We have sailed the exact route
you are proposing and had a great time.
Having experienced the Windwards and Leewards as well as the Greater Antilles, we now just go to Cuba as there is so much there to see and do and such wonderful people and so close to Florida
For the most part you can day hop the route
. The exceptions are the Mona and Windward Passages (more than a day hop) and I dont know that you would want to day hop Haiti
As for Cuba you must enter at either Santiago de Cuba (south coast) or Puerto Vita (north coast).
Do not consider for a moment bribing an official as that can land you in jail if you bribe the wrong person. And anyway, it is not necessary to bribe them over entry stamps as passports are never stamped not for any national unless you request a stamp. Their standard procedure is to place a loose card in your passport that they take back when you depart. All Cuban Ports
of Entry do this as they know some folks have issue with stamps.
From Varadero or Havana make for West Palm Beach as this is the easiest place to check in as Customs
and Immigration are walking distance from the dinghy dock
and the procedure is hassle free (assuming you are not American in a US Flagged vessel). Regardless of your nationality you must not bring cigars, rum
or anything Cuban into the US.
As for currency, it really doesnt matter which currency you have, all mainstream currencies can be exchanged at a CADECA for Cuban Convertible Peso. Euros will be fine.
There is a new Cruising Guide to Cuba by Capt. Cheryl Barr 2013. The first two chapters are filled with information pertinent to preparing for a voyage to Cuba, routes, check in procedures etc.