I found the billboard for Gun Wharf while examining the original image of Portsmouth harbor and decided to try an improvement. I recreated the sails by starting with a filled rectangle and then masking off sections with ellipses. This base was then duplicated and re-sized to make one three-sail mast. I added a third sail and some shading, then duplicated the group twice and re-colored And, yes, I know the pennants should be fluttering in the other direction, but we have artistic license here -- just pretend the ships are on a tack or something. The font is Casablanca Antique with a black stroke. The background is a stock picture of clouds run through successive cutout and blur filters.