We are also planning a a 5 month trip in Oct. leaving from the Chesapeake down East Coast, to the Bahamas then back to Florida which we will call our new home. The cost of cruising is a tough question. We''ve been researching it (reading various books and articles on Sailnet) for over a year and think that it will cost about $700-$900 month. We plan to anchor most of the time with occassional marina stays. We do plan to eat out occassionally, and we will be visiting some bars!
Best of luck to you and perhaps we''ll see you out there!