The City of San Cristóbal de la Habana, or Havana, as it looked ca. 1850. At the time the most heavily fortified city in the Americas. About 100,000 souls lived within its walls, and fairly uniquely, that is roughly the same number of people who live there today, in Old Havana. 
Up until maybe 1800, the walls and the need for defenses kept the city from sprawling, but already by 1850 there are plans forming to build a city ten times its size. Then as now, the sprawl is less thought out: there are no real centers, no squares, few churches, monuments, etc.
The buildings are very well designed for its climate: tall ceilings, tall windows, to make the hot and humid summers tolerable. And look at the streets, the awnings that hang from buildings on both side, creating shaded covered streets for the foot traffic that dominates it.
These awnings were still in use in the 1890s, when these photos were taken. The awnings could be raised or lowered, depending on the season and the weather. The sidewalks are raised and the streets clean and well maintained.
The city was already large, but not larger than that any point in the city could be reached from any other point in under 30 min. on foot, at an area of about 1.54 km² (0.6 mi²). It had some avenues, but most streets were narrow with tall one to three story buildings to shade it.
Commercial and public buildings often had lofty two story tall arcades or porticos where businesses and pedestrians could find shade and convenient place for commerce, most squares or plazas were surrounded by these.
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