Re: Alternatives to buying your own boat
An interesting topic since I find myself in the same exact situation. I've done a lot of sailing in Florida, Bahamas, and the Caribbean both by myself and with others. Single for most of my life, I'm close to retirement.
In anticipation of cruising after I retire, I posted a few inquiries about what other cruisers thought about a single hander and without exception, all replies said don't do it. To tell you the truth, based on my own short duration single handed saling cruises, I would have to agree. The geography is beautiful, the sailing is great, but it gets boring without someone with you, whether that be female or male. It can also be dangerous single handing a boat continuously.
Too bad you're on the opposite side of the US, Andifreed. Who knows? We may have hooked up.