. Gibraltar is too strange to experience exclusively through its obvious attractions.

Is Gibraltar worth visiting for 24 hours?

I think 24 hours is probably the perfect amount of time to spend there. Not because that's necessarily enough to see all of it. Evidently, I couldn't even manage one large rock. But a compressed timetable suits the place. 

I landed on a tiny strip of runway, walked across that same runway with my suitcase, sweated profusely in weather ostensibly cooler than Bristol, swam in a rooftop pool that felt detached from reality, repeatedly discovered British chain stores disguised beneath Mediterranean architecture, ate seven courses aboard a cruise ship and then left again.

The whole thing now has the quality of a dream somebody would describe to you at breakfast. “You were there. And John Torode was there. And there were monkeys, except you never saw the monkeys. And then the café was actually a Burger King.”

I still need to climb the Rock, of course. Which is irritating but also a reasonably good reason to go back.

Henry travelled to Gibraltar as a guest of Princess Cruises. Cruise Collective retains full editorial control over its coverage.