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Hi guys - been lurking here for a while and I figured I'd start a thread to (hopefully) tap into the collective wisdom of this forum   

I’m turning 45 in a few months and have long since come to the realization that we MUST make the best use of our opportunities as our lives is but a blink of the eye. Thus, by the end of next year, the wife and I plan to pack life in as we know it and start traveling full-time – while we’re (mostly) still of sound body and mind. 

I know what you’re thinking. What crazy hippy crap is this?!!
I’ll add more later..

Ditto 

Good man, also going to be doing the same thing.

On the financial side - would look at other countries tax systems. For me, the UK system has a lot of advantages. Will you be keeping the properties or converting into shares/REITs? Would be looking at fixing some of that income (if staying in SA) into euro's/dollars through oversea's reits.

This is really going to be interesting tax wise. You will have to do stacks of juggling here trying to keep your tax residency in SA. Gets very complicated in this case.

In the first place EU countries.

You’re automatically resident if either:

1.You spent 183 or more days in the country in the tax year
2.Your only home was in that country - you must have owned, rented or lived in it for at least 91 days in total - and you spent at least 30 days there in the tax year.

So you would have to relocate to a different country every 90 days to escape being tax resident.

If you happen to get this right then you have a further problem. SA will regard you as non resident after 183 days absence and all your properties will be regarded as a "deemed" sold at the valuation on the day you left and CGT will be payable.
Good news is that you have 5 years to pay it in yearly increments. With interest though.

More later. Beer time.

Nope. I'm in Portugal. We have great wine here too.

Here is why you should duck.

I’m turning 45 in a few months and have long since come to the realization that we MUST make the best use of our opportunities as our lives is but a blink of the eye. Thus, by the end of next year, the wife and I plan to pack life in as we know it and start traveling full-time – while we’re (mostly) still of sound body and mind. 

I know what you’re thinking. What crazy hippy crap is this?!!
I’ll add more later..

Actually I'm thinking me too! This is exactly what I plan to be doing in a few years time. I'm sitting typing this in Lisbon, where my wife and I have spent the last few days walking and cycling all around the city. Wonderfully, the biggest worry we've had is that we don't slip on the polished mosaic pavement. A pleasant change from whether we'll be mugged in the 300m between the gym and our apartment, or if the lights will stay on for all of next month (9 days without power in the last 30).

There's a lot to see in this world, and I hope to explore as much as possible before I need plastic hips and blood pressure medicine!

Though I must mention one interesting thing we noticed in the local travel agencies. They have cheap offers for pretty much all of Europe and the west, but their most exotic and expensive trip is a combo trip to Kruger park and Mozambique! Everyone we speak to is in awe that we've been to those places. The pot of gold always seems to be at the opposite end of the rainbow.

I love the topic...

excerpt from a book ' the gypsy in me'
Solo travel has a peculiar power for those of us who are suited to it. Along with the discovery of one's own true nature and the opportunities to express it comes a corresponding freedom to think thoughts that may be considered odd, threatening, even reprehensible and lunatic, by ones familiar acquaintances. It is perfectly natural that prophets should come out the wilderness bearing revelations, but all prophets are not created equal. Some are giants, some are mediocre, some are of piddling stature, and some are nuts. The difficulty is that neither they nor those that receive there proclamations can really tell untill much later.

Mine is not pure asceticism of a single-handed yachtsman or a Saint-Exupery.There is no lack of people in my journeys, and they are my principal interest. Nor am I a dispassionate voyeur peering into other peoples lives. Strong connections are formed rapidly, and they nourish me. What distinguishes them from my relationships with friends and family at home is the absence of those expectations which I find burdensome and restrictive, demanding that I behave in certain predictable ways. These emotionable transactions trade too heavily on guilt and obligation for my taste. When I travel alone, I experience a sense of freedom that occasionally comes close to ecstasy.

The physical freedom is an important element - the ability to stay or go as one pleases, to follow whatever the inner voice suggests, is a rare luxury in most lives, and there must be many who have never allowed themselves to experience that inner-directedness -- the compass in the heart. More valuable to me even than that is the freedom to be whoever and whatever you feel yourself to be rather than having to conform to the patterns that others are accustomed to expect. "