The Gulf Stream is a massive current that passes up the East Coast of the United States. This meandering highway in the ocean has two definite areas that it will always pass by, the Straights of Florida and the Cape Hatteras. Everywhere else, the stream moves around on a daily basis.
There are horrible stories about hellish Gulf Stream crossings where the winds and seas build quickly, making the crossing a horrible endevour. Other times, people state that they crossed the Gulf Stream without even noticing its presence.
The trick to the Gulf Stream is to only cross it if the winds are flowing with the current. The current tends to run at around 3 knots from the South. If the winds are from the North, the winds and current will clash and form very steep and hellish seas. If the winds are from the South, along with the current, then the passage will be most mundane.
As you approach the Gulf Stream, the west wall will be your greatest challenge. If you are able to get over this hump in the ocean with favorable winds, you will simply be carried along by the current as you make your way to the other side. This will make for a very uneventful journey and a calm crossing. If the winds are blowing from the North, it would behoove you to heave to and wait for the winds to change, as jumping into the Gulf Stream at this time would be a huge mistake.