You could set up each person, with child thoughts formatted as "YY-MM-DD", [Name], [Destination]. Add the itinerary for that leg of the journey in that thought's notes.
Now create a country for each of the destinations, if they are all within a few days of each other, create a thought for each date formatted as YY-MM-DD.
Now, for each persons itinerary thoughts (the first set of thoughts created), link each to the appropriate destination country and date as jump thoughts, or Child thoughts depending on your preference. Now you can view the country and see and see all people and dates, or click on a date and see all the people and destination, or click on the people for all of their itineraries.
Because you are using context sensitive naming (the commas in the thought name), when you are viewing the parent thought, the same text in the child thoughts are ignored.
Java SE 6