I’m actually not interested in the most libertarian in the sense of smallest government, I want the freest city in America. I put ‘libertarian’ in the title to draw readers. Here are some choices, and evidence. You vote:
1. Vancouver, Washington. No state income tax. Shop in nearby Portland, Oregon, which has no sales tax. Legalized pot. Right to die.
2. Houston. No income tax. No zoning laws (sort of). Free parking and lots of highways (George Will wouldn’t be herded into mass transit here.) Yes, somewhat religious, but refreshingly hypocritical on social issues (more strip clubs than “liberal” Boston.)
3. LA/San Francisco. Horrible on economic freedom, but lots of room to explore any lifestyle you want. Medical marijuana is effectively open to anyone.
4. NYC. Similar to LA, but NYC is a bit more paternalistic (the Bloomberg effect.)
5. Nashua, NH. All of New Hampshire’s economic freedoms (no income or sales taxes), more social freedom that most free market places (gay marriage.) A short drive to Boston provides some of the freedoms associated with big cities (anonymity, gay bars, etc.)
6. New Orleans. Senator Vitter. Nuff said.
7. Miami Beach. No income tax, casual dress code.
8. Las Vegas. Do I even have to explain?
So which city is actually the freest? I suppose it depends on what you want to do, and which places makes that hard to do. Oddly I left out the Midwest, even though in many ways my home state (Wisconsin) seems freer to me than the East Coast. The more I think about this, the more subjective it seems.