Just a tip . . . Get a copy of jimmy Cornell's world cruising routes. It will give you very concise details on all the possible alternative routes and timing.
As to the trip from s cal
. You have two options: (1) Down the coast inside the high pressure system. Against the wind
for much of the sail S of the equator. Administratively difficult in a couple of the countries (ecuador and Peru
) . (2) outside the high pressure, well offshore
. Great sailing but long trip, can stop at a couple attractive islands - this was our choice for one trip to chile.
Timing . . . Be well north or south of Mexico
season, and don't arrive in chile in the winter. That can be further fine tuned a bit for most favorable winds. But that's the "safety" aspect of the timing.
You could also go thru the canal and down the east coast
but that is against the wing and current
until you got past the bulge of Brazil
. We went Down the east coast
for our first trip to chile. It is nice cruising ground - much better than the west coast
(until you get to Patagonia, which is the best in the world).