no problem
A 30' boat in good order shouldn't have any trouble, assuming good decisions are made regarding weather and navigation. I would have done that trip in my 26' sailboat and not worried. My experience in the area is from crewing on a delivery that took 52 hrs running from Annapolis to Milfrod CT. We went up the chesapeake, through the C & D canal, down the delaware and out the cape may canal. We then went north into NY harbor, up the east river into long island sound and across to CT. By far, the worst part of the trip was the delaware. Steep, close together 4 -6 waves were a little rough. We had a 20 - 25 kt wind on our stern (it was fall, we had NW wind) so at least we were flying along. The conditions were caused by opposing wind & tide. We did have a Yachting magazine editor on board, which was nice. He is very familiar with the area and says the delaware is consistently one of his least favorite places to be on boat. Conditions are frequently less than ideal, and the scenery stinks! For this reason, if I were going to do this trip in the summer, I would go counter clockwise since the winds tend to be southerly in the summer. If you time the entrance to the delaware with an incoming tide, and have southerly winds, the water shouldn't be real rough and you can get through this section as fast as possible. If you go clockwise, and want to run with an outgoing tide, chances are the winds will oppose the tide and if the winds are strong you have uncomfortable, but definitely managable conditions. Also keep in mind there will be a considerable amount of shipping traffic on the delaware. To sum it up, chances are the worst you are looking at on a 30' boat is discomfort for some of the trip. This sounds like something I would like to try the next time I have the chance, and when I do, I am going to focus on making the delaware as easy going as possible and pay close attention to the weather when I run outside. Everywhere else is just a matter of dealing with navigating inshore waters and dealing with weather just the same as on any inland bay or waterway. Good luck and have fun!