Regarding charts from the Turks to PR
, Maptech has a chart book that covers that entire leg of the route, it was just published last March. I think it is called 10 or something like that. It is excellent for that part of passage and fills a big void.
As mentioned above, the dingy is critical. You must figure a way to store it on the boat. It is your car once at anchor. You will need to secure it on deck when cruising. So convienence of hauling it aboard is critical. I use my spinnaker halyard and a winch to raise it up. The dingy engine and gas tanks store on the rail and in the cockpit. You will be raising and dropping the dingy every time you stop. So get that system down. Also, down island, dingy engines become targets of opportunity for the locals so be prepared to secure it when away from the boat and at night.
The Bluewater Bookstore in Ft. Lauderdale is an excellent place to acquire charts, guide books, etc. Go there on the way south and spend a day acquiring stuff. You will not regret it as you go down island. Pick up your courtesy flags there as well.
When you get to Puerto Rico, you might also want to stop at Salinas just past Ponce. Its a good harbor and has a great mangrove hole nearby for weather avoidance.
Get your weather from Chris, you will need an SSB radio. His advice is good tactical info. Get your strategic planning from Van Zant. His sailing advice is getting dated but his basic approach is excellent and timeless.
The first 1200 miles are all nose into the wind. So plan on a lot of fuel consumption. If you don't have a lot of tankage and jerry jugs in the beginning, you will by the end of your trip.
When you get to Georgetown there will be groups of people getting together for making the voyage south. This can work out, if you find compatible folks to sail with. Or it can become a problem. Always be your own captain. Read Van Zant for his strategy and you will do fine.
The chartplotters dont work well South of the Turks because the charts are old. You will sail through land when you get to Luperon, even though it looks like water to you. Trust your eyes as you go south. Van Zant's low tech advice for entering Luperon will work best. Go the southern route across the Turks & Caicos.
Always listen to Chris Parker. Get his book for the frequencies and a lot of great weather related advice. Also check out his web site:
Make sure you can download the NOAA Off Shore weather faxes, you'll need the weather fax hardware and software kit, its about $200. Get it in Ft. Lauderdale. You will need your SSB functional to use it. Parker's book and the weather fax documentation covers the frequencies.
Learn how to listen to the NMN broadcast from the coast guard on the SSB. Check Parker's book for the frequencies.
Make sure you have good anchors and rodes available. I carry 4 anchors, a Delta, a Bruce, a Fortress and a Danforth. My primary rode is all chain on the Delta. I have two rope rodes for the fluke anchors and a combination rope and chain on the Bruce. More is better than less.