Good advice on the counterclockwise route and the sun factor. Having taken this trip, or variations thereof, in the past we know that wind and weather plays a big part. What with the recent high temps and resulting afternoon storms, I recently added WxWorx XM Weather to our boat. This is a very handy tool, in fact, it may be as valuable to the cruiser as a GPS. Based on Baron's weather service, the satellite platform provides weather overlays on your laptop and has filters to show wind, waves, doppler, bouy data, and some tropical information like hurricane tracking and water temp. When combined with GPS, the software tracks your vessel and projects surrounding weather. It can be zoomed from nationwide down to city level. Check out their web site
http://www.wxworx.com/
We are now equipped with 2 VHF's, SSB, 3 GPS, Cellular Repeater, WxWorx, copious charts and plotting tools, computer and hopefully some good common sense. Our departure has been delayed until tomorrow due to incoming weather, so, today I'll fuel her up, wash her down and start on a couple of "honey do's" Miss Donna has assigned to me over the course of the trip.
Terry