Need to learn, need a boat, let's get started

[bacougle]

Hi all (hope I'm in the write forum, if not let me know),

After spending the last 10 years travelling half the world by motorbike it’s time to look at sailing it (although first boat doesn't need to be Blue Water).


So where to start? I have been reviewing a lot of forums on here the last weeks and thought maybe I could have more focus if I asked for directions.

I am a 40 year old, reasonably fit with 8 sailing race experience as weight and various touches of rope and hauling of sails in NZ. My girlfriend is 35, fit with strong abilities cooking and in nutrition, but no experience in sailing. We are looking to primarily live on a boat with the odd move to nearby ports in the Caribbean and around the Northern coast of South America and with more experience venture to the Galapagos Islands. But really are open to anywhere in the world that boast lower cost living.
At the moment we live in Argentina Dec to May and 6 months or more in Calgary, Canada during their summer so I can work (I'm Canadian, but Calgary means there is very little sailing culture).
Recommendations please…
Gaining experience:
I think an intro course would be good. I have found no requirements about licenses in the Caribbean or South America, but not sure about this. Cheapest way to do courses?
Working or sailing with others on a boat is definitely an option as the both of us have very flexible schedules. Any recommendations on where in the world it’s easy to find these opportunities?
Boat:
Links and recommendations of boats between 30’ and 40’ for $50,000 USD would be great. We would love a Catamaran for the extra space, and can push the budget to $100,000. I would be adventurous enough to buy a boat anywhere in the Americans and take it to a destination of our choice after living in that place long enough to get the confidence to handle her.
Thanks to all for making these forums great and I look forward to hearing some responses.
Brad