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Doing map assignments are certainly fun, but a lot of work too, because the map usually must also include many little icons as a client requirement. Posted here is a recent map image I created for art director Carolyn McClain at Crain's New York Business Weekly -focussing on the downtown financial area of Manhattan. (New York City)
The image was done by painting a background shape (in gouache on watercolor paper) of the island area and the water... and also a simple black line-drawing of the Statue of Liberty, and scanning everything into Photoshop... where I then, in separate layers, created all the icon elements using simple Photoshop tools: people, buildings, food, boats, bridges, birds, textures, etc... Since everything was in layers, I could then easily adjust and fine tune the location of all the elements by moving them around.
Posted above is the full map image, as well as a detail view of a section, so you can better see the detail and textures. As usual, the project was under the time gun... but it came out very well.
An advertising agency in Dallas saw the image, and it almost obtained me an annual report project for one of their clients... but unfortunately I did not get that project. Oh well... you win some and you lose some!
Remember, all you illustrators out there, to negotiate a sufficiently higher fee when offered a map project, because all the related little icons you'll be doing are going to take more time!