You may be able to get the insurance, but the question is: can you afford
it??

You have several factors against you, single handing, offshore and your boat
is over 20 years old. All of these are key factors and difficult to over
come with regards to insurance.

They will insure 20+ yo boat but only after a survey and since your going
offshore, they will usually require a detailed rigging and chain plate
inspection. Most likely they will requiire the standing rigging be replaced
since there would be too many unknowns that the rigging inspection can't
verify.

Most will turn you down if they findout your sailing singlehanded.

Offshore will still be expensive but if you over come the other problems, it
is possible to get coverage for offshore, but with some restrictions on
ocean areas of the world.

Note: Now, if you happen to be a military/USCG officer, retired, or
dependent of a military officer, you could qualify for USAA insurance and
they offer a yacht policy without any such restriction, as long as it passes
a marine survey. I've been with them for over 30 years. Good rates, but of
course, I've never had a marine claim..

My opinion and experience, FWIW.

Steve
s/v Good Intentions