Join Date: Jul 2002
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Place to Place
You make it sound like you wish to fund your cruising by occasionally working vs. looking for a new, semi-permanent setting in which to locally sail. How easy/hard it will be to find work won''t be a function of your trade, which is readily marketable IME. Domestically, it will be driven by where you stop and how long you stick around - e.g. getting a job in season in the Ft. Lauderdale area would be relatively easy, while finding work in Beaufort, S.C. or N.C. (two common yachtie stops) might be much harder. Another option is to stop at common ''prep'' and staging areas where cruisers accummulate prior to heading out, or where they come to lick their wounds and need boat repairs done. Examples of this might be Lake Worth or San Diego (before boats head for the islands or Mexico, respectively, and where there are large gatherings of transient boats that are relatively easily accessed by you. You''ll have to go find the work vs. working for an existing business, where the work finds it.
Outside the U.S., it will be driven by how eager the island nation or country is to provide work permits to non-residents (usually they are not), how comfortable you are in working quietly ''under the table'' (with a developing world prison & legal system as a possible consequence of being found out), and/or whether your track takes you into an offshore U.S. commonwealth or territory where you have work rights. Examples of the latter are the U.S. Trust Territories and American Samoa in the South Pacific and Puerto Rico and the USVI in the Caribbean. A great non-U.S. place to find work in the Caribbean is Grand Cayman, where there are hundreds of open positions (many of them boating related) and very few excess workers. Employers pay for the cost of the 6-week work permitting process and even offer retirement plans & health care for non-residents.
Perhaps you could refine your question a bit (where are you headed, how long are your stops, in or outside the U.S.?) to get more helpful answers.