1980s retro t-shirt showing journey through 3 cities

This is what a business in United States was looking for in their t-shirt design

We need a t-shirt image to celebrate someone's birthday. We are looking for a 1980's design aesthetic. The image will convey the journey he has taken in life so far and will show a man sitting on the hood of a gray 1999 Acura TL at the end of a winding road. The road started in Seattle, went through New York City, and finally crossed the Golden Gate Bridge. Please put the text "Ajayfest 40th Anniversary" somewhere around the top of the image (it can be on 2 separate lines like "Ajayfest | 40th Anniversary"). Attached photo is for inspiration for the guy's head/upper body - he looks like this person. Read more