While clockwise would be the logical way to circumnavigate South America
1) You're either going to beat against the Southern Equatorial from the Winward Islands until you make the corner around Brazil
(Recife), OR pickup the Equatorial Counter and sail to Africa
, coming back on the Southern Equatorial
2) The Southern Ocean is unforgiving.
3) You will be fighting the South Atlantic, South Pacific
and Antarctic Circumpolar Currents rounding Cape Horn from Atlantic to Pacific.
If I recall
the straight is where Slocum got beat back several times over a month trying to get into the Pacific.
4) That is a long stretch of remote
land in both Argentina