One way to get through the chart issue.

We use the C-series chartplotter with a Navionics gold chip of the entire Caribbean. The Navionics chart can be taken out and put in safe keeping during an electrical storm (if that's possible to actually do). It can be put into a free program you can download from Raymarine. That gives us an electronic backup of charts for everywhere. If you download the Faguai computer program it will work for 30 days before it shuts down. With a Navionics Caribbean chip and the Navionics Usb reader you can download the Faguai program but not activate it unless everything else fails. Then you've got 30 days.

We purchase paper charts only in large are format only and backup with cruising guides for every area we're going. The cruising guides have always had the close ups of harbor entrances and reef areas. Between the large scale charts and the guides we were covered. If we purchased paper charts for everywhere we'd spend a fortune. As it is the large scale charts and guides are still a small fortune.

You can also order charts from Bluewater and they will forward them to anywhere you want.

Here's a link to a post I made a year ago on this site regarding this stuff. http://cruising.sailboatowners.com/csbb/index.cgi/md/read/id/162634/sbj/we-don-t-use-a-computer-based-chartplotter-anymore/

If you're going to Key West you're probably going to the Western Caribbean. Do some research on where the 'Gulf of Mexico Loop Current' is and stay away (difficult to do). It can make life miserable if you are fighting it. We only went West to East and I even screwed that one up fighting a 3 knot adverse current for 24 hours. The link below is a good explanation of it.

Jon went East to West 3 years ago. Wonder what he did?