[en] The surface circulation of the Caribbean Sea and Gulf of Mexico is studied using 13 years of satellite altimetry data. Variability in the Caribbean Sea is evident over several time scales. At the annual scale, sea surface height (SSH) varies mainly by a seasonal steric effect. Interannually, a longer cycle affects the SSH slope across the current and hence the intensity of the Caribbean Current. This cycle is found to be related to changes in the wind intensity, the wind stress curl, and El Niño–Southern Oscillation. At shorter time scales, eddies and meanders are observed in the Caribbean Current, and their propagation speed is explained by baroclinic instabilities under the combined effect of vertical shear and the β effect. Then the Loop Current (LC) is considered, focusing on the anticyclonic eddies shed by it and the intrusion of the LC into the Gulf of Mexico through time. Twelve of the 21 anticyclonic eddies observed to detach from the LC are shed from July to September, suggesting a seasonality in the timing of these events. Also, a relation is found between the intrusion of the LC into the Gulf of Mexico and the size of the eddies shed from it: larger intrusions trigger smaller eddies. A series of extreme LC intrusions into the Gulf of Mexico, when the LC is observed as far as 92°W, are described. The analyses herein suggest that the frequency of such events has increased in recent years, with only one event occurring in 1993 versus three from 2002 to 2006. Transport through the Straits of Florida appears to decrease during these extreme intrusions.