Boats do not represent "freedom."
In comparison to what? Being in a house where the EPA starts to monitor your electric usage, NSA monitoring your internet, and taxman saying you need to pay property tax, which means you don't own the house, you're basically just renting it. Yea, they can tax your income or other assets, but it's a lot harder to try and tax the ocean the boat sits on.
Then of course, there's obviously more freedom of travel, since the gas can stop pumping at any time due to some kind of currency crisis. You don't need gas for a sailboat, although it is useful in many circumstances. Boats also offers many creative ways to get yourself killed, which is obviously a form of freedom from a nanny state.
The fact that you can survive without having to go to a grocery store is also obviously a checkmark for freedom. So yea, a boat is going to be an objective increase in freedom for most people.
If an economic apocalypse occurred, do you think you would be safe on your little boat? You'd set into harbor and find an entirely new sort of harbor master staring at you, surrounded by his little gang of thieves. Depending on how and what you paid him, he might even let you keep your boat.
It depends. Most people that own a 26' - 40' boat are usually more self sufficient in nature (although people owning 200' boats might not be), and aren't just going to turn into Mad Max Beyond Thunderdome when they already have food, water, and shelter themselves. People on land missing many of these things might be more inclined to do so. Yea, piracy would increase, so you're not going to want to just sit out in the middle of the ocean for no reason, you would just identify a safe place to sail to and go there and live right offshore obviously. You would also want to identify and talk to anyone near you and probably form some kind of agreement to not kill each other and probably defend against other people trying to do so.
He wouldn't be safe even in the open sea in case some apocalypse should occur. To survive there you would need something like The Last Ship with a crew of marines to help you. Otherwise it will be a one-way cruise on a lethal mission.
It's not realistic to pretend everyone on the planet with a boat is instantly going to turn into a Somali pirate should an economic catastrophe occur. There's not going to be large ships of inner city, rap music listening people attacking you. 99.99% of those are going to be on land. If all you have is a 30' to 40' boat, chances are that anyone you run into is going to have the same or better. If you have a 100'-200' boat, then yea, someone might eventually get greedy and try to take it.
Why you just don't buy a house in a woods?
You would probably be ok if it's a large distance from any populated area, but maybe it would be miserable there for a long period of time, and maybe the guy in the boat just drove the thing to where things are still normal.
]Alaska, New Zealand...
Why not some place that's already at the bottom of an apocalypse? Maybe it could only go up?
Argentina?
In case you didn't notice, a boat can go to all of those places? lol