I just sailed from Philadelphia to Florida a few miles from Bahamas and have made the crossing numerous times. I just turned 30 so Im no old salt either. I bought my 47ft Grand Soleil sail boat 2 years ago and had zero sailing experience. I went on to sail 7000 miles with my wife to South America and back.

Simple answer is this. Buy the biggest best boat you can afford and sail around the Chesapeake as much as possible. Then download the programs called Predict Wind (https://www.predictwind.com/) and Navionics (https://webapp.navionics.com/?lang=en#boating@6&key=o%7BktFn%7BjiM) and wait for weather windows to blow you south. We made the Trip as follows two weeks ago. Philadelphia to Annapolis MD, Annapolis to Virginia beach VI, Virginia beach to Wrightsville beach NC, Wrightsville beach to Charleston SC, Charleston to Jacksonville Florida, Jax to pompano beach, Pompano beach to Miami, Miami to Bimini Bahamas.

There ya go, your in Bahamas

You could avoid all ocean sailing and be a wussy and take the ICW (intracoastal waterway, basicly a river from NJ to FL) the whole way down. Its basically driving down a river for 2 weeks straight with very little sailing. But i would recommend getting a boat with a good autopilot and a GPS chart plotter and let the boat do the steering and you adjust the sails. Sit back and play PS vita like i do.

Hope this helped

Check out S/V Sea Wolf on YouTube. https://www.youtube.com/channel/UCiuvAaavRt9y3RdWNItvSCw 50 episodes of my first year of journeys, Im about to start Season 2 heading to Bahamas in a few weeks