I think Tom’s answer in his blog is the best answer.
Additionally, the Heritage Society publishes an annual index of economic freedom. The most recent list of almost 200 countries is at http://www.heritage.org/index/.
But it also occurs to me that liberty is a work in progress and it’s being tried all the time, every where, to different degrees.
If your job was to set the destination year on the time machine, how far back would you set it to go to a culture that thought the earth was a flat surface located in the center of the universe and that any attempt to create a democratic, self-governing political system was absurd and insane.
Once there, whenever that was, as you gradually reverse the time dial and return to the present, liberty was incrementally growing (admittedly in fits and spurts and not without setbacks) in virtually every sphere of human society.
We’ve actually arrived at a time and place where individuals freely communicate globally over the internet with such an unprecedented degree of liberty that they can assiduously avoid regressive publications like The New York Times and Salon!
With regard to “world history” and libertarianism, a few examples that come readily to mind as advancements of liberty – the central tenet of libertarianism – Magna Carta and the English Bill of Rights pop up, along with America’s Bill of Rights, the U.S. Constitution and the 13th amendment.