You can add the polygon of the US in the GeoListPlot result with something like this:

GeoListPlot[{WeatherData[{38.4916, -122.1241}], 
  WeatherData[{25.8175, -80.2858}], 
  Polygon[Entity["Country", "UnitedStates"]]}, 
 GeoBackground -> GeoStyling["ReliefMap"]]

(Note that now there is no need of the GeoRange specification, because we get the map bounds from its geo primitives.)

Or you can use GeoGraphics directly with something like

GeoGraphics[{Thick, GeoBoundary[Entity["Country", "UnitedStates"]], 
  GeoMarker@WeatherData[{38.4916, -122.1241}], 
  GeoMarker@WeatherData[{25.8175, -80.2858}]}, 
 GeoBackground -> GeoStyling["ReliefMap"]]

I see. I used features of WL 12.2. You are probably using a previous version. Then try this:

GeoGraphics[{{EdgeForm[Directive[Black, Thick]], FaceForm[], 
   Polygon[Entity["Country", "UnitedStates"]]}, 
  GeoMarker@WeatherData[{38.4916, -122.1241}], 
  GeoMarker@WeatherData[{25.8175, -80.2858}]}, 
 GeoBackground -> GeoStyling["ReliefMap"]]

Is this what you want?

GeoListPlot[{WeatherData[{38.4916, -122.1241}], WeatherData[{25.8175, -80.2858}]}, 
 GeoBackground -> GeoStyling["ReliefMap"], 
 GeoRange -> Entity["Country", "UnitedStates"]]