Best Random Cruises Ever

The author sets out to prove that even a blindfolded editor with sticky tape can choose a dozen dynamite Bay destinations.

by Jody Argo Schroath

“Yada, yadda, yadda . . .” I say, bragging to my friend and cruising buddy Jean about the Chesapeake Bay. We are anchored in San Carlos Bay, a hundred yards off the southern end of Florida’s Sanibel Island, and I am extolling the virtues of cruising on the Bay. As usual.

“The Bay has more rivers and creeks and anchorages than Florida has Publixes,” I tell Jean, who has come along to crew on the first leg of my trip back to the Chesapeake from St. Petersburg. She listens politely, her legs stretched out languidly on the cockpit cushions.

It’s a late afternoon in late March and chief of onboard security Bindi is stretched out asleep on the foredeck, while her apprentice, Junior Seaman Sammy, scrutinizes a manatee who persists in coming up for air just inside Moment of Zen’s designated exclusion zone. To our north, the busy Saturday Fort Myers boat traffic is zipping up and down Pine Island Sound within sight, but well out of earshot. We are deep in the bay’s pocket, off the Ding Darling Wildlife Area.

But like the manatee, I persist, “Why, I could close my eyes and put a dozen stickers randomly on the map of the Chesapeake and get a series of cruises out of them.”
“That’s ridiculous,” Jean replies.
“You’re on,” I say.
But neither of us moves.
There will be plenty of time for stickers later.

That evening, though, I put my boast to the test. I tear off little bits of blue masking tape and aim for a random distribution, north to south. I close my eyes and begin. Soon, the dogs lose interest. Jean begins quietly flipping through an old New Yorker, looking for cartoons.

“Ta-da!” I say finally and open my eyes. “Not too bad,” I say, seeing that most of them have landed close to the water, though I’ve managed to place one squarely in Poolesville, Md. I move the rest to the nearest piece of navigable water, and step back to see if I can make good on
my boast. 

“Hmm,” I begin. Sammy looks up.
“Hmm,” I repeat. And this time Jean looks up.

“Well, I see you have put your sticky things on the map, but what makes you think you can convince people to go there?” she asks pointedly.

“Because every place on the Chesapeake is interesting in its own way,” I insist. “I just have to explain how it is.” I am definitely getting enthusiastic about this now because all of these are, in fact, great places to cruise. I can’t wait to do these myself this summer.

“See?” I begin, “Let’s look at the northern Bay cruise. . . .”


Upper Bay Cruise from Middle River

Day 1: Middle River to Betterton, 15 miles

If the weather is nice and quiet, even hot, I suggest we begin this cruise by making the 15-mile trip from Middle River across the Bay to the mouth of the Sassafras River and our first destination. The chances are good that we’ll find a nice breeze to cool us off when we drop the anchor off Betterton, once the Bay’s most popular summer resort. Alternatively, we can look for dock space at the town dock. In either case, once ashore we can enjoy a stroll along the bluff and imagine the days when steamboats brought crowds of summer visitors ashore and the bluff was lined with busy hotels and restaurants. None of that, alas, remains.
The upside of Betterton is its convenience to the Bay—only a mile off the main channel—which is also its downside, since ship and boat wakes can shake things up and strong winds and chop can make the night uncomfortable. So, if the Bay begins to kick up, we may want to head upriver to one of my favorite anchorages, Turner Creek. Or if we want a marina, we can find half a dozen good ones farther upriver at Georgetown.

Day 2: Betterton to Gibson Island, 30 miles

Our next stop, Gibson Island, lies about 30 miles down the Bay from Betterton at the mouth of the Magothy River. We’ll have a lovely day of it. Aftersqueezing through the narrow but well-marked entrance to the Magothy, we’ll turn north to trace the western shoreline of Gibson north into Sillery Bay and then across the top through Magothy Narrows into the Inner Harbor. I happen to know there are two excellent anchorages in this very protected spot, and I haven’t decided
yet which I’ll choose for the night.
The first is Eagle Cove, which lies just inside Gibson’s inner sanctum, and the second is Redhouse Cove, all the way inside beyond the Gibson Island
Yacht Club. 
But if the night is hot, or we’re in the mood for a party, we can join the crowd off Dobbins Island. On the other hand, if we want a marina or restaurant, we’ll find some very nice ones along Magothy’s opposite shore.

