Looking for Advice on Living in the Caribbean

[lukeandkristin]

My boyfriend and I are currently on a 2 year sabbatical. We have spent the past 6 months camping, backpacking, hiking, and mountain biking our way through the western US and Canada. We are very accustomed to living in close quarters, braving the elements, and foregoing the “finer” things (such as showers and running water!). We would like to spend the next 6 months livingaboard in the Caribbean. We both have our 101, 103, and 104 ASA certifications, but otherwise do not have much experience on sailboats. My question is how much should we have planned before heading to the Caribbean? Will we be able to find crew positions if that’s the route we choose (either volunteer or paid) in order to gain more experience? Or should we just jump right in and get our own boat and figure it out as we go, so to speak? Are there reasonably priced long term charters/leases available? Or should we plan on buying our own boat and then reselling? Luke is pretty handy (he’s in the construction business and is a licensed plumber), we are 34 and 31, respectively, both athletic, fit, energetic, hard working and eager to learn. If anyone has any advice or knows of any crew positions, it would be much appreciated. Thanks in advance!!
Kristin and Luke