I agree with most of these reccommendations
r.w. I agree with most of this. If you are putting in at Sand Point there are several "must see's". Annapolis, of course. Marinas & mooring buoys available. Anchoring is available but the boat will be pretty rocky. Plenty of Restaurants and interesting places (see St. Mary's church). There are some quiet anchorages up the Severn or up one of the creeks off of Whitehall Bay. South of Annapolis, Harness Creek off the Southern River or the Rhode River are both nice anchorages. Solomons is great but a bit of a sail. Plenty of marinas, restaurants and points of interest. Anchoring is also available. Not far from Solomons, Vera's on the St Leonard creek is an interesting place. It just recently changed hands and underwent some rennovation. I hope it still has all the character and charm it previously had and IMHO the St. Leonard creek is one of the top 5 prettiest creek on the bay. As trailer sailors you guys can take advantage of an offbeat little place called Chesapeake Beach. The marina there are not much (the people were great) but there are several resaturants right there. There is a free Chesapeake Beach/Railroad Museum housed in the old train station about 100 yds from the marina that tells the interesting history of this former resort/amusement park destination (it was really quite the place at the turn of the last century). The big draw is a water park within walking distance for the kids (and the young at heart). Ask the marina if they have any discount coupons. Deep draft vessels should avoid the entrance channel. An alternative is to stay at Herrington Harbour South and take a the marinas free shuttle to Chesapeake Beach. HHS is very nice with a beach, a pool and a restaurant. I'd been to Ches. Beach in my old boat (less draft) and really enjoyed the place. I took my sailing club to HHS and the shuttle to Ches. Beach this year and everybody loved it. Heading North from Sandy Point there are plenty of anchorages on the Magothy River. Eagle's Cove, behind Gibson Island was already mentioned. Further north is the Patapsco River to Baltimore's inner harbor. You could easily spend 3 days there, too many restaurants to name, the National Aquarium, the USS Constellation, museums and plenty of restaurants. Anchoring is limited. Bodkin Creek on the south side of the Patapsco was mentioned and has anchoring and marinas. I reccommend Pleasure Cove, they have a nice Crab House there and you can anchor right outside the marina. Across the bay go to Rock Hall. I'd avoid the front entrance and go around the back to Swan Creek. Great anchorage, several marinas and you can catch the Rock Hall Trolley to town. The Chester River has some nice creeks but time your sail with the tide . Trying to fight an outgoing tide heading into the Chester in a trailer sailor will make that 5-7 miles seem like 20 (my recomendation...avoid it, there's plenty elsewhere). Nice anchorages include Reed Creek (no services, tricky entrance) Langford Creek (at least 1 marina), Grey's Inn Creek (1 marina) and the Corsica River. Queenstown is quaint and centerboard boats should have no problem. Chestertown is nice but it's a long way up river and you'll probably be motoring. You will probably have to pass through Kent Narrows at some point in your week. Yes, there has been some shoaling in the entrance channel on the Chester River side but your centerboards should not have a problem. Kent Narrows may be a nice place for lunch but I don't think your "quiet" group will enjoy it for a overnighter. Lots of restaurants but a bit of a "party" reputation. St Michaels is a must see. The restaurants, Maritime Museum and history (St. Mike's foiled a nighttime attack by the British Navy by hanging lanterns in the trees up river and turning out the lights in town to fool them into shelling the wrong place, war of 1812)make this a great stop. Marinas are a little pricey, plenty of anchoring available. Another "Top 5" prettiest creeks is the Wye River. Plenty of $$$ here. It is mostly surrounded by the Wye Island Natural Resource area. Former President Clinton heald talks here with Menachin Bagen (sp?) of Isreal. When Bagen died, Clinton gathered a few stones from the Wye for his tombstone. The water runs deep shore to shore, try Dividing Creek, off the East Branch. Another nearby quiet anchorage (no services) is Tilghman Creek. There are plenty of great places on the Chesapeake. Too many to mention here. I'll never get to all of them in my lifetime. If you find a nice one, let me know. Tom Brown s/v Orion's Child
