Let me first say that I love this site and have spent more hours than I would like to admit gathering lots of great information. I am on my second boat and sail on a small reservoir in Kansas. I also have taken ASA courses and did a bareboat charter in the BVI a couple years ago and am planning another week in April 2013. The cruising bug has bit...HARD. However, I am 38 and have 2 kids so I need to work. I also don't really want to take a sabbatical for a cruise (although I may reconsider this as an option later if my other thought isn't possible).
I am a physician and can potentially change my practice and have 20 weeks off. I am looking to find a situation where I can cruise approx four months of the year and work the rest with a couple weeks of vacation in reserve. I also then could have the boat in charter with a good outfit on the east coast somewhere the rest of the year. That way someone is keeping up on the maintenance and it would help defray the costs. The thoughts of doing the Caribbean 1500 every year and cruising the eastern caribbean are appealing except we would be gone during the holiday season and that is the busiest time of the year in my practice. It would be an easier sell to my colleagues if I was gone January-April when it's not as busy.
Any Caribbean based boat would lose valuable "High" season charter time if I was using it during that time. So I'm not sure that is the best option. I'm thinking that a Florida based boat might be the best option? With the Bahamas nearby and potentially the eastern caribbean if the "thorny path" was taken. Also just cruising the ICW and Florida seems interesting. Another thought would be to have a southern california based boat and cruise Mexico during that time. However I know the baja haha fleet leaves at the end of October so I don't know how feasible it is to go to mexico from california in January. Both the Florida and Socal/Mexico options would leave summer/fall charter revenue streams intact.
I guess I would just love some feedback on this idea or any other ideas that might make sense given this time window Jan-April and the possibility of charter income the rest of the year. Respected charter company information would also be great. I should also mention that I would have to get a loan on the boat so any other information about how that could potentially change plans as far as insurance companies are concerned, etc. would be appreciated.
If you are still reading this I appreciate your persistence on such a long winded post and thank you so much for any ideas or information.