Weather

The first challenge of the trip is crossing the gulf stream safely. The gulf stream moves north off the coast of Florida at about 4 knots. This can be like riding a conveyor belt toward Europe as typical boat speed is about 6 knots so the net speed over ground (SOG) would be about 10 knots. However, when wind opposes current, BAD things happen, namely, very steep seas result. The gulf stream is about 60 miles wide at this point so optimally takes about 10 hours to cross.
Obtaining an appropriate weather window is critical to avoid a very rough start to the trip.

From Bermuda, the typical route to the Azores is to head a few hundred miles to the north of the islands and when roughly northwest of islands to head towards them. This is due to a high pressure system that frequents this area referred to as the Azores high.

Here's a cool map showing wind direction:
Add detail of how to obtain grib files via SSB, etc