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Depends on objective, food or sights. Factoring in both I would say in no particular order.
1. US
2. Italy
3. Greece
4. Argentina
Those are pretty easy, lots of sights and great food. Last one tough. It must be somewhere in Asia but I don't like going to trashy places or where I see lots of suffering (cant enjoy anything if thats present). That rules out all of asia but Singapore, Japan and Hong Kong, maybe Thailand (but large parts of it are pretty backwards). If I was basing it on food #5 would be Singapore and if on sightseeing then it would be Japan. If I was feeling adventerous and willing to sacrifice a little of both then I would go for Thailand.
From the capitals of each of those countries, you can make short day trips into at least three other countries, giving you a total of at least 20 countries for your five trips. And you'll get four continents. And, you'll get to see something of the world beside big modern western-style cities and rich people in store-bought designer clothes driving air conditioned automobiles.
Not in order...
USA, Brazil, Italy, Thailand, Japan.
Haven't visited Brazil and Italy yet.
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