Hi N,
We have done extended cruising on smaller boats - your 31 has plenty of storage, it will just look different from what you're used to in your kitchen and closets at home. You will need cookware, plates, drinking glasses, and silverware - but, you don't have to go overboard (pun intended) with buying stuff: a pot and a pan and paper plates and plastic cups will suffice while you decide what will fit your storage area and what will work best on the boat. Assuming you aren't taking a family of 8 on this two week cruise, a service for 4 will do fine - unbreakable is handy. Buy some non-skid material to put between plates and line any shelves to keep things from moving.
You don't have to pack clothing for every day of the trip - most marinas have laundry facilities, and you will meet some interesting people who have good local knowledge they will gladly share with you. Plenty of civilization around the Cheseapeake, so you will be able get to stores to provision. Take clothes you can layer - if a shirt is a top layer, you can get another day out of it later. Get food that is easy to prepare, preferably one-pan type meals for this first outing. You will gain a lot of space in the fridge if you remove packaging from foods (since most are in plastic anyway).
Learn to be conservative with water usage and monitor your battery usage. Don't expect everything to go perfectly smooth on this shakedown cruise, so bringing a sense of humor will be very helpful.
If you have the opportunity to take a US Power Squadron or Coast Guard AUX Safe Boating Class before your trip, you will learn a lot from the class and other people in the class.
Have fun!
