10,000 miles in 9 months on a chartered catamaran

My love of sailing started 45 years ago when, on my 7th birthday, I received permission from my parents to sail across the lake in our Sunfish. That journey across a lake in northern Michigan was only 1.5 miles each way but apparently left an indelible impression in my memory of challenge and success. 

My family later acquired a Hobie Cat and eventually a 26-foot sloop in which we cruised the Great Lakes when I was a teenager. 

At the age of 17, I managed to convince my parents to allow me to take my two best friends and sail to the North Channel in Canada for a week. We had a great adventure that we all look back on fondly to this day.  

After college, my attention turned to the challenges of marriage, starting a career, and raising a family along with my wife. We occasionally chartered sailboats for Caribbean vacations but sailing took a backseat to life's many other challenges. But once my children were all in college and the remaining rungs to climb in my career dwindled, I returned to my roots and formulated another big challenge: Why not sail across an ocean? While this would not necessarily be a big challenge for some people, I had very little bluewater experience. I had been driving a desk for almost 30 years with only very occasional sailing experiences, and those were generally in tame waters.   I'm not sure what originally sparked this tiny flame, but it grew the more I thought about it.  After fanning this tiny flame for a few months, I shared the concept with my wife. She was supportive of my wild hair but I suspect a little skeptical that it would ever come to fruition as I was a long way away from retirement at that point and my employer frowned upon vacations much longer than a week. She also made it clear that she did not share this dream. She has enjoyed sailing in the British Virgin Islands and other places that we have chartered boats over the years, but her apprehension increases logarithmically the further away from land she gets, largely, I suspect, due to her lack of confidence in being able to handle the boat if something were to happen to me.  

The next challenge was to flesh out this idea. How should I go about this? What kind of boat? How much will it cost? It was time to get an education. I started by devouring books of some of the greats: Joshua Slocum's book about his adventures on the Spray; Bernard Moitessier's commune with the sea aboard his ketch, Joshua; and a bit more obscure, Bill Crealock's Vagabonding Under Sail. These all whetted my appetite and led to reading another twenty books on a variety of sailing topics from Heavy Weather Sailing to Jimmy Cornell's World Cruising Routes. 

By nature, I am quite conservative and risk-averse. So, as my idea gradually took shape I realized I should probably find some way to get some bluewater experience. I happened to be reading a book by John Kretschmer and it made a reference to his offshore training excursions. I found his webpage and discovered his ...