It's been a few years, but before we had kids, we did Upper Dewey Lake. It was a pretty steep climb of 3000 feet but amazing. We ran into about four other people while on the trail. One of our best memories of the cruise... walking off the ship while everyone else was sleeping it off and starting a hike a few hundred yards from the pier. When we go back to Alaska on a cruise we won't be able to do it again due to two young hikers but one day we will do it again. National Geographic has a map of the area. Search for "National Geographic Chilkoot Trail"