One thing you did not mention is the Gulf Stream - the generally northern flowing warm water current coming out of the Gulf of Mexico. Most sailors try to minimize their time fighting against the Gulf Stream by going farther out in the ocean, to Bermuda almost to get past the current and then head south for the Caribbean Isles. The other choice is to go further south and head off across the Gulf Stream for the Bahamas and then southeast towards PR
and the VIs (the so-called Thorny Path).
Another problem with your scenario is that with 2 sailors and one prisoner trying to mostly sail towards S. America is that with only 2 reliable crew they should take turns standing watch/steering the boat. While one is on watch the other would usually rest for about 4 hours at a stretch. Someone also has to keep an eye on the 'prisoner' unless he/she is handcuffed or otherwise restrained (tied up - sailors like rope and knots) leaving little time for either crewmen to rest. The 'prisoner' would also have to make ablutions as this trip, if done totally offshore with good winds could take 2 - 3 weeks starting from NJ. They would need food, water and what not for that time as well.
It is a bit difficult to describe what standing a 4 hour watch would be on your vessel (not the 19' you linked to BTW) without knowing what equipment it carried. I think we are talking about a 30+ foot sailboat for 3 people.
On one blue water trip I helped with there was Radar, an autopilot hooked into a chart plotter, SAT phone, multiple GPS as well as VHF radio on a 50' Beneteau. The owner could have sailed it by himself but I was along to spell him on watches every 3 hours so he could rest up for his next shift at the helm. The off-watch crew would also be the one to prepare meals and clean up as obviously the helmsman would be concerned with the sails, the 'vector made good' or course and watching out for shipping and the weather. Many boats also carry a computer and either using SSB radio or a SAT phone they can download weather forecasts on the open ocean (look up 'grib files') as a forecast is only good for a few days, if that.
There is also a slight chance of a late hurricane or TS in the Atlantic in November although the hurricane season is largely over by then. Weather like that would certainly make life miserable for your fictional crew and captive.
The weather is it's own character as are the boat and the ocean.
You really owe it to yourself to at least hitch a ride on a sailboat in the 30 - ? foot range to see what it is like during the day time. At night it is a little more intense as you lose the visual horizon while the boat continues to move to the ocean swells (a calm ocean has 3' - 6' swells). Seeing the Milky Way and the stars at night is phenomenal if it is not coudy, as is the phosphorescence trails the boat leaves behind in warmer waters.
There is really too much to include in this reply.
I'd suggest reading a few blogs by folks who are doing some ocean traveling by sailboat. Here is one that comes to mind: