Time for the holiday shuffle again. We originally booked an October trip to the Paris Motor Show but that went down the plughole months ago. A short break in Sardinia was the next option, and then Italy introduced testing for UK visitors – too much hassle. Just take me anywhere in Europe, says the husband, no more staycations – life at home is so depressing right now. A bit of sunshine won’t go amiss either. That’s a big ask in 2020.

Gibraltar is one of the very few restriction-free destinations for Brits right now and I have to say I’m intrigued. A little chunk of England tacked onto southern Spain – it’s so unlikely, and so contraversial. Plus it has the only wild monkeys in Europe, October temps in the mid twenties and lots of reward flights available. At a grand cost of £1 each for BA Club Europe – let’s go!

It’s amazing how the novel quickly becomes routine. Masks in the taxi, the terminal, the plane, whatever. Ordering through an app, totally normal. We have a smooth BA travel experience, with a particularly cheery flight attendant. I suppose he’s happy to still have a job, hence he’s dishing out the champagne with wild abandon. Arriving in Gibraltar, we grab a cab to take us through town to our hotel. It’s not far, but it’s all uphill.

The Rock Hotel high in the Upper Town is a Gibraltar institution. Built in 1932 in Art Deco style, it quickly became a magnet for the rich and famous, and is considered to be one of Europe’s most iconic hotels. From Winston Churchill and Errol Flynn to the Two Ronnies, everyone has stayed here. John and Yoko got married at The Rock, and Sean Connery stayed at the hotel on his wedding night.


Upon arrival, you can have great fun playing Guess Who? The lift lobby has become a Hall of Fame of celebrity guests. Cyndi Lauper, Bob Geldof, Brucie, Alex Ferguson, Judith Chalmers, Elaine Paige. There’s someone for every taste! We’re usually in a hurry to get up to our room and unpacked, but not here.


The hotel may have lost a bit of its sparkle nowadays – the decor is looking quite tired – but it still has atmosphere galore. Personally, I prefer to stay somewhere with a bit of history and character than the most immaculate and snazzy chain hotel. In the bar, I’m wondering if Ernest Hemingway once sat in my seat. I ask for a G&T. I only do doubles, warns the barman. This place is perfect!


Our room is simple but huge, with a canopied bed, and a lovely big balcony. Plenty of hangers too, hurrah! I’ll never understand why many places think two per person is adequate. From our balcony, the views go on forever. Straight ahead is Spain, over to the left is Morocco. I could sit out here all day.


But no, there’s serious exploring to be done. I’m dying to experience the town – is it Spanish, is it English, or something in between? Gibraltar has changed hands many times over the centuries, it was Mons Calpe to the Phoenicians and Jabal Tariq to the Moors before becoming part of the Kingdom of Spain. When the Spanish throne fell vacant in 1700, the War of the Spanish Succession broke out in Europe over who would take power. Gibraltar was the price of Britain’s withdrawal in 1704. I think we got a good bargain!


Since then, the Spanish have been trying to regain the Rock, and you can’t blame them. Gibraltar’s strategic location at the entry to the Mediterranean makes it a valuable asset for whoever holds it, and it has long been fortified to ward off aggressors. Old bastions, tunnels, gates and gun batteries are evident all over town. They’re all neatly labelled too, so helpful!


Spain fought hard to take back Gibraltar over the course of the 18th century. The Great Seige of Gibraltar in 1779 lasted for more than three years and was so destructive that the whole town had to be rebuilt, but the territory remained British. We don’t give up that easily.

In 1969, the Spanish tried the less overtly aggressive approach of closing the border, only opening it fully again in 1985 to gain entry into the EEC (now the EU). But the British are loath to give up what has long been an important Royal Navy base and the people of Gibraltar have always voted to remain British. Hands off our Rock, España.

It’s still a contraversial issue between the two countries, complicated now by Brexit – the population of Gibraltar voted overwhelmingly to remain in the EU. The territory needs Spanish workers, with around 15,000 crossing the border on a normal day. With only one entry point, you can see why any delays would cause massive headaches for all concerned. At present, there appears to be an uneasy truce in place, but for how long?

Strolling along the pedestrianised Main Street, I’m expecting to see lots of familiar retailers. I’ve heard that expats in Spain usually flock over the border to get British goods they just can’t do without. In reality, I’m surprised at how Spanish it feels here. Yes, there’s M&S and Debenhams but there are also many small independant stores. There are British style pubs, but mixed in with tapas bars and pavement cafés. Besides, it’s too warm to feel British.


Also strung out along Main Street are some of Gibraltar’s most impressive civic buildings – the Governor’s Residence, the Cathedral, the Law Courts, Parliament House and City Hall. It’s clearly the place to join in that favourite European pastime, aimlessly sauntering. Whole families walk together, and people call out to one another across the street. It feels like a tight knit and friendly place to live. Around 33,000 people live here, so it’s only a medium sized town by UK standards.

Main Street eventually takes us to Casemates Square, a central gathering spot dominated by the old military barracks, now converted into cafés, bars and shops. I can say with conviction that it’s a good place to order a drink and people watch. I recommend the white sangria at Café Solo. The sacrifices I make for research!


Just behind the Casemates barracks is the fascinating Landport Tunnel. This was originally the only way in or out of Gibraltar, apart from by boat. It was closed every night by pulling up the drawbridge and closing the gate at the Spanish end. The Landport was heavily guarded, with a moat, iron spikes and a gunpowder mine, to say nothing of the 20 guns ready to fire from above on anyone getting too close. Nowadays it’s more of a commuter route, with people going in and out of the walled city to work.



Going out in Gibraltar is a casual affair – as the weather is so good most people sit outdoors to eat and drink right into the evening. We have dinner at Cafe Rojo in Irish Town which has a menu full of interesting options. They taste as good as they sound too. The origins of the street name are a bit of a mystery, as no-one Irish appears to have ever lived here. Back in the day, it was referred to as an area of ill repute, but it feels perfectly safe and respectable now.

When we emerge at about 10pm, we’re surprised by how quiet the streets are. Entertainment venues can stay open until midnight in Gibraltar, but obviously coronavirus is still keeping people at home. Luckily we’re not night owls, although I have a strange urge to stay up late just because I can!


The uphill climb to our hotel is even more strenuous after much food and wine, with the increased gradient of the driveway nearly finishing us off. Time to get some rest, as there’s a bigger climb to face tomorrow – the Rock itself. I want to meet some monkeys!

I love that ‘it’s too warm to feel British’ hahaha. I have never thought about visiting but it looks so beautiful, I might just have to! What a great trip. Thanks for sharing
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It’s an interesting place, we really enjoyed it. Thanks for the feedback!
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Great blog Steph. We went to Gibraltar for the day in June 1999 as a day out during our honeymoon. Unfortunately we didn’t like it quite as much as you do!
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Perhaps I’m more easily pleased? At the moment I’m just so glad to escape the gloom!!!
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