1. Do you really plan to sail to the Caribbean
2. The traffic is not the issue. By staying west of the Gulf Stream
do you intend to coast hop and have safe refuge if required? It seems you plan offshore.
3. The rout you propose is largely upwind unless you get lucky. It is also long.
4. Do plan to use a weather
router such as Chris Parker?
5. Will you have radar
reflector? Is your AIS
6. What type of radio
and other safety gear
will you have? EPIRB
There are other questions but these are my top.
Most people do this in November after hurricane
season. The Salty Dawgs has a nicely organized and well run rally from Hampton, Va. find them on line and in their booth at the Annapolis
sail show. You can pop out of the rally along the way, Florida