Good advice
There are tons of scenic and nice places in the Chesapeake. I wish on my two trips through there that I would have had more time to stop and smell the roses. But if your mind is made up to go to the islands, then by all means go for it. But, DO NOT run the ICW at night. I can assure you that you will be aground many many times if you do. Shoals build up at the inlets so fast, they have a hard time keeping the bouys in the proper places. Most of them are nuns and cans, unlighted. It is difficult at times, to make 50 mile days. Bridges open on schedules, so waits for them are common. In Georgia, North and South Carolina the tides are 8' or more a day. Anchoring and navigating shallower areas takes some planning. Doing the ICW is a good experience too, but needs to be done when time is available, and a tight schedule is not necessary. Jump offshore, and do some overnighters. The experiecne will be a good way to learn the boat, it's systems, and yourselves. There are a lot of inlets to get into, should things go bad. Get yourself a Skipper Bobs waterway guide. There is a ton of good info. in it, and will tell you which inlets to shy away from, and which ones are safe, and have good anchorages. Good luck, good weather, and enjoy.