To that end, I highly recommend the Ahnu Montara. I tried a pair of these high topped boots on at our local REI and then ordered them online because REI didn't have the color I wanted. They are not for serious mountain climbing, but they are very comfortable and saw me through about 6 weeks in Istanbul, Greece and Italy last fall.
I later learned that my daughter wore a pair of them on an archaeological dig on the Swedish island of Gotland. They worked exceptionally well and were very stable in the wet, mud and manure as she worked. Whatever you decide to wear, be sure to wash off as much of nature as you possibly can for the trip home. There can be questions about that when you return.
In terms of packing, I wore mine on the plane over and back, well, actually just about all the time everyday except at the end of the day when I would usually change into a different pair of shoes for the evening. In addition to the typical cobblestones and very rough terrain at some Greek ruins, my boots got me through lots of rain on our trip. They sound like they are not totally waterproof, but I waded through puddles and never got my feet wet.
In terms of fashion, they are boots after all, but there are some great colors and all that was visible of them was the toe and bottom under the hem of my pants. One strange phenomenon, they made my feet look smaller. I wear a 9.5 in this boot.
There are lots of great, light weight boots similar to these out there. I tried some of the other brands, but these were comfortable from the beginning. Thank goodness for today's technology. On my first trip to Europe in the late 70's I wore very heavy, leather Vasque hiking boots to muck around the areas you are going. They worked well, but even with waterproof spray, they got wet and and never really got dry.
I also have a pair of the short Ahnu Montara II hiking shoes. They are truly waterproof, they don't seem to breathe like the high tops and they certainly aren't as stable or as comfortable on me. And they don't work as well with my socks. I needed a 10 in these, and they don't make my feet look smaller!
I wear Sockwell Circulator compression socks. They are made of "cashmerino" and breathe well regardless of the environment outside your shoes or boots. There are many brands of socks that blend wool with synthetics for the best temperature and moisture regulation. My sock drawer is full of other sock experiments, but these are the ones that work the best for me.
If you can find a pair of boots that you feel comfortable wearing in many situations and that are comfortable on you for hours and miles at a time, you will have a much better trip overall. Enjoy the search and the trip.