Gibraltar’s Old Town & History: Casemates, Main Street & the Tunnels
A walking guide to Gibraltar’s Old Town — Casemates Square, Main Street shopping, the Gibraltar Museum, the Great Synagogue and 300 years of siege history — the perfect second day on the Rock.
After a day on the Upper Rock, day two belongs to the town below it. Gibraltar’s Old Town is a compact, walkable tangle of British and Andalusian influences — red pillar boxes and tapas bars, a 1724 synagogue and a Marks & Spencer — layered over three centuries of siege history. Here’s how to walk it.
Start at Grand Casemates Square#
The big square at the north end of Main Street, set in early-19th-century barracks, is the Old Town’s social heart: cafés, terraces and the venue for concerts and National Day. It’s about a 12-minute flat walk from Marina Bay and the natural place to begin.
Walk Main Street#
From Casemates, pedestrianised Main Street runs the length of the Old Town — a run of shops, cafés, plazas and churches. It’s long been famous for tax-free shopping, though a change in 2026 has narrowed that advantage (below).
The history in a nutshell#
Gibraltar’s strategic position has made it fought-over for millennia, and the town wears that story openly. A quick timeline helps the sights make sense:
- Neanderthals. Gibraltar’s sea caves were among the last known homes of Neanderthals — the Gorham’s Cave Complex is a UNESCO World Heritage Site, and the Gibraltar Museum tells the story.
- Moorish & Spanish Gibraltar. The Moors built the castle whose Tower of Homage still stands (currently closed for works); Spain held the Rock before 1704.
- The Great Siege (1779–83). The defining episode — a nearly four-year siege that produced the Great Siege Tunnels up on the Rock.
- A WWII fortress. In the Second World War the Rock became an underground garrison for 16,000 troops, with tens of kilometres of tunnels.
What to see in the Old Town#
| Place | What it is |
|---|---|
| Gibraltar Museum | The story of the Rock from the Neanderthals on, with 14th-century Moorish baths beneath |
| Great Synagogue | Founded in 1724 on Engineer Lane — among the oldest on the Iberian Peninsula |
| King’s Chapel & the Convent | The Governor’s residence and its chapel; time it for the changing of the guard |
| Trafalgar Cemetery | A leafy, atmospheric graveyard from the Napoleonic era, just outside the old walls |
| Cathedral of St Mary the Crowned | Gibraltar’s Catholic cathedral, on the site of a former mosque |
| City Under Siege | An open-air exhibition of soldiers’ life (and original 1720s graffiti) up on the Rock |
Opening hours vary — check locally, especially on Sundays.
Where to break for lunch#
The Old Town is full of good stops — a chippy tea at Roy’s on Casemates, a Spanish lunch, or a pint in a historic pub. We round them up in the Gibraltar restaurant guide. This day is the middle leg of our three-day itinerary.
Frequently asked questions#
What is there to do in Gibraltar’s Old Town?
Walk pedestrian Main Street from Grand Casemates Square, visit the Gibraltar Museum and the 1724 Great Synagogue, watch the changing of the guard at the Convent, and explore the Trafalgar Cemetery and the town’s churches — an easy half-day on foot.
Is shopping in Gibraltar still tax-free?
Gibraltar has no VAT, but a 15% transaction tax introduced on 10 April 2026 (charged to businesses at import rather than at the till) has narrowed the old duty-free advantage. Prices can still be competitive on some goods, but compare before you buy.
Did Neanderthals live in Gibraltar?
Yes — Gibraltar’s sea caves were among the last known Neanderthal habitats, and the Gorham’s Cave Complex is a UNESCO World Heritage Site. The Gibraltar Museum explains the archaeology.
How long do you need in Gibraltar’s town?
About half a day to stroll Main Street, see the museum and a couple of sights, and stop for lunch — ideal as day two after the Upper Rock.