Need suggestions for Chesapeake cruising destinations

SFS

.
Aug 18, 2015
2,066
Currently Boatless Okinawa
So we will make it to Norfolk tomorrow, and the Chesapeake will be our cruising grounds for the next 4 weeks. I've done a search here, and on CF, but would like firsthand suggestions on places not to be missed. The first two are apparently Tangier Island and Smith Island. What others should I take in?
 
Nov 26, 2008
1,966
Endeavour 42 Cruisin
2 to 3 days up the Potomac and you can anchor in the Washington Channel in DC. $5 dinghy dock fee at Gangplank and you can walk to the Mall, etc All the Smithsonian museums are free.
 
Sep 23, 2009
1,475
O'Day 34-At Last Rock Hall, Md
Of course, Annapolis. Moring balls are about 30 bucks and free dinghy docks. The free tour of the Naval Academy is worthwhile. Take photo id. Accross from the Academy class rooms is the Severn Inn with dock and dine and the best crab cakes. Outside tables and inside ac.
For a quieter time sail up the Severn to Round Bay.
 
Jan 22, 2008
8,050
Beneteau 323 Annapolis MD
...the Severn Inn with dock and dine and the best crab cakes. Outside tables and inside ac..
The last time I was at Severn Inn this year, they still had not rebuilt their docks from Isabell many years ago. There is/was enough space for ONE boat, though, on the main dock. /// You can dock at Canter's restaurant for crabs on the waterfron of (Mill?) creek- off the Severn, by the radio towers. Any ideas where you will park the boat?
 

Gunni

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Mar 16, 2010
5,937
Beneteau 411 Oceanis Annapolis
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.
 
Apr 21, 2014
184
Hunter 356 Middle River, MD
I would try as many different locations as you can to get a feel for the Chesapeake and it's endless rivers, coves and anchorages.
Have been all the way to DC up the Potomac but it is a long slog. Liked the Solomon Islands, quaint town and Maritime Museum. For a real small town feel check out Oxford on the Tred Avon River, then come out of the Choptank River and head north to St. Michaels on the Miles River, home to the Chesapeake Bay Maritime Museum. Also the Wye River is just north of that off of the Eastern Bay, great deep water anchorages and magnificent wildlife. Cross over to Annapolis to the west side and either anchor or take a mooring ball, good dinghy docks and walking friendly town with the Naval Academy, fantastic tour. North of the Bay Bridge is the Magothy River, and we absolutely love the anchorage right behind Gibson Island, with it's large, deep, and quiet cove with a picturest view of an old Maryland house/horse farm. To get a big city vibe go to Baltimore and sail past Fort McHenry and see the city erupt from sea.
I think the Chesapeake is a great place to sail, enjoy.
Jeff