Sailing to Cuba...need advice on Government and expenses
I really do not have the answers for you.
But my neckhair went straight up, about your question, if you need a passport or not.
You are entering a different country. You need a passport. WHat do you think US customs would say if you galantly sail into their ports without a passport ( coming from the countries you want to visit )
Get a passport, buy the cruising guide and than prepare the boat. Comes to mind the other sentence in your post. A 27 to 30 feet..... what boat you have ? mine doesnt extend. Its 30 feet long but not 27 ...even if I try real hard. Or do you want to buy a boat for this adventure ?