Our 19 footer would handle four people but not much additional
gear. It's heavier than yours and would be a bit harder to handle by one person. You're probably better off with the two canoes. In one of the latest "Sail" magazines (August 2013) was just a snippet of an article about a couple that uses a 19 foot Grumman Cargo Canoe with a square stern for sailing and camping trips. That would handle more
gear because of the additional
interior space in a square stern versus canoe stern. The article is "Our Self-Rigged Sailing Canoe."