Coastal NJ vs Chesapeake
Howdy.. I have sailes both.
The Chesepeake certainly does offer more "diverse" sailing and detinations. I agree with you regarding the July and August heat and lack of any (challenging)worthwhile breeze (most of the time).
We have a house in Loveladies in Long Beach Island, right on the bay where we also keep two boats. We are planning on keeping our new catalina 350 either at High Bar Harbor Yacht Club in Barnegat Light, Or at the Trump Marina in Atlantic City. We are also in the same situation with two little kids. High Bar is a fantastic spot with a Life guarded heated pool, yacht club entertainment room, Outdoor grills, activiities and a short car ride to the beach and light house. The Inlet is right around the corner and there are quite a few boats that draw close to and over 5 feet. You can pretty much go in and out all day long if yo want to. I would not go down Oyster Creek Channel to the bay though. You will bump bottom a few times and the big Power Boats goining in and out of the inlet will push you toward the outside of the narrow channel. So if you want good ocean day sailing and perhaps weekend overnights to Atlantic City, Cape May Point Pleasent. This wold be a good spot for you. The slips are Privately owned and rent for about $4000 for the season. They sell out every year. (A slip can be purchased for right around $30,000 if there are any available. Even if you don''t stay there, you can enjoy the tax benefits of ownership and income revenue of renting to someone else.)High Bar Harbor is "rustic", offers a fully equipped yacht club and lots of beach things to do on LBI. There are some marinas on the southern side of the island like Beach Haven Yacht Club. You have to motor about 45 minutes to get out on the ocean though. 5 feet draft is no probem during your trek back and forth.
Almost directly accross on the Bay side there is Mariners Marina, an all sailing marina. The boats however have an average draw of just over 4 feet. I think you could get away with 5 feet but it is probably not worth the agravation. You might want to call them and ask. I strongly advise keeping your boat on the ocean side, not the mainland.
Atlantic City (Trump) is a Strate Marina and therefore the boat must be registered in NJ to stay there for the season. You can however take an extended "vacation" stay there. The very wide inlet is very well lit, is about 40 + feet deep, You can''t miss it even if you tried as the casinos provide a very "pretty" skyline at night. There is entertainment on the marina deck on Friday and Sat nights. Lot''s of kids show off there dancing skills. They also have a heated pool and fully equipped health and fitness club for your use. If you have a sitter, It is great to be able to take in a show or walk the boards at night after a ling days'' sail. Who would have thought that Atlantic City can actually be an enjoayable place to keep a boat. The fee there for the season is about $3750. For the year, (in water storage turbine slip) add another $1000. Or go over to Brigatine as there are some places on that side of the inlet as well that offer quick access to the inlet.
Hope I was able to provide you some insight to coastal NJ sailing in the area you are interested in.
Good luck with what ever you decide.