Large cyclonic eddies on the northern edge of the Florida Current are the dominant mesoscale features within the southern Straits of Florida. The most prominent of these features is a quasi-stationary eddy that forms near the Dry Tortugas. Our observations, compiled from 3 years of advanced very high resolution radiometer measurements in the Straits of Florida and Gulf of Mexico, demonstrate a strong relationship between the generation of anticyclonic rings from the Gulf of Mexico Loop Current and the evolution of Tortugas eddies within the southern Straits of Florida. In six cases, Tortugas eddies evolve from cyclonic frontal eddies which form along the boundary of the Loop Current. The eddies remain stationary near the Dry Tortugas until they are impacted by an approaching Loop Current frontal eddy. The length of time an eddy spends near the Dry Tortugas is increased when the Loop Current sheds an anticyclonic ring. The involvement of a Loop Current frontal eddy in the ring-shedding process results in a delay in its, and hence the Tortugas eddy's, downstream propagation. Results suggest that the lifetime of a Tortugas eddy can be as long as 140 days when a ring-shedding event occurs, or as short as 50 days in the absence of any ring-shedding events. Upon entering the Straits of Florida, the Tortugas eddies are deformed by the narrowing topography and shrink to approximately 55% of their original size as they propagated downstream. The shrinking of these eddies is accompanied by an accelerated translation from 5 km/d in the western Straits of Florida to 16 km/d in the east.