Paul, I have no clue about the top row of chips but I can ID some from the bottom one.
$1 Royal Star sails from Port of Miami. Current chip.
$1 Discovery Cruise Lines. Haven't sailed for some time, but it sails from Port Everglades to Freeport, Grand Bahamas daily.
$1 Princess Casino used in St. Maarten & in another Caribbean casino operated by the same group. The island will come to me sometime tomorrow. Tune in.
Sorry I could't be of anymore help.