Well... I started by looking at google earth and pictures of Santo Domingo today. There are a lot of beaches... and palm trees... and babes and margaritas...
Then I found a few historical maps and tried to make it look a little more like that.
There are a few problems with that though. I scaled it down due to not wanting a town covering half of the game area. The actual harbor seems to have been up the river and I wanted to show it as a harbor without covering half the gaming area with land. In the historical drawings it doesn't look like sandy beaches, though. An easy fix might be gluing some rocks on the beaches along the town, a little like what it looks like in the first picture below.
1785
1805
1912
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