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wrote:

Here is a hypothetical question:

If somebody on a sailboat did NOT want to be found and had a 36 hour
head start leaving someplace like say the N. Florida Gulf coast, how
difficult would it be to find him.

This depends entirely on who is looking. If the CG wants to find you,
they will track you from the beginning of the trip and the color of
the boat or whatever won't make any difference.

If the person can avoid being a person of interest to homeland
security or the CG so that neither of them has an interest in looking
for the person, then there's no need to take any special precautions
..
I assume the sailor not wanting to
be found could take some measures such as painting his boat a grey
color to match the water or even paint his sails, not use lights at
night, etc. What else can you think of to minimize his chances of
being found.

Probably the best thing to do would be to set off as if it was an
ordinary trip, say from Texas to Pensacola on the ICW, and file a
float plan with someone to that effect. Tell them if you don't turn
up in Pensacola in 2 weeks, to start to look. Then go the other
direction.

How difficult would it be in this case for conventional SAR to find
him? Remember, every 36 hours, the necesary search area quadruples

Why is the SAR looking for him?

until after a few days it covers the entire Gulf of Mexico and its
shoreline.
I think it might be possible for such a sailor to elude being found for
a long time.

grandma Rosalie