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coords = First@Interpreter["StreetAddress"]["14 James Way, Cambridge MA"]; 

For the first part of the question, you can extract and post-process the callout graphics primitives from ListPlot[Callout[..]] and use them with GeoGraphics:

GeoGraphics[{Polygon[Entity["City", {"Cambridge", "Massachusetts", "UnitedStates"}]], 
  GeoMarker[coords, Style["\[FilledCircle]", 14, Blue]],
  Cases[ListPlot[{Callout[coords, "Hi", "CalloutStyle" -> Red]}], _GraphicsGroup, All] /. 
     Offset[a_, b_] :> Offset[a, GeoPosition[b]]}]

Alternatively, you can use the CalloutMarker as the GeoMarker:

GeoGraphics[{Polygon[Entity["City", {"Cambridge", "Massachusetts", "UnitedStates"}]], 
  Cases[ListPlot[{Callout[coords, "Hi", "CalloutStyle" -> Red, 
       CalloutMarker -> "Star"]}], _GraphicsGroup, All] /.
   {Offset[a_, b_] :> Offset[a, GeoPosition[b]], 
    Inset[a_, b_, c__] :> Inset[a, GeoGridPosition[GeoPosition[b], "Mercator"], c]}}]

coords = First@Interpreter["StreetAddress"]["14 James Way, Cambridge MA"]; 

For the first part of the question, you can extract and post-process the callout graphics primitives from ListPlot[Callout[..]] and use them with GeoGraphics:

GeoGraphics[{Polygon[Entity["City", {"Cambridge", "Massachusetts", "UnitedStates"}]], 
  GeoMarker[coords, Style["\[FilledCircle]", 14, Blue]],
  Cases[ListPlot[{Callout[coords, "Hi", "CalloutStyle" -> Red]}], _GraphicsGroup, All] /. 
     Offset[a_, b_] :> Offset[a, GeoPosition[b]]}]

Alternatively, you can use the CalloutMarker as the GeoMarker:

GeoGraphics[{Polygon[Entity["City", {"Cambridge", "Massachusetts", "UnitedStates"}]], 
  Cases[ListPlot[{Callout[coords, "Hi", "CalloutStyle" -> Red, 
       CalloutMarker -> "Star"]}], _GraphicsGroup, All] /.
   {Offset[a_, b_] :> Offset[a, GeoPosition[b]], 
    Inset[a_, b_, c__] :> Inset[a, GeoGridPosition[GeoPosition[b], "Mercator"], c]}}]

With the options GeoProjection -> {"Bonne", "Centering" -> {0, 0}} and GeoRange -> "World" we get

coords = First@Interpreter["StreetAddress"]["14 James Way, Cambridge MA"]; 

For the first part of the question, you can extract and post-process the callout graphics primitives from ListPlot[Callout[..]] and use them with GeoGraphics:

GeoGraphics[{Polygon[Entity["City", {"Cambridge", "Massachusetts", "UnitedStates"}]], 
  GeoMarker[coords, Style["\[FilledCircle]", 14, Blue]],
  Cases[ListPlot[{Callout[coords, "Hi", "CalloutStyle" -> Red]}], _GraphicsGroup, All] /. 
     Offset[a_, b_] :> Offset[a, GeoGridPosition[GeoPosition[b], "Mercator"]]}]

Alternatively, you can use the CalloutMarker as the GeoMarker:

GeoGraphics[{Polygon[Entity["City", {"Cambridge", "Massachusetts", "UnitedStates"}]], 
  Cases[ListPlot[{Callout[coords, "Hi", "CalloutStyle" -> Red, 
       CalloutMarker -> "Star"]}], _GraphicsGroup, All] /.
   {Offset[a_, b_] :> Offset[a, GeoGridPosition[GeoPosition[b], "Mercator"]], 
    Inset[a_, b_, c__] :> Inset[a, GeoGridPosition[GeoPosition[b], "Mercator"], c]}}]

coords = First@Interpreter["StreetAddress"]["14 James Way, Cambridge MA"]; 

For the first part of the question, you can extract and post-process the callout graphics primitives from ListPlot[Callout[..]] and use them with GeoGraphics:

GeoGraphics[{Polygon[Entity["City", {"Cambridge", "Massachusetts", "UnitedStates"}]], 
  GeoMarker[coords, Style["\[FilledCircle]", 14, Blue]],
  Cases[ListPlot[{Callout[coords, "Hi", "CalloutStyle" -> Red]}], _GraphicsGroup, All] /. 
     Offset[a_, b_] :> Offset[a, GeoPosition[b]]}]

Alternatively, you can use the CalloutMarker as the GeoMarker:

GeoGraphics[{Polygon[Entity["City", {"Cambridge", "Massachusetts", "UnitedStates"}]], 
  Cases[ListPlot[{Callout[coords, "Hi", "CalloutStyle" -> Red, 
       CalloutMarker -> "Star"]}], _GraphicsGroup, All] /.
   {Offset[a_, b_] :> Offset[a, GeoPosition[b]], 
    Inset[a_, b_, c__] :> Inset[a, GeoGridPosition[GeoPosition[b], "Mercator"], c]}}]

coords = First@Interpreter["StreetAddress"]["14 James Way, Cambridge MA"]; 

For the first part of the question, you can extract and post-process the callout graphics primitives from ListPlot[Callout[..]] and use them with GeoGraphics:

GeoGraphics[{Polygon[Entity["City", {"Cambridge", "Massachusetts", "UnitedStates"}]], 
  GeoMarker[coords, Style["\[FilledCircle]", 14, Blue]],
  Cases[ListPlot[{Callout[coords, "Hi", "CalloutStyle" -> Red]}], _GraphicsGroup, All] /. 
     Offset[a_, b_] :> Offset[a, GeoGridPosition[GeoPosition[b], "Mercator"]]}]

coords = First@Interpreter["StreetAddress"]["14 James Way, Cambridge MA"]; 

For the first part of the question, you can extract and post-process the callout graphics primitives from ListPlot[Callout[..]] and use them with GeoGraphics:

GeoGraphics[{Polygon[Entity["City", {"Cambridge", "Massachusetts", "UnitedStates"}]], 
  GeoMarker[coords, Style["\[FilledCircle]", 14, Blue]],
  Cases[ListPlot[{Callout[coords, "Hi", "CalloutStyle" -> Red]}], _GraphicsGroup, All] /. 
     Offset[a_, b_] :> Offset[a, GeoGridPosition[GeoPosition[b], "Mercator"]]}]

Alternatively, you can use the CalloutMarker as the GeoMarker:

GeoGraphics[{Polygon[Entity["City", {"Cambridge", "Massachusetts", "UnitedStates"}]], 
  Cases[ListPlot[{Callout[coords, "Hi", "CalloutStyle" -> Red, 
       CalloutMarker -> "Star"]}], _GraphicsGroup, All] /.
   {Offset[a_, b_] :> Offset[a, GeoGridPosition[GeoPosition[b], "Mercator"]], 
    Inset[a_, b_, c__] :> Inset[a, GeoGridPosition[GeoPosition[b], "Mercator"], c]}}]