Our time on Anguilla turned out to be surprisingly compact. We landed directly on the beach at Road Bay and very quickly realised that, in one direction, a walk along the shoreline ends at a pier you are not allowed to cross – there is a fence and a restricted service area belonging to some local facility. In the other direction, the beach gradually comes to an end, giving way to rocky outcrops.
In effect, visitors find themselves confined to a strip of coastline roughly 500 metres long. I even regretted that we had not gone to another beach: local taxi drivers were offering trips around the island for 12–40 dollars – the closer beaches cheaper, the more distant ones slightly more expensive. But I wanted to stroll along what I imagined would be a “town street”. And I was surprised to discover that there simply wasn’t one. Instead, there was a dirt road, a few modest houses, a shop, a church and a small art gallery (which, on the day of our visit, was closed).
There is no promenade in the familiar European sense, no tourist streets at all. Just sand, sea, one small café with sunbeds, and hardly any local residents in sight. That genuinely surprised me.
In the end, all the taxi drivers left, and we stayed in Road Bay and simply relaxed: swimming in the crystal-clear water, walking along the sand, and watching the boats of local fishermen.

To better understand this quiet island, it helps to know at least a few key moments from its history.

The first inhabitants of Anguilla arrived from the region of present-day South America. Archaeological evidence shows that people lived on the island as early as around 1300 BC, while permanent settlements known to scholars date back to the 6th century AD. The island had its own Indigenous name – Malliouhana.

In 1650, English settlers arrived on Anguilla. By the mid-17th century, African slaves were brought to the island to work on tobacco plantations and later on sugar estates. By the 19th century, the Afro-Caribbean population made up the majority of the island’s inhabitants. Slavery in the British Empire was abolished in 1834, and many plantation owners left Anguilla, selling their land to former slaves. Economic development remained slow, the island stayed poor, and this largely shaped its future character – without large cities, major ports, or extensive urban development.
For a long time, Anguilla was administered first through Antigua and later through St Kitts. In the 20th century, the island made several attempts to break away from an unwanted administrative union. In 1967, a movement known as the Anguillian Revolution broke out. The island effectively proclaimed itself an independent republic, and in 1980 it was officially designated a separate, self-governing British Overseas Territory.

Today, Anguilla is a small, stable jurisdiction whose economy relies on tourism and offshore services. Yet these services remain almost invisible to the casual visitor. During my walks around Road Bay, I never once saw a local lawyer’s office or a government agency. Perhaps one needs to go somewhere else on the island to glimpse that side of Anguilla’s life – somewhere tourists do not usually go.