As a boat carpenter, some work along the
line must surely come his way but it likely means staying in one place long enough to let the word of mouth get around and work to come in.
There is not enough information to provide sage counsel, nor should you bare your finances on the web, but there are some guidelines that come in handy. Let''s assume that you have some retirement but are planning just for the cruising kitty. Most financial planners will tell you that you should have 3-6 months of cash reserve in addition to the money you plan to live on in a normal non-retirement situation. This rule of thumb can also be applied to cruising.
If you have to work an extra few months to pile up the 3-6 reserve, that is after you''ve set aside the actual kitty, do so. Even the cost of shipping needed parts from the states can be an unwelcome and often unplanned for surprise. What you make while cruising can then be real quality of life money. On the other hand, if you take the notion to the extreme, you may never leave port. Working in the islands you can also face work permit issues and of course there is the normal "grease local palms" costs that crop up.
As a sailor buddy once said, "we spend two things in life, time and money...and you can always check on your bank balance."