The way to organise a RTW within your budget and timescale, is to chat to others that have done it.
I'll start with a little humble advice (though I don't like giving too much when it's someone elses itinery - and not mine)....
Star Alliance means nothing, as far as cost is concerned. It's still very expensive - and all it offers is a few agreements between a few long haul airlines.
It is so often nowadays, cheaper to spend a day or two going square eyed in front of the monitor - and getting seperate flights from one country to another.
For example.... Manchester to Southern Turkey is around 3,000 miles. It can be done for €40 one way. Then from Southern Turkey (Dalaman) to New Delhi is on offer in October (as is the Manchester fare) for under US$100. So there you are.... Almost half way round the world for under $200.... Easy, with a little patience. It's fun to explore the options too.
[ Edit: Edited on 09-May-2009, at 12:25 by Redpaddy ]
It is possible on the Continent based one world fare to get an itinerary that takes in 5 or 6 continents, but it is about the most expensive rtw ticket available especially when purchased from North America. The Kenya bit will be nigh on impossible on a rtw ticket without doing a huge section overland or buying a seperate ticket from South Africa to Nairobi which would cost a fortune.
For your sort of trip it'd probably work out best if you started from the US rather than Canada if it doesn't cost too much to get from somewhere like Toronto to New York. You could get the itinerary to go North America - South America - Australia/Pacific - Asia - Africa - Europe - North America. It'd get you a lot of frequent flyer miles and also allow you to see a lot of the world. It would not be a cheap rtw ticket but compared to buying all sector fares you'd be getting a bargain. If it is possible to get from Toronto to Los Angeles relatively cheaply i.e. under about $300USD I have sometimes been able to book US citizens a cheaper RTW ticket which had longer than 12 month validity. It is not usually possible to get any airline ticket to have a validity of longer than 12 months. The bad part about doing it the way I have done for people is that it limits your ability to have many included flights in the Australasia/Pacific region (which within Australia can be got pretty cheaply if you book in advance).
A sample itinerary which could be expanded better if you were to get to Los Angeles cheaply would be LA - Nadi(Fiji) - Sydney or Melbourne. Then a rtw ticket starts by going Sydney - Bangkok - Tokyo - Beijing - Hong Kong - Johannesburg overland to Livingstone - Johannesburg - London (base your European travel from here) - Madrid - Sao Paulo - Lima - Mexico City - New York - Toronto - Los Angeles - Sydney. With this last section the Los Angeles and Sydney sectors are to make it a valid rtw ticket and then you would just fail to turn up for those flights seeing you'd have got back home with the stop in Toronto. I'm pretty sure this would all just sneak on to the 6 continent rtw ticket but some of the flights may only go once or twice a week so it would be a matter of playing with the dates. To get that itinerary it would require all flights to be direct which may only happen once a week.
If you began in North America on the RTW ticket it'd probably require going Toronto - Los Angeles - (Europe, South America or Australia depending on which direction you want to travel).
I wouldn't expect to get out of it cheaply with the sort of itinerary I have mentioned but you would have one hell of a great trip!
Basically you have no hope of getting to South America and not much in the way of Africa on the Star Alliance fare and no way to get it under 32,000 miles. It's a very basic rtw itinerary that doesn't have many ups and downs in the itinerary that is that small. Anything that gets to South America goes in to the maximum mileage limits and I am not aware of any flights on the Star Alliance network that go there (that's not to say they don't have one or two isolated ones which couldn't be incorporated in to a rtw ticket).
[ Edit: Edited on 13-May-2009, at 03:26 by aharrold45 ]
Lufthansa (S/A) fly from Frankfurt to Sao Paulo, Brazil.