Well, I am happy to report back that I have found the perfect shoes and your help was SO, very appreciated!
My good friend over at Newlyweds Next Door was also preparing for a big Europe trip and she mentioned that she ordered a bunch of shoes offline and then mailed back the ones she didn't like. I loved this idea and decided to place a big order with Zappos. Here are the 6 pairs I decided to try, based on recommendations from you all and reviews on their website...
Sperry Top Siders, Teva Kayenta, Merrel Oceania in Lava, Ahnu Paris, Merrel Marina in Brown, and Privo Kulin by Clarks
My big box of shoes!
After trying them all on, I had to admit, that I was pretty much pleased with every pair. There were some I loved more than others, but there was nothing I really disliked. I decided right away that I was going to keep the Tevas.
I wanted good pair of sandals that I could walk miles in. These are a great pair! I was tempted to order a pair of Chacos (so many of you recommended these!), but I just liked the look of these. I wore them on our field trip to Jamestown last week, and they definitely made a great pair of walking shoes.
When it came to picking a pair of "flats" (my non sandal), I had a much harder choice. After initially trying them all on I narrowed it down to the Merrel Marina and the Clarks. I can't even begin to tell you how comfortable these shoes were! Both pairs had great arch support and were super comfy.
I kept the shoes for a week, tried them on every day, even took them home to my parents for a weekend to get my mom's opinion. It was a tough decisions people! I really loved the look of the Merrels. They looked like boat shoes, but I found them to be much more comfortable than the Sperrys. I'd highly recommend them. The Clarks were equally comfortable, maybe even more. Can you see the little raised dots in the sole? Those are like little massagers for your feet. Incredible!
In the end I went with the Clarks. I felt like they were a little "snugger" and when I'm doing a lot of walking, this is what I wanted. It killed me to ship back the Merrels (seriously, I loved them!), but I have a feeling I may be ordering them in the future. I just couldn't justify spending all the money at one time.
Also, just a little shout out to Zappos. BEST SHOE BUYING EXPERIENCE EVER! They made the process so easy. The shipping was fast, the return and refund process was simple, and I would buy more shoes from them in a heartbeat. In fact, 3 of my pairs were a half size too big, so I reordered them on a Wednesday and had them by Friday thanks to a free upgrade for my UPS shipping. This made me never want to visit a shoe store again! My only complaint is we didn't have enough room in our living room for all the shoes (J ordered 7 pairs too!). 16 pairs of shoes + boxes in one living room was a bit much, but well worth it to have it all delivered to your front door!