When you get to Portsmouth/Hampton buy the Chesapeake Bay Magazine Guide to Cruising the Chesapeake Bay. That will provide you with a study guide, navigation tips and information regarding the many great anchorages and towns. Tangier I can be tricky with lots of current and tight maneuvering - mind the tidal state. Maybe 3 or transient slips. Tangier sound is very remote and natural. Anchor outside if you have the skills. Norfolk waterfront is very walkable, Hampton is quaint. Reedville on the Great Wicomico River is worth a visit. Great oysters at Topping on the Rappahannock. St.Mary River (Potomac) is where Maryland colony began is home to the best sailing college on earth - St. Marys. Solomons Island at the Patuxent is a busy sailing town, has a nice museum, very walkable and lots of restaurants. Lots of boat services there and plenty of transience slips. Spring Cove Marina is lovely. The Little Choptank has the most natural protected anchorages (no services). Choptank River has historic Cambridge and Oxford, both are worth a visit and provide lots of entertainment. Herring Bay has a huge boatyard at Herrington Harbour North (Deale), lot of tradesmen. Herrington Harbour South is the nicest marina on the Chesapeake, great new restaurant and transient slips. Slips are expensive, but if you have a dink, anchor out in Herring bay. Galesville on the West River is nice with several working boatyards. Eastern Bay to St. Michaels takes you to the premier bay maritime museum. Wye River is loaded with plantation homes and some great anchorages. Annapolis is a must see and surprisingly affordable with the City mooring balls, very walkable, the USNA, very colonial with tons of shopping. Magothy River is a lovely anchorage. Kent Island is where powerboaters go to drink. Baltimore Inner Harbor marinas give you access to the Baltimore waterfront, restaurants, breweries, shops and Lil’ Italy.