Click on the link above to see a Google "My Maps" map of the route broken up into different stages showing projected mileage and dates.
I'm definitly not the first person to travel this route or routes similar to it. In fact there is a yachting route called the "Great Circle Route" or "Great Loop Route" that people do in big boats fairly frequently. A gentleman actually rowed all the way around the eastern US once as well. Follow the links to learn more about trips like this.