I just read this entire thread starting in 2005. My wife and I were cruisers from 1975 till 1984. We started on a 22-foot Westerly in Chicago. With one month of experience and $300, we set headed down river to New Orleans
looking for warmer weather
. We arrive just before Thanksgiving and had no problems finding temporary jobs. After 3 weeks sailed to Florida
. We worked in Key West
for 6 months before moving on to the Bahamas
Although I did not work in the Bahamas
, I did get job offers. My talent was fixing things. Almost anywhere you go you will find people with things - usually broken things. In the Bahamas someone asked if I could fix cars. I said yes, he asked if I would like to stay and fix cars for him. I asked if he owned a garage and he replied "No, but I will start one if you will work for me".
I worked a couple of small jobs in Haiti
, and started a business in Puerto Rico
. In St Croix, my wife worked half-time at a coffee shop while I had full time jobs, first fixing airplanes, then as a technician at the navy's underwater tracking range. We lived on what she made and used my pay to buy a 36-foot Cal
We had plenty of time for sailing on weekends and month long vacations. It was not retirement
but we were not looking for retirement
. We were 25 when we started. We want adventure and not having a lot of money
in the bank made it much more fun.
Once we left the US we never had trouble finding work - under the table in some ports
- and we lived cheap
enough that money
usually was not a big issue.
So my advise is to just leave with what you have and not worry.