Would it be possible for him to go with us on a cruise with permission from his parole officer?

My boyfriend has a felony charge of theft by unlawful taking. He did four months of jail time and is currently on parole, but should be on probation by the time that we plan to travel. He is up to date on fines and compliant with all terms of his parole currently. My family wants to go on a Caribbean Cruise which will make port in foreign locations. Should he discuss this with his lawyer? Will he need the approval of the court/judge as well? He already has his passport, he obtained it before any of this happened. If he gets permission, will there be any Caribbean locations that he cannot enter or will there be any other problems during travel?