His problems go way beyond having a passport. Seems to me that he has a number of routes all of which have major issues.
1. To Panama and then through the Canal (passport absolutely needed) and then going pretty much to windward to Florida although you get a boost from the currents. Also he would likely want to stop along the way (passport)
2. Around North America (Northwest Passage) - you are in Canadian waters so need a passport. Even with global warming, the ice here is highly unpredictable.
3. Around South America (Cape Horn) - no passport as long as you don't land in the 20 or so countries you will be passing; Cape Horn is a major challenge.
4. Going westward around the world - no passport, if he went around Africa and did not do the Suez Canal and the easiest passage but it is probably 15,000 miles at least and would take a very long time.
I am sure he is a very nice guy but he REALLY does not understand this stuff at all.
Heading back to Lake Ontario for this summer. Relatively few stops along the way from Grenada. Martinique, Guadeloupe, St. Martin (must have something to do with the French food), then Bermuda, New England and up the Hudson/Erie Canal. We were going to go via Newfoundland and Labrador but June remembered that one of the kids is getting married this summer - details, details!