Upon the recommendation of several people I ended up buying a pair of TOMS for my trip.
I've never been that into these shoes and honestly have always thought they were ugly, but oh my god they are fabulous. They're SO COMFORTABLE and really do go with just about everything. I wear them to work with slacks even.
Just a few days after I ended up buying these:
I'm also taking along a pair of cognac riding boots I picked up at Old Navy.
The weather will mostly be in the 50s and 60s and there may be some rain so they'll definitely come in handy.
Thanks again for all the suggestions!