Sounds like you have some pretty ambitious plans and working south from B.C. to Mexico is a good and safe way to build your offshore confidence. Now to answer your budget question; in my opinion there are three brackets basically separated by $1,200 increments. You didn't say how large your boat is, but for a cruising couple on a 35-40 foot boat here is the range you should expect:
Economy: plan on about $1,200 per month including food, fuel and supplies. This means always anchoring, no dockage fees, eating aboard, free entertainment options like hiking, fishing etc. instead of movies and paid excursions ashore, and lastly do it yourself maintenance.
Intermediate: plan on about $2,400 per month including food fuel and supplies. This means mostly anchoring, but occasional dockage, limited eating ashore, limited paid entertainment and occasional use of day workers for maintenance items.
Luxury: plan on about $3,600 per month including food, fuel and supplies. This means anchoring still, but dockage when desired and an occasional hotel room to get "off" the boat, occasional excursions with a rental car and paid entertainment, use of day workers for minor maintenance and skilled workers when necessary for maintenance.
Note: the figures above do not include medical care, travel home and the emergency kitty. I strongly recommend that you invest in an international medical insurance policy and there are several companies that specialize in this kind of coverage for sailors and the policies even include medical evacuation. Famous cruising sailors Lin and Larry Pardey published the following article on medical insurance for sailors LandLPardey Tips that recommends one carrier. The deductibles ($250-$5,000) will determine the cost and a policy with a $5,000 deductible will run about $2,700 annually depending on your age and you need to have the full deductible on board.
The figures above also do not include the cost of travel home so you should also have cash set aside for at least one trip home for each person for each year you expect to be gone.
Lastly, you need an emergency kitty for anything major that goes wrong and in my opinion this should be at least $3,000.
So, the answer is pick your monthly cruising plan above $1,200 | $2,400 | $3,600 and then add $2,700 medical insurance for each person (assuming 2 people = $5,400) and then add a cash kitty of around $10,000 to cover your medical deductible, travel home and emergency fund. So for one year of Economy Plan cruising you need $14,400 for monthly expenses + $5,400 for medical policies + $10,000 cash kitty, or $29,800. For one year of Luxury Plan cruising you need $43,200 for monthly expenses + $5,400 for medical policies + $10,000 cash kitty, or $58,600.
These are safe guidelines and of course they can be adjusted somewhat depending on your lifestyle, but I wouldn't plan on much deviation from the economy plan. Hope this helps.
Captain Bob Wellen, Red Sky "