Far from London, in San Francisco I found that yellow cab drivers could often (but not always) take me to where I wanted if I gave a cross street or described an area of the city. Uber and Lyft often couldn't because Google Maps is surprisingly unreliable when it comes to searching for cross streets. Just my house was an example, yellow cabs I could usually tell the cross street and they knew it immediately, and Uber/Lyft I usually had to give the full address and then wait while they typed it in. Part of this is because humans can retain a lot of location-specific intuition - I lived at the intersection of a regionally important through street and a university. Cab drivers knew the through street, and knew what part of it the university streets were in... the rest was just driving down it until they saw the right university.
I also had a LOT of experiences with Lyft drivers that were clearly very new to the city and lacked basic awareness of unusually set up but major intersections, and near-rush-hour traffic patterns. This lead to things like going the wrong way on one-way streets and missing turn lanes.
Software still has a long ways to go before it can adequately capture and work with that type of region-specific organization.