I have done a lot of sections of the "ditch." My simple advice is: it is what you make of it. I singlehand and to me the ditch is simply a long slow slog. With the exception of the section from Norfolk to Morehead City I avoid it if all possible. Matanzas Inlet, Bouge Sound, the list of places I hate is long (and documented on my blog.) Every other day refueling costs, expensive restaurants with mediocre food, expensive nights in a marina to simply tie up overnight - not my cup of tea. Yes, you can anchor and I usually do. The frustration of seeing from my compass that I am heading North when the destination is South is an experience I prefer not to repeat.
All that said, it is the company you keep. If you are with someone(s) who can enjoy exploring along the way there are interesting places to stop. Personally I love Savannah, a long slog from the sea buoy but not far from the ICW intersection.
A couple of notes for your consideration:
1) If you are planning a 5 week (35 day) transit and you intend to stop in marinas each night you can assume a budget of about $200 per day or $7,000 for the trip. That is $50 for fuel, $50 for dining, and $100 for the marina. There are delivery Captains on this site that can give you an idea of what it would cost for them to deliver your boat to Florida. My guess is a lot less than $7,000.
2) The Chesapeake Bay is a very fun place to cruise. But the trip up from Cape May through the C&D Canal and down the Bay adds a couple of hundred miles to the trip. Cape May and Annapolis MD are at about the same latitude. So you will be backtracking up to the C&D canal. It is much more efficient to go offshore direct to Hampton Roads, into the ICW, and out at Morehead City for the sea.
3) Since you are in New Jersey it might make sense to move the boat to the upper Chesapeake for a year or two before you retire and take long weekends in the Bay. It can be a long drive from Barnegat but just transiting the Bay would be sad. It really is beautiful for cruising.
4) You can cut weeks off the transit by going outside at Morehead and heading South. If you are adventurous and have 5 weeks get a qualified Captain - head for Bermuda, drop down to the Bahamas, and recross the Stream into Florida - that would be a 5 week trip to remember. Or just get the Captain to help you work your way down the Coast.
Just some thoughts to entice your planning.
One last and important thought. The first rule of cruising is: Have a destination or
a date, but never a destination and
a date. More people have hurt themselves and their boats because they had to get to a destination by a certain time and were motivated to make bad decisions.
Fair winds and following seas