The Power Squadron in your area may offer a course in weather. A good book to have around is Chapman Piloting & Seamanship which has an excellent chapter on weather. It is available in either hard cover or electronic form.
For weather forecast I go to baydreaming.com which will provide both summary weather for the coming few days and daily forecast for each area of the bay. To determine if the forecast is holding up I use the WindAlert app which will provide you with current condition on and around the bay.
In the summer when storms are about I use MyRadar app to determine if storms are developing, there location and direction of travel. Thunderstorms on the bay can be extremely dangerous, especially those associated with a front. Popup storms are not generally as severe but can make you wonder why you took the boat out. Lighting associated with the storms can completely disable your engine by destroying the electronics. A few friends of mine have had this happen while they were out fishing. Also storms may be traveling 30 to 40 mph so it is hard to out run them, keep an eye out. During days when afternoon & evening thunderstorm are predicted I normally try to get to my destination by 3PM which normally avoids any problem.
Thanks. This is extremely helpful!
As a general rule of thumb winds of 5 to 10 knots will not give you any problem on the bay. When the wind is blowing 10 to 15 knots depending on where you are on the bay and the direction of the wind you may not be comfortable. If the wind is blowing out of the west, cruise close to the western shore; if the wind is blowing out of the east, cruise close to the eastern shore; and if the wind is blowing out of the north or south you'll have to take what you get.
As you gain experience on the Chesapeake you will find a 23' boat will provide you with years of exploring the bay.