City of London

A first trip to the City of London usually starts with walking the old Roman boundary itself: past St Paul's, along streets with names like Cornhill and Cheapside that tell you exactly what used to be traded there, and down towards the Thames where the skyline turns properly modern. It is a strange, layered place, mediaeval churches wedged between glass towers, and most visitors spend a day simply following that contrast rather than ticking off a list.

Few people stay overnight in the City itself, since it empties out at weekends and works as a day trip from wherever you are actually based in London. That emptying out is part of the appeal: come on a Saturday and you get the architecture, the alleyways, and the riverside without the weekday crowds of commuters.

Beyond the walking, the main thing to do here is eat and drink well in buildings that have seen centuries of trade. Wine bars have taken to the City with particular enthusiasm, places like Humble Grape Bow Lane and Bar Douro City tucked into old cellars and railway arches, pouring bottles you would not expect to find near a bank. Cloth Cornhill and Terra Rossa La Cantina add to that same seam of relaxed, wine-led spots built for long lunches rather than quick pints.

With 145 restaurants listed across the Square Mile, the choice is wider than the City's reputation for expense-account lunches might suggest. It rewards picking a direction and wandering, since a five-minute walk here can take you from a Roman ruin to a modern wine bar to a church that has stood since before the Great Fire.