Simpler plan - buy a somewhat bigger boat to use locally. Charter for the Caribbean vacation.
Stepping a mast that large can be dangerous and should be left to the folks with the proper resources.
You may want to look at the Magregor 26 or some of the other water ballasted boats out there...
1971 23' Oday Pop Top
You can't steer a boat that isn't moving? Just like a life - P. Lutus