I used to sail an ODay 222 on the Bay out of Tabbs Creek in Virginia. You should be fine in your 23 footer, unless a strong front with gusty winds comes through. That's why you need to listen to what Paul is saying. Be aware of all the safe anchorages along your route
so you can duck in if things get dicey. If you get caught in a blow, you may only be able to run off before the wind
, so look for shelter on the Eastern Shore side.
Besides your charts
, be sure to buy a good, recent cruising guide to the Bay--it will give you all the info you need, including sketch charts
of entrances to the cozy little anchorages that you'll be able to access with your boat.
Watch out at the mouth of the Potomac
, as Paul suggests. Likely the roughest area of the Bay when conditions are bad.
Tangier is an interesting stop, if you have time. Be aware that the inflowing tidal currents are a bit stronger on the eastern side of the Bay. The creeks over there are twisty with many shoals, and the low marshes don't give a lot of lee shelter if it's blowing hard.
If you stay to the western side, some anchorages in Virginia are Mill Creek (off the Great Wicomico), Indian Creek (small marina with fuel
3 miles in, 1 mile walk to Kilmarnock for provisions/restaurants, or hitch a ride), Jackson Creek (south of Stingray Point), Horn Harbor (north of New Point Comfort-ssulivan got in there with his catamaran), Salt
Ponds (Hampton area), then Portsmouth/Norfolk.