Graphic for my... "ship's log"

Okay, considering that I'm Italian is not the right moment to think about "ship's log", but this is something I MUST finish quickly, since it's a long time I'm working on that.
Nothing special: I'm only preparing my little book/diary of this summer US trip. It was my sister and I, prowling about US, visiting relatives there (wonderful enlarged family).
I wrote everything day by day, inserted pics in all the pages but... I needed something to introduce every city I visited, starting from Milan.
These are each chapter covers - let's say.
I decided to work on a very simple graphic, very similar to the most common indication involving the little human shapes.

Double issue:
° how to represent my sister and I in a general , turistic, generic way?
° how to "zip" a city in few symbols?

The wedding of my cousin Shannon - no way to symbolize the place, I did the event.

Clothes are FAITHFUL

 

CHICAGO

 

DC

 

JIM THORPE (PA)

 

MILAN - the starting point

 

NYC

 

PHILLY

PITT 

 

...and then (p)back home...