There have never been as many 'Pirates' at sea as it is now!
Start with the basic paper set up and a hand held GPS (remember to get one with NMEA out and cable for lap top). I have a couple of Garmin 86 without charts that have brought me 1/2 around the world.
When You start cruising around You will allways find someone with 'free' programs and charts. Do your own testing and decide what suits Your own needs and requirements. Personally I preferr programs where tides are integrated as it makes it more easy and simpler to determine currents and tides at your position.