Originally Posted by Scott&Rosie
What is the minumum size boat I should entertain for extended cruising in the caribbean with a max crew of five.
It is not clear what size boats you have sailed on Lake's, so I run the risk of suggesting something you are already quite familiar with. With that in mind I offer 3 basic book suggestions; all 3 can be bought used cheap - Amazon, Abe's Books, etc...:
1. How to Buy the Best Sailboat by Chuck Gustafson
2. Multihull Voyaging by Thomas Firth Jones
3.The Case for the Cruising Trimaran by Jim Brown
All three are a conservative approach to sailboat ownership and cruising. Personally I would not want to be on a sailboat for an extended period of time with others on less than about 37' sailboat. You should be able to get two staterooms in something that size and then there are the salon cushions when added folks are aboard.
But I see many happy people on much much smaller sailboats for years, very satisfied folks. Maybe you need to spend some time chartering at least once, before making a purchase. Experience is a good teacher.