Hello Cuba Bound,
Your choice is good but your timming may be a little off. The trip is well worth the effort but there are several key considerations to keep in mind.
As your boat has been on the hard & I asume that you have been doing some upgrades & refitting I would reccomend that you do some shakedown sailing prior to heading to Cuba. Should experience boat problems while their you will be at their mercy, they will attempt too help however they to are at a disadvantage. As I am sure you are aware of that is not where you want to be should the weather come at you hard & strong. I got caught there several years ago,only because I just couldn't pull my self away an it was starting to get deep into huricane season & finally I had to make a run for Guatemala, & today that is not a place you want to lay up for the season.
One last suggestion if you decide that this is your time to do it you may want to jump over to Beliz first & there you should be able to get some insight as too any problems you may experience from fellow cruisers returning to the states to set out the season. One of the replys you received advising you not to broadcast your intentions as to your plans to sail to Cuba. That individual was 200% correct, The Cuban Government just might be the lesser of your problems.
Good Luck & if you would like too more chat please drop me a line, I will be leaving for Fla in several months to refit my Lady, Whant to guess where my second Port of call will be.?