That's a pretty good start, Dave.
"Worton Creek, Rock Hall, Chestertown (generally a long motor up the river), Middle River (some great burgers, not the best scenery), Back Creek in Annapolis, Galesville, Cambridge, Easton, Oxford, St Micheals, Crisfield, Urbanna, Hampton.
If you are heading up the Potomac add Cobb Island, Colonial Beach, Mattawoman Creek, Occoquan (long dinghy ride if you won't clear the bridges), Washington Sailing Marina, Alexandria, Washington Channel."
Depending upon the wind, the trip up the Havre de Grace channel usually involves about 6 miles of motoring to reach Havre de Grace. The channel is fairly wide, about 200 yards in most places, and with the exception of a single turn at Battery Island, it's straight as a poker.
Lots of restaurants in Havre de Grace, some waterside, and others within a short walk. Some touristy stuff to see, Decoy Museum, Concord Light, etc... You could spend the entire day there and not see everything in this relatively small town.
From Havre de Grace to Port Deposit is about 5 miles upriver and though I have sailed this a few times, much will depend on wind direction. The channel is only about 100 yards wide on the east side of the river and the fixed bridge clearance is just 50 feet for the railroad bridge and US 40. Depths never get below 10 feet in the channel. The preferred route is to pass beneath the railroad bridge at Havre de Grace, then immediately turn east and parallel the bridge staying about 50 feet above the bridge and cross the lower end of the Garret Island Bar, where depths come up to about 8 feet. Shortly after crossing the bar, the bottom will fall off to 55 feet and in some places 70 feet. Turn left and head upriver, and follow the markers. There are no markers above the I-95 Bridge, but if you watch your depth finder and stay within 100 feet of the eastern shore of the river, you will have no problem reaching Port Deposit.
At the southern end of the Havre de Grace Channel, there are two spoils islands, locations where you'll find great anchorage and excellent beaches that have been created. During the week, these islands get some visitors, and weekends are jammed with throngs of boaters and swimmers.
The Sassafras River is quite long and the channel winds around a lot, but it's a neat river to explore. If the wind is blowing from the west, you can sail upriver all the way to the Route 213 Bridge, where you'll find the Kitty Knight House, located just up the hill from the Georgetown Yacht Basin.
Restaurant | kittyknight.com
If the wind is blowing from the south, you'll find a great anchorage in the back end of Still Pond Cove, where you'll often find no more than a dozen or so other sailors, all watching the sun go down and toasting to another fun day on the bay. I've spend many comfortable nights there. However, it's not a good place to be if the wind is woofing from the west or northwest. Under those circumstances, go around the corner to Worton Creek. The creek is relatively shallow, and the channel is a bit narrow, but quite manageable. At the top end of the creek, there is a good anchorage that is hurricane proof. At the top of the hill, there is a nice restaurant, Harbor House Restaurant.
Fairlee Creek is just a bit farther south, jammed with throngs of party goers rafted up on weekends, but weekdays are fairly calm. The channel leading into the creek has recently shoaled and I don't know if anything has been done during the winter to alleviate the situation. Also, the currents can be very tricky at the mouth of the creek, so entrance is best done at slack, high tide. Once inside you'll find Great Oaks Landing Marina, Jellyfish Joel's Tiki Bar, and Mangrove's. The prices are somewhat high, but the food is usually pretty good. Stay away from here on the weekends - It's a zoo.
Rock Hall can be a bit tricky entering the basin, but the channel is well marked, a bit windy, but once inside, you find some great sites to see and some touristy restaurants. Among the most popular is the Watermen's Crab House and Bar, which serves a great softshell crab sandwich during the summer months.
Straight across the bay you'll find Gibson Island, which long before I was born was owned by my father's great aunt. When my father was just a kid, he would drive his great aunt's model A Ford across the Gibson Island bar, transporting weekend guests to her mansion on the island. Her mansion was all brick and can be seen as you enter the mouth of the river sitting high upon the hill with an incredible view of the bay. There is a long, beach house a few hundred feet from the tip of the island, which was also constructed and owned by my dad's great aunt. She sold the island sometime during the 1920s and purchased a large farm just north of Towson, MD.
Shortly after entering the Magothy River, you can turn left and enter Deep Creek, where you'll find the Deep Creek Marina and Restaurant. I have not been there in years, so you will have to go by the reviews as to the food and service.
Deep Creek Restaurant
Along the river's north shore is where you'll find Dobbin's Island, which is a very popular anchorage that is fairly well protected. I've spent several nights there in quiet comfort, but weekend party goers tend to take the location over during mid summer.
it's only a short sail from the Magothy to Annapolis, and all the town has to offer has been talked about on this and other forums so I don't need to go into details here.
A short day's sail down the bay past Bloody Point at the tip of Kent Island will put you into Eastern Bay, the Miles River and Saint Michaels, which is a bit of a tourist trap, but can be fun just to walk through the town and browse the shops. Some of the restaurants are pretty good, and many years ago, I played music in some of them, but that's another story.
