It is all about the (achievable) dream(s)

I still meet time to time  few folks who "dream" about sailing the world. 

Cruising. 

Sounds an expensive, unreachable, dream.

It is not. (I mean, hopefully, I will prove them wrong, and prove me right).

True, it is complicated. But it became an attainable adventure. (tm)

Requires a lot of commitments, years of it - if you are not rich or have obligations, but with the right amount of time and focus, certainly achievable.

Back on the mooring

First, owning a sailboat is not exclusively reserved to the wealthy anymore. Nowadays, following the boom of production boats, there are hundreds of boat from the 70-80s that are less expensive than a new car, waiting for an unconscious dreamer.

True, you might need to move to an area where you will be able to moor or store your boat, and that alone require some planning.

But, Well, if you want to go cruising, maybe start to live by the sea.

Appreciating the dodger - for a (rare) rain

You will have to be handy, or learn to be. Slowly, with lots of mistakes, I am making my way to be mostly autonomous. I learned with Lego as a kid, and that would have been the closest from any handy work I will have been until those last couple of years.
Now I can build a dodger, change the fuel system, do the maintenance of my diesel engine (and not only the oil, please), and so on, so on.

https://www.morganscloud.com/

Last, but not least, the online community is super helpful and huge.
There are books on everything, YouTube videos on everything.
Seminars, Training, Websites.
So much content to drive you that it might be overwhelming.

All you need is Time.
Time to spare and spend money.
Time to work on the boat.
Time to sail the boat.
Time to cruise.

And time is the real currency for dreams.