Collecting flags by traveling to as many countries as possible is probably just as senseless as collecting stamps. These days though, when no one asks "how was Thailand" out of interest in the country - nothing new there - but out of politeness, it does however bring you some leverage in a bar chat if you get to tell people that you've already been to, let's say, 50 countries.
That would mean that one had been to about every forth country in the world.
(United Nations has recognized 192 countries. In addition to that there are a few countries which have proclaimed themselves independent, but which have yet to be recognized by the international community.) To most people at least that's more interesting then having stamps from 50 different countries, unless of course all the those countries were ruled by blond Amazonian Xena - warriors who in their free time like to flash their grape fruit sized tits to unassuming dolphins, making Paris Hilton gulp in awe of their imagination.
So if you don't have a billion dollars and a private jet, here's what you can do to increase your country count, and see a bit of the world in the process, while staying in budget.
1. Travel Europe, but plan well. With the strong euro Western Europe is probably dearer than ever. Instead, book a no frills flight to Split, Croatia (www.airberlin.com, www.easyjet.com), or Belgrade, Serbia (www.germanwings.com) and tour the Balkans. All the former Yogoslavic countries are rather small, so getting around does not take much time. I spent three weeks traveling Serbia, Bosnia, Croatia and Slovenia. Ad two weeks to that and see Montenegro and Macedonia, from where you can easily make it to Albania. That's seven countries in five weeks. Doable, if a wee bit rushed.
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2. Hop on an overland truck in Africa. As Africa tends to be awfully expensive, overland trucks are a cheap way to collect a few flags. Taking a truck tour usually means lodging at campsites and participating in cooking and shopping food. This crazy-ass tour for example at African Trails takes you to 29 countries such as Burkina Faso and Malawi in 43 weeks and costs around 7000 euros, including meals (cooked by you or your fellow travelers) and accommondation. There are shorter tours as well of course. And if you hit Kenya in the fall you can witness the wildebeest migration which is so much more hip than any lion will ever be.
3. Skip India! You'll only get stuck. For monetary reasons skip Oz and US.
4. Central America is packed with small countries. Choose them instead of Brazil.
5. Travel to any country that is in the verge of splitting up and then decide that if you've been to the territory it counts as a country even if it wasn't at the time of visit. A Soviet Union trip added Georgia, Armenia and Azerbaidzan to my country count in 1991, a few years after the trip.