Port guide: Gibraltar

This tiny town wedged into the coast of Spain is a weird, anachronistic territory with a fabulous history, terrific views and one big rock.

Who goes there
The British Overseas Territory generally features in western Mediterranean itineraries that depart from Barcelona or Rome and take in Spain, France and Italy. Other cruises dodge around Portugal and head towards Southampton. It’s usually bigger ships from Cunard, Holland America, Princess, Norwegian and the like that visit, but smaller ships from Azamara, Regent Seven Seas, Seabourn and Silversea also put in appearances.

Sail on in
Anyone who finds an iota of romance in maritime history will love the arrival in Gibraltar, associated with many British naval exploits. For a start, if you’re sailing from the west you pass through the Strait of Gibraltar, a hazy Morocco and Spain to either side. Then you sail into a bay (the Bay of Algeciras or Gibraltar, depending on your political persuasion) under the distinctive profile of the looming Rock. Splendid.

Berth rites
Gibraltar’s cruise terminal at North Mole won’t win a beauty contest but is efficient, and supplies a tourist information facility, bar and cafeteria, and a few gift and duty-free shops. It’s a 20-minute walk to the town centre, or you can hop on a paid shuttle. Expect fussy security with X-ray machines and metal detectors. Best not to carry much ashore.

Going ashore
Casemates Square, Gibraltar’s answer to a plaza, is a rare open space in this cramped territory, and is surrounded by 18th-century barracks reimagined as cafes and bars. From there you can amble through the town to admire more Georgian-era buildings and British-style pubs. Gibraltar Museum gives a good account of the rock’s 40,000-year human history. Then ascend the Rock of Gibraltar where you can hike the nature reserve, see stalactite-hung St Michael’s Cave, and inspect the historical siege tunnels. Beware the aggressive macaques, known to steal food, mobile phones and sunglasses.

Don’t miss
The best thing about the Rock of Gibraltar are the plunging views and distant squints at Morocco. No better place for the panorama than the Skywalk, wedged into the clifftops at 360 metres above the sea and with great outlooks onto further lumps of the Rock. Laminated-glass floors and open-mesh steps test the nerves. Visitors are limited to 50 at a time, so you might expect a wait.

Get active
The heart-banging Upper Rock has numerous hiking trails that won’t only give you a workout but supply gobsmacking views and historical sites too, such as the ruins of a Moorish castle and World War II fortifications. The biggest challenge – not least to your vertigo – is the Mediterranean Steps, best tackled in the early morning before it gets too hot. The sometimes-narrow path skirts cliff edges and then zigzags upwards, finishing at an old gun battery.

Best bites
Gibraltar is an old-fashioned slice of Britain with too much emphasis on pub food, but if you hanker for a baked potato, steak-and-kidney pie or roast dinner with gravy, you’ll be in 1960s heaven. Plenty of afternoon teas are on offer too. Fortunately, you can find some relief at Amar’s, a Jewish bakery founded in 1820, and La Tapilla Sixtina, which dares to provide tasty Spanish tapas.

Further afield
You’ll surely want to check out this quirky and unusual place, and so have little reason to go further afield, especially as border checks are tiresome (though apparently soon to be phased out) and this immediate corner of Spain has few attractions. Nevertheless, some excursions will take you to upmarket resort town Marbella, to farms to learn about cork production, or on dolphin-watching trips.