So our plan was to start in Mexico and work our way down through Central America to South America. I neglected to include the Caribbean though. So I'm wondering what the best way to fit that into our plans would be. I'm thinking that maybe if we fly from Mexico City to Antigua and then use that as a base to island hop that it might work. Then we'd fly from Antigua to Cancun or something.

Or is there a more logical or cheaper way to do this?

We'd be going to Cuba (we're Canadian), maybe DR, probably not Barbados or Jamaica, and maybe not the Caymans (the rest of the island are probably fair game though). We're not too interested in staying in resorts so I'm told the smaller islands are probably a better fit for us.