Not 40 miles from bustling high-tech Hong Kong is sleepy crumbling Macau. You wouldn’t notice much difference to look at an atlas or a history book; the two places seem similar enough be twins. But in the flesh, they are as different as night and day.

Geographically speaking, they have sprung from the same DNA. Both of these city-states are comprised of a cluster of islands. Both were acquired by European powers through force, Macau by Portugal in 1557 and Hong Kong by England in 1842. And both of them were returned to Chinese control in the late nineties as Special Administrative Regions (SARs.)

Each has only a narrow stripe of water, no wider than the Mississippi, dividing them from China. But they have more in common with each other than with the mainland. They both speak Cantonese. They both drive on the wrong side of the road. They both have a large number of European residents: about one for every five Chinese. They both have local TV stations that broadcast in English. Their people idolize the Japanese, whereas the mainlanders shun the Japanese and favor the Koreans.

So I was shocked to step off the Hong Kong ferry and into the strange world of Macau.

The first thing I noticed about Macau is what it doesn’t have. Gone are the rude and inescapable crowds. Gone is the glow of shiny towering buildings, competing with each other in height, radical design, and candle-power.

In only a few parts of Macau do you even notice a crowd, and it only gets cramped around some ill-conceived repair work, where the sidewalk is reduced to a splinter. The only tall buildings in Macau—with the exception of the cement-cast Macau Tower—are casinos. Most of the casinos are the sort of two-bit joints one associates with sin and poverty. But right now, the island’s principal occupation seems to be building huge new gambling palaces. Many of these have a Vegas pedigree, like The Venetian and The Sands.

As for the rest of Macau, well… Both cities have economically turbulent areas, but Macau is dominated by them. Leave the small but tidy path that runs through the casinos, the main shopping district, and the few historical offerings, and the place becomes an endless ghetto. Cement high-rises are stained with dirt and paint. Road are filled with as much gravel as the original pavement. All around the islands, there are giant inexplicable holes in the ground.

Evidence of crime is everywhere in Macau, from the security cameras all over my hotel to the fully barred apartment porches—even six stories up. There is a piece of paper taped to the windows of Macau’s only Starbucks declaring, “Burglar Alarm Installed.” The sign feels personal, telling whoever it is that broke in the last time they had better not try it again. No doubt the west’s largest coffee chain—with branches smeared across Hong Kong—were shocked to find that ten years of Chinese rule had done little to against the four centuries of Portuguese influence.

And I think it is in the lineage of these two cities where we can find the answer to their deep-rooted differences. The British like to make money, and they are good at it. They turned Hong Kong into the gateway to Asia, a neutral ground where manufactures of everything from clothing to electronics clamor to get their good into Western markets. And the British took their modest cut.

Portugal, on the other hand, is often referred to as the “the third world of Europe.” They have enough of their own troubles without having to worry about some run down island on the other side of the planet. No doubt the administrators they sent ran things the way they did at home, with little more aspiration than to squeeze a few patacas out of their ancient colony. In fact, walking around Macau, I experience déjà vu from my trip to Lisbon. Even half-way round the world, the apple hasn’t fallen far from the tree.

And perhaps this is why, while the British had to be cajoled into giving up Hong Kong, Portugal offered Macau back several times before China begrudgingly took it from them.