Chef,
Great Idea. There are
lots of great stops to the south. We just moved back after 6-years sailing south from Solomons. Here are some of our favorites:
Onancock: A
must, we think this is the prettiest port on the Bay. A tall statement on a Bay loaded with pretty places. (click on my avatar above for a pic of the Wharf) You wind ~5-nm up the creek to get there but it is deep enough and worth the motor. Anchor in the small pond just off the wharf. There is room for 4-5 boats on reasonable scope. Or, call the "Onancock Wharf" and get a slip - they offer 4-5 at any one time. Get there on a Sunday or weekday to assure a slip if that is what you want. Dine at the Mallard, or the Charlotte Hotel up town. I will be interested in you opinion if you do. Tour the mansion up town if your little ones can take it. From the wharf you can take a ferry to Tangier Island as a day trip if you like.
Mill Ck (one of many) this one just south of the Great Wiciomico Light offers a great anchorage and the ability to go for a swim if desired. No facilities, but a great place to anchor - often in seclusion against a deep (for the Chesapeake) (8') bank.
Urbanna, VA: Another in "The Prettiest" category. This one is up the Rappohannock but worth the time. You can sail the river, it carries good depth bank to bank. It must also carry a bit of current though - Virginia Dare points very well, even so the chart-plotter track looked like an accordion when I last sailed it. The channel is easy entry for your draft. Take a tie at one of the marinas here because you will want to make lots of trips up-town. Good restaurants in town though not in the class of the two I recommended in Onancock. A pizza place if the kids are ready for that and some interesting historical houses. You will want to spend 2-nights here. It too has a nice little pond once inside that can hold a dozen or more boats at anchor if that is your preference. We always use the Urbanna Town Marina, but you can't go wrong. They offer a free dinghy dock (well inside) if you anchor.
Yorktown: By all means take a tie at Riverwalk Landing on the York. Some cruising guides have not updated for Riverwalk yet. People still think they have to go across to the north side to get a slip - no need. If you tie at Riverwalk you walk less than a block to a free trolly that will get you transportation to all the history of the area, Williamsburg, Yorktown Battlefield, Jamestown Colony. The marina is a floating pier in 60-feet of water just downstream of the bridge. It is set up so well that you could drive a barge in for a tie. No weaving through a maze of dock & piers. Restaurants are Good - again, not great.
Cape Charles: this is like a Gin Martini, you like it or don't. We love it (both actually). It is still a real place that still has a soul of its own - no phony baloney fudge and ice cream shops with a parade of tourists here. We have never tried the long channel to Kings Ck. we drag too much lead - or too low anyway. We go into the Town Marina. It is actually a pretty good marina, but situated in a very industrial setting. You will be tied right behind the USCG Cape Charles station that will gently wake you with reveilee in the a.m. Not to worry - take the hike across the railroad tracks to town. It is a very interesting little town that is showing the signs of a comeback from an economic coup de gras when the Bridge/Tunnel complex left it "high and dry" in the 60s. There is a very good restaurant and an excellent Pub there that I point out in the Chesapeake Good Eats .pdf. Try both.
Chesapeake Good Eats. pdf
Norfolk: If you make it this far south - you probably haven't done justice to the recommendations above - or you have lots of vacation time ;-) In any case tie at The Waterside Marina. They charge a $1.50 a foot and treat you like it was $4.00 a foot. There is a Brazilian restaurant up town (in the .pdf) that both adults and the kids may be interested in - don't forget to bring the MasterCard though. If you like
Diners, Drive-ins and Dives, with Guy Fieri, on the Food Network take the
free bus (long walk) to Doumar's on 1919 Monticello Ave. The inventor of the ice cream cone and a great "quirky" place for lunch or dinner. Lots to do in Norfolk and the area in this part is new, clean, safe and very attractive.