Re: 2012 Summer Trip from NY to NJ
OK.. where to start... Your IPad.. You need at minimum Chart plotter/ GPS/ with depth. Don't plan on running at night or in poor visibility. Even in the ICW you need solid electronics and sold charting skills. The IPad is good for checking weather and e mail. Make sure you have the 3-g activated on it so you can get up to the minute weather radar when out on the water.
The grill is an easy yes, get one. If your wanting to heat anything from a steak to a couple of eggs in a fry pan, (I'll take mine over easy) is a great thing to have on any boat. I have a ketal grill that mounts in a rod holder. One small propane bottle will give you about 10 meals. Relying on restaurants, finding a mooring, the courtesy dock is filled, our launch is down, and a taxi driver just to get a burger and a cold beer doesn't seem like time well spent.
Your mold issue needs to be addressed.You need to get it cleaned. Bleach and water is the only way I found to really kill it. If it is more then mild surface mold in spotty areas, (Sounds like it is), I would strongly recommend tearing out whatever has mold on it and replacing it with a product that is mold resistant and easy to clean.
Mattresses can be custom made. If your boat has a dedicated berth, a nice inner spring mattress can give you a good night sleep and not wake up sore. Instead of spending money on a hotel, hook up your boat and upgrade you accommodations on board. Hot water heater, generator (Honda 2000), 12 volt fans,and on and on.
I think your time frame may be tight. I have a Monterey 250CR and have done a lot of long distance cruising with it. (Cape Cod to Nova Sotia as example) Mother nature can really mess up your time line as to where you want to go and when you will get there. Murphy was a boater and anything that can go wrong usually will. Pressing in poor conditions or with slight mechanical issues can be disastrous. When I am on long trips I find after 4-6 hours I am ready to stop and set up. I find I run the boat from very first light (5am) till around 1-2pm. By then you usually need fuel, ready for lunch, and the sea conditions, boat wakes, and winds have picked up. Can it be done in your tie frame? Yes, but you should plan on it taking twice as long as originally thought.
As for planning out your trip start with Google earth. Calculate fuel and the distance you can travel on 2/3 tank. Most marinas on Google earth you can click on and get there name and maybe website. Find pump out stations, grocery stores, and service areas that can fix your type of motor and outdrive.
Since you will have a plan as to what time you will be on the water, now you need to look at tides. If you are going to be going through an area where there is a concern because of draft, plan on hitting it a couple hours either side of high tide. I do know that very little money is being spent on the ICW but from friends of mine that go from Cape Cod to the Keys every fall and spring, I have not heard of it being impassable. Your new up to date charts and chart plotter should keep you out of trouble.
Full camper canvas is a must. Have a spare of everything. Have a dinghy with outboard.
To find more information on places to drop the hook and hang out for the night, find a forum for people that do the great loop. Lots of information there and they will add a lot more to your list then I did. Good luck and keep us posted on your planning and prep for your great adventure.