My boyfriend and I did a hike on the Preserverance Trail in Juneau. The last portion of the hike was fairly steep, and if you are worried about ankle support, hiking boots would be good. We both wore tennis shoes and were fine (we do a lot of hiking and I wear both hiking boots and tennis shoes). We went with Gastineau Guiding and they provided a day pack with water, a snack, and a rain poncho and our guide, Becky, was super. I think if you don't plan on doing any kind of hiking, comfortable walking shoes are all you need.