I spent a week last summer boating from DC to the mouth of the Chesapeake and back. It is pretty remote in places. Not exactly the Chesapeake Bay but still a lot of fun. Here's a list of places to consider visiting on your way up the river:
- Colonial Beach, VA: I recommend staying at Bayside Marina if you want to stay close to town or Colonial Beach Yacht Center if you want to stay in a resort setting. Eat at Denison's Grocery. Great restaurant and not really a grocery.
- Cole’s Point Marina, 190 Plantation Drive, Hague, VA: Great place to spend the night on a Friday or Saturday.
- Historic St. Mary's City, MD: Historic city within walking distance of the river. Spend a few hours walking around the city.
- Piney Point Lighthouse, Museum, and Historic Park, Piney Point, MD: Nice museum. Spend a couple of hour here.
- Shark's Tooth Island: Stop by, walk the beach, and look for petrified sharks teeth.
- Mallows Bay: Dumping ground for historic wooden ships. If the tide is low, worth a dinghy ride over.
- Tim's Rivershore Restaurant: Stop in for lunch or dinner on your way by.