What do you enjoy doing? Casual or more formal? What types of hotels do you prefer to use?

Definitely avoid the week the week including the 3rd Monday in February as most ships will be crowded (and usually those cruises are more expensive, if not already completely booked).

Is there a reason you isolate yourself to cruises from Florida? Will you already be in Florida? Otherwise I second the suggestion to cruise out of San Juan instead of Florida. More choices of islands, guaranteed warm start to the cruise (unlike February in Florida).