A bit farther down the bay and you can easily enter the Choptank River and head upriver to the town of Oxford, which is definitely a sailing town. Good waterside restaurants, reasonable prices at most, but some are ridiculously overpriced and overrated. Plenty of places to anchor for the night, and some are fairly well protected.
Depending upon your draft, you can shorten the trip to Oxford by heading through Knapps Narrows, which is best negotiated during slack tide. The bridge opens upon demand, but when the tide is screaming through the bridge pilings, it can be a bit hairy. There are some nice restaurants in the narrows that are worth a stop.
http://tilghmandining.com/
Across the bay from Tilghman Point is Chesapeake Beach and the Rod & Reel Resort and Spa. The entrance channel is narrow and a bit shallow at times, but constant maintenance by the owners keeps it navigable most of the time. The restaurant is superb, and there is a lot to see and do here.
Rod N Reel Restaurant | Chesapeake Beach Hotel & Spa There is a nearby water park that is a fun place for the kids, and on the premises of the resort is a railroad museum that I love to visit.
It's a full day's sail from Chesapeake Beach to Solomons, and you'll pass some historic and interesting features along the way. If the weather is relatively calm, I used to anchor off Calvert Cliffs and snorkel in the shallows where I found loads of prehistoric sharks teeth, some measuring up to 5 inches across. You'll pass the LNG Gas Docks, Cove Point Light, Then make a right turn and enter the Patuxent River. There's a deep channel that goes up the north shore and allows you easy entrance to Back Creek. Lots of things to see and do at Solomons - just Google it and you will have a good list to select from.
It's a short day's sail south to the mouth of the Potomac River which provides some of the bay's best sailing opportunities. Point Lookout Bar projects a quarter mile out into the river, so be careful to stay in the channel until passing the bar. Point Lookout State Park has a great Civil War Museum that is worth a stop there, and you anchor up inside Lake Canoy. The anchorage is quite small and not very deep so use caution here.
Upriver, at the mouth of Smith Creek is Courtney's Restaurant and Marina. The food is typical southern Maryland, mostly fried, but pretty tasty. Inside the creek is where Scheible's Fishing Center and Restaurant is located, but it has long since closed down. Rumor has it, though, that it will be reopening this spring - not sure yet.
Saint Mary's City is a nice trip upriver and worth a visit. Lots of neat things to see there, too.
If you have a shallow draft boat, you can go across Chesapeake Bay to Smith Island. At high tide, you should be able to enter the bayside inlet and get to Allen Tyler's Chesapeake Inn. A tour of the island can be fun and educational.
http://www.nytimes.com/2008/09/26/greathomesanddestinations/26havens.html
It's an easy sail around the top end of Smith Island and into Tangier Sound where you'll find Crisfield. Crisfield, at one time in history, was a thriving town, but it's survival depended heavily upon the seafood industry, which no longer has the ability to support an entire city. Consequently, the town is in a state of change, but there are a few good restaurants there and a nice marina.
A half-days sail to the south and you will find Tangier Island, which in many ways mimics Smith Island. It's a neat place to visit for a half day, then you can anchor up for the night in the habor.
it's a day's sail to the mouth of the Rappahannock River, and up to Locklie's Marina, which is where you will find a great seafood restaurant.
https://www.rroysters.com/restaurants/merroir There are lots of places to anchor, most of them sheltered to some degree.
From the Rappahannock River, it's a long day's sail to Cape Charles, which is one of my favorite places to visit on the lower reaches of Chesapeake Bay. It one point, the town was essentially dying, a whistle stop for the Eastern Shore Railroad where the trains were loaded on barges and transported across the bay to Norfolk. The town has since transformed, it has a resort, golf course, and many new, exquisite homes along the bay's shores. There are also many historic homes, stately mansions, overlooking the water of the bay here. When I first went to Kings Creek Marina, which was 50 years ago, it was a falling down pier, with a few shacks that watermen lived in. Today, it's a huge marina/resort complex with all the trimmings.
The Oyster Farm At Kings Creek (Cape Charles, VA) - Lodge Reviews - TripAdvisor
Just a short sail to the south is where you'll find Kiptopeke State Park, which is a wonderful place for the kids to swim and wander the beach trails through the dunes. It's also where you'll see a dozen concrete liberty ships sitting upon the bottom of the bay, end to end, creating a seawall that was used to protect the old Kiptopeke Fair Landing, which was the only way to cross the bay prior to the construction of the Chesapeake Bay Bridge Tunnel. It's also a great anchorage that is protected from most westerly and southwesterly winds.
Kiptopeke State Park
This is just a primer of the locations I've visited on Chesapeake Bay during my 60+ years on the water. There are many more exciting locations to explore and visit, more than most folks will see in their lifetimes.
Hope this is helpful,
Gary