As you can see from my profile I do not post a great deal but spend a fair amount of time lurking and
learning. I have a similar dream to spend a few years on a Cat and just enjoy life. I would reiterate what other have said about taking the ASA sailing class. I have had several years of
power boating experience but no sailing experience. Just in May I took the ASA 101, 103, 104 and 114 courses at LTD sailing in
Grenada. I can not come even close to stating how highly I would recommend them as instructors. My son and I spent a few days on a
monohull and then a week on a catamaran. Until we sailed on both I did not understand the nuances and 'feel' between the two. I realize that this can cut into your
budget but you mentioned that you were going to hire a
captain for a period of time after
purchasing the boat. This would help in having the
training prior to the
captain working with you allowing you to focus on the particular boat you have bought. Understanding all of the systems on the boat is imperative as you push off the
dock since once you are at sea it is up to you to keep things safe.
Just my 2 cents but as I continue to look forward to the days of exploration I now understand what it is like to be on both types of
boats and that I have a ton to learn.
Edit: since Chris of LTD sailing posted just above me it is easy to find the link. He is great and his instructors are awesome. Getting to sail on Dogsmile is simply a blast