I do it.
Montana is my summer base for 4 months, then I roam the planet for the other 8 months. Typically its 2 months in Italy riding my motorbike all over southern Europe, 3 months or so in Asia (mostly Vietnam), and 3 months in Africa, Middle East, etc. I average around 30 countries a year.
You can do it on the cheap if you put some effort into it. $2K a month is pretty easy. I spend quite a bit more than that because the airline tickets really add up and I usually pop for 4 star hotels.
You may or may not get lonely depending on your personality and your past. There's only one way to find out
