The first problem with your plan I see is most countries only allow a 90-day stay as a tourist.

For most European countries you'll need a longer-stay visa. Look up Schengen. Also see threads on this on the Europe board.

For many of the places you are planning to go HI Hostels would be a good alternative to renting a house. http://www.hihostels.com/
Many of them have private rooms as well as the dorm rooms.
They all have some type of kitchen with food storage including refrigerator.
Are you a US citizen?

>>For many of the places you are planning to go HI Hostels would be a good alternative to renting a house.

Many of them have private rooms as well as the dorm rooms.
They all have some type of kitchen with food storage including refrigerator.<< . . .

. . . And almost ALL of them have restrictions on how long you can stay -- often as little as 7 days. So hostels are only an option for the short periods between longer stays.

Assuming you are American/Canadian, you can't stay in Shengen more than 90 days in any 6 months. That isn't 90 days per country -- that is for ALL of Schengen (Basically all of Western and some of central Europe). Otherwise you have to jump through some serious hoops to get a long stay visa.

You can stay 6 months in the UK - generally an expensive destination.

Not sure about Caribbean countries - you'd have to check each one's immigration rules. And some may have the same rules as their 'parent country' i.e. Aruba/Netherlands

Yes, definitely look into the length of stay limits for the different places you are going - it will be important in choosing where you go and how long you stay. That said, I do know people who have done this and had a blast. In one case, the couple actually sold their house and and then set aside money to buy into a retirement-senior living complex at a later date - they are using the other money from the sale of their house for rent money in the different places where they lived - plus their income from their regular retirement accounts. They are still nomads at this point and it is working well.

I think if you are willing to move often it can work. But you'd need to include countries outside Europe/Schengen countries anyway. Like 3 months Italy, 3 months Brazil or Argentina, 3 months Jamaica or Mexico, etc.

There was an article about a couple that does this - maybe in the New York Times from this summer. It was interesting to read all their preparations and research into how long they could stay in each area. Sorry I can't point you to it - but maybe google the topic...

found it - it was the WSJ. Please notice they have pretty significant income to do this (I'm not saying you don't - but this wouldn't be for everyone!)

http://online.wsj.com/article/SB10000872396390443720204578004131575356160.html

Here is their blog...

http://homefreeadventures.com/

That's a very interesting article, illnative. Sounds interesting, but don't know that I could do that myself.

>>For many of the places you are planning to go HI Hostels would be a good alternative to renting a house.

Many of them have private rooms as well as the dorm rooms.
They all have some type of kitchen with food storage including refrigerator.<< . . .

. . . And almost ALL of them have restrictions on how long you can stay -- often as little as 7 days. So hostels are only an option for the short periods between longer stays.

Forget the time restrictions, I can't imagine staying in a hostel for more than a week, let alone months!!

Thank you all for your input.
I have travelled for business and pleasure for over 40 different countries (to be fair, included Hong Kong, Macau in the figure) but never heard of "Shengen" before.
It tells you that it is never too late to leran something.

I will keep your suggestions in mind and have to keep studying.

Life is short, bt there are a lots of places to see.