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In the U.S...
North: The U.S. Canadian border crossing at Pembina, N.D/Manitoba. ( I had to look up whether this crossing point was further north than the one at the Vermont/Quebec border I used & it was.)
South: Naples, Fl.
East: Boston Harbor/Logan Airport
West: Offshore from Mana Point near the Barking Sands Missile Range on the west coast of Kauai, Hawaii
East: Looking at a map, Ogunquit is also furthest East I've been, but Boston is a close second. Outside the US, the furthest East I've been is Vietri Sul Mare (Salerno), Italy.
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