The CBBT is fishable in your bass boat on the perfect day. You must choose wisely as it can get very dangerous very fast in a small boat. On a nice calm late fall or early winter day you will see kayaks, jon boats and all sorts of other small craft along with sportfishers, cruisers, center consoles, etc. The other piece of your puzzle is to not leave from the Peninsula. The only place I would recommend launching from in a bass boat is the Crab Creek ramp at Lynnhaven Inlet. The ramp is off of Shore Drive between Norfolk and Virginia Beach. The inlet will put you at the base of the CBBT and about 3 miles from the 1st/2nd island complex. Safety equipment is also of huge importance when your fishing big water during a cold time of year on a boat with zero free board. Check on the coastal regulations, you will definitely need flares which are not required at Anna or on the Chick. The fishing can be phenomenal on light tackle around the islands and the pilings of the CBBT but extreme caution is recommended.
Go to message boards like Tidal Fish and meet some people and you can more than likely hop on others boats that are more equipped and less weather dependent.