It depends on how overwater you want to get.
A great circle route would take you through New York Oceanic, so HF radios are required. Also, depending on US rules, slide/rafts may also be required. (With Canadian rules, you can go up to 400nms without requiring rafts, so they would not be required).
By going south, then about 200nms north of NAS, heading along the islands would add about 200 nms to the flight, but HF radios would not be required.
Life jackets are required on either route.
Just because I stopped arguing, doesn't mean I think you are right. It just means I gave up!