Bermuda weather can surprise people by unexpected TRW, it's just on the outside of the Gulf Stream. When I flew cCitation II out there we checked the weather and the radar entering the BDA airspace. The plan was to turn around without leaving FL, if any TRW.
One airliner was surprised, held until fuel got tight, headed for BOS only to call it too close and land at Otis AFB.
GF