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Have you considered using an offshore, Coast Guard licensed (or ASA et al) sailing instructor to help you reposition your boat. It would be an excellent opportunity to gain valuable experience with well organized, informative pre-departure studies, planning and boat preparations. You should expect to build confidence during the journey and have an added license after you complete your test.
Adding a new license could help lower your insurance premiums, improve your sailing abilities and boost your self confidence.
When its "my turn" to venture offshore for the first time, I plan to do it this way.