On a sailboat touring the world. My second choice would be on a large (1000 acre+) farm right here in Tennessee.
My dream is to have an airship to travel the world. Modern airships can lift 66 tonnes with precision. One could cruise the world flying sightseers, surveying and heavy lifting jobs too.
Buy a small studio condo in your home town/city to use for storage and a permanent address. Buy a motor-home to travel all over the USA and Canada. Laptop for trading from Wi-Fi hot spots or Starbucks.
I've visited Costa Rica more than once, it's a beautiful with friendly people but they have no food culture whatsoever. For me as a food lover this was a big disappointment. I don't think I could there for long without the unavailability of great food getting on my nerves. Maybe it's different in a American expat community, where they import a lot of specialties, that aren't available anywhere else.
Don't they have Mexican food? I don't know about you, but I could eat burritos and green chili three times a day!