Go for it!
I don't know why people tend to over complicate everything now -a-days. Sailing is not all that difficult. Now sailing the American cup is one thing, but getting from point A to point B a person of average intelligence with reasonable motor skills is more than capable. I have sailed the islands, the Chesapeake Bay, New Jersey coast, Florida Intercoastal all without any certificates or fancy schooling. My equipment was not the "trick of the week" Just basic and able. My boats were sound and relatively inexpensive, No yacht clubs, no racing fraternity, just the enjoyment of sailing. I have friends in their 70's and 80's that are very capable sailors and sail often. I know they could teach a few younger skippers a thing or two. So just get out there in a reasonable boat and do it. I will say that I have been in some scary situations due to the increasing amount of crime in the islands, and I am glad I did not have to face it alone. Find a nice marina with people much like yourself regarding interest and income, make friends and cruise. There is nothing better. Thom