"2. What are the newest requirements to legally enter Cuba?"
You need to do some research
here. Its YOUR government
(USA) that has the legal
requirements, not Cuba. Upon entering Cuba you only need to check in and do the required formalities.
"3. What currencies are usable throughout Cuba and if only their currency where in SW FL. Can I exchange my US$ for that currency to take with me?"
Cuba has 2 currencies, Convertable Peso (CUC) and National Peso (CUP). Although have some CUP can be usefull its not required. CUC is all you require. I do not think there is anywhere in the USA to convert your money
. Just convert it once you arrive (yes they take USD).
"4. Do I need an AIS Transponder? I have a brand new Garmin
Chart Plotter with integrated radar
The channel between Cuba and Mexico is a super busy shipping/cruise lane. Having an AIS transponder would be very valuable. Personally I wouldn't go without one.
"5. I am concerned with the Gulf Stream crossing of about 47-50 miles between the western tip of Cuba to the Cancun area. When is the best month, week, day of the week to cross? I look upon that crossing as being equivalent to the SE FL to Bahamas
crossing. Am I correct in my assessment of the dangers to a small boat like mine: commercial
boat traffic as well as the Gulf Stream currents/wind combination? "
I have made this crossing once so I'm not an expert. I have been told that April/May are the best times to attempt it. You need to watch the weather
and wait for the right winds. You also should pay attention to the reefs
on the north side of Cuba. Many boats have been lost
"6. What are the best and reasonably priced marinas in the Cancun/Tulum area? Once I arrive I am planning in locating a slip with shore power
30/50 electricity, water
and pump out facilities. Wi fi and/or Internet
and cell phone
availability would also be nice. I intend to rent a live aboard slip for several months and the explore the area. "
As previously suggested, Marina Paraiso is a good place. Our boat stayed at Oscars for 6 months and we were happy. You will just need to shop around and see. I suggest you do it before you get there as the marinas can fill up in the lagoon
. The ones outside the lagoon
usually don't allow unattended boats during hurricane
season. There are really no pumpouts in Mexico, most boats direct discharge (yes really).