on sailing around the world.....
I too had the dream in college. I bought my first boat - 3' draft, 24 foot alden sloop for $3K and sailed the snot out it, working on it to learn the systems, on a lake in Dallas. I learned a lot. I sold that boat and began moving progressively up in size and into the ocean - building more experience. After 10 years of planning and practicing offshore in progressively worse weather - some by design, others by freak accident, i acquired a beat up Morgan 41 - spent 4 months working and outfitting her and off I went to Puerto Rico.
Most of the trip was magical - dolphins surrounding and playing with my boat in the middle of nowhere near sunset, etc. The parts that weren't were the days of 16 foot, short period seas and losing my steering in the midst of them.The experiences learned prior to this event saved my life and my boat - I knew what to do (as my butt severely puckered and my adreline went through the roof), how to control my panic as a single hander and how to rapidly assess my situation and get my boat out of a beam sea broaching situation and back to an island 9 hours away to affect repairs without additional help. I knew this because I had experienced progressively similiar situations in the prior 10 years; from practice and other things randomly breaking on other boats. I had worked on my boat and knew it inside and out and I had spent a lot of "what-if this were to happen to me, what would I do" time as I laid in bed at night.
Because of these things, my near disaster became nothing more than a really crappy day on an otherwise difficult, but great run down the thorny path.
I now live and work in Puerto Rico and play in the waters I love so much. Never made it around the world, but I did make it to the part of the world I truly enjoy the most - the US/British/Spanish Virgin Islands.
It would not have been possible without the proper preparation. Nobody is trying to rain on your parade - just really help you understand the importance of knowing what raingear to wear when to join your parade. Rookies aren't often allowed in race cars for a reason - they tend to break expensive things and sometimes die in the process. Same with boats crossing oceans.
Keep your dreams alive!!! Live them and enjoy them, but gain the skill and confidence necessary to do it right. The life you save may be yours and the loved ones with you.
Best of luck realizing your dreams - plan it, properly prepare for it, then do it!