Denise - mgiguere is correct that you're probably already qualified.... but what's really encouraging is that you're looking to hedge your bet and get some on board experience. That's good because whether you really need the experience or not, it means that you're thinking and planning and that's the whole game.
Keep in mind that even with someone else on board, you simply can not rely upon them for experience. Though they may seem to have great experience, it may be less than yours in practice - we all know people who talk a great game and then fold under pressure. For instance, you don't know what my experience is even though I have lots of posts, a great avatar, and say that I have a 38' boat. Could be a sham. From what I can tell, you're already at a 90% solution by questioning the trip. My suggestion is that if you must take someone else along, make it someone with whom you've ALEADY sailed (sorry, Sailnet-ers).
The trip is pretty easy. Consider it a series of long day sails. As others have indicated, it's pretty easy until you get to the Salem Nuclear power plant. After that, it opens up a bit and is mostly a less scenic version of sailing the Chesapeake, but with more current. Speaking of which, IMO the current is most aggressive near the power plant, then gets better as the bay opens up. There are several bail-out places along the way, marinas, rivers and such. As to the current, stay out of the deep water and you'll be mostly out of the current.
I first did the trip when I was 18 and sailed the family Catalina 30 with my brother-in-law from Ocean City NJ to Annapolis. At the time (1977), we had no
GPS, LORAN and an undersized 1 cylinder Yanmar. We also didn't have a chart for the 5 mile stretch between the power plant and the C&D canal (see my posts in the Boneheaded Moves thread for what happened!!). You can do this. Pick July or August for the most tame (but hot) weather.
Good luck and have fun.