It's good to have dreams and while I'm not really in much of a position to answer your questions, I will throw a couple of things out there:
- I wouldn't assume that you'll be slowing down once in your mid 40's
- The slip fees, etc. in different parts of the world may be much different in 20 years than they are now.
- Whether you remain a bachelor or not, solo long distance voyages are inherently much more risky than having another capable person or two along for the ride