I set it up so each region had its own hashtag, but with a limit of 5 it drastically reduces the effectiveness of the group...as in not worth doing.
Since there can be up to 5 for each topic, I don't understand why you'd need more than that. I understand that someone may go to Mexico, Bahamas, etc, but would they need their entire itinerary (hashtags) on one topic? If I'm reading your information correctly, each person/topic would only be in one region at a time. Seems that one hashtag would do that. I could see having 2 or 3 if they're moving from region to region within a short time. If it's not so much which people, but which regions, you could have a topic for each region that folks would add to when they get there.