Day 3: Gibson Island to Gunpowder River, 22 miles

My third blue sticky tape landed right in the middle of the Gunpowder River, which is a good thing because the shoreline is largely occupied by Aberdeen Proving Ground and so is off limits to boaters, as is swimming. It is a good place for a long weekend cruise, because it’s always open on weekends. 
The Gunpowder is pretty shallow, but should be fine for boats with a draft of 4 ½ to 5 feet. The draft on Moment of Zen is just shy of four feet, so you can expect to find me sounding out a nice anchorage on Saltpeter Creek behind Carroll Island or across the river behind Maxwell Point.
The Gunpowder is a good place to end our Middle River cruise, since it’s just a short trip around the corner to get back home.


Middle Bay Cruise from Annapolis (or Solomons)

Day 1: Annapolis to Plaindealing Creek, 30 miles

When I lifted blue sticker number four to find Plaindealing Creek behind it, I was delighted. Plaindealing Creek, if you don’t know it, is a lovely little stream that lies on the north shore of the Tred Avon River, opposite the town of Oxford. It makes a very sweet, quiet anchorage all on its own but also as a private retreat away from, but close to, busy Oxford and Town Creek. 
The first half-mile of Plaindealing has enough depth for most boats, with entry depths of 11 feet, giving way to 9 then 8 then 7 and so forth as you work upstream. You should find 6 feet for at least a mile. Green “1” at the entrance marks the shoal off the western point. I’d give it a good berth, because of the shoal creeping beyond the marker. About three-quarters of a mile inside, there is a nice wide spot with coves on both sides that makes a nice anchorage.
On the trip over from Annapolis, I will also probably chance the capricious Knapps Narrows channel rather than take the longer way around to enter by the Choptank’s mouth. You can make your own choice based on your boat and nerve. Plaindealing, by the way, was apparently named by local Indians for a trading post established there by the plain-dressing, fair-dealing Quakers. 

Day 2: Plaindealing Creek to St. Leonard Creek, 37 miles

Fresh off a relaxing night on Plaindealing Creek, we should probably get an early start for our next destination, St. Leonard Creek on the Patuxent River, a distance of some 37 miles. Yes, I’ve inadvertently given the middle Bay cruisers a lot of ground to cover. But it will be worth it. 
We can come out of the Choptank River and shoot across the Bay to the Patuxent, then follow that river past Solomons and around Point Patience before searching out green “1” at the entrance to St. Leonard Creek, another three miles north. 
Once past green “1”, we can wind up St. Leonard Creek, passing Jefferson Patterson State Park—
a good place to dinghy or kayak, if we have time. The banks become increasingly steep as we work upstream with boathouses poking out among the trees. This is one of the most scenic creeks on the Bay.
There are anchorages close to the mouth (convenient, but lots of wake) and farther up. I like to anchor in Rollins Cove, two miles upstream. There is a picture-perfect cove just inside to starboard with about eight feet. 
On the other hand, I also like to stay at the marina at Vera’s White Sands. The docks are good, and it’s always a pleasure to reminisce about the old times when Vera Freeman was the queen of St. Leonard Creek and her White Sands attracted more boaters than Solomons.

Day 3: St. Leonard Creek to Galesville, 43 miles

I’m setting the alarm for Day Three, because we have a lot of miles ahead of us today, and because
I don’t want to miss dinner, probably at Pirates Cove, in Galesville on the West River. On the other hand, I may dock at Thursday’s Steak and Crab House for dinner and then anchor out in Smith Creek or any of a half-dozen nearby West River anchorages. Once you see it, you’ll get the idea. 
Galesville is a tiny town with a long history in boating. Hartge is a name that still thrills sailors along the Atlantic seaboard, and Galesville is still big a place for one-design racing.
Watch the pointy shoals at the entrance to West and Rhode rivers. They are well marked, but as you know, shoals have a tendency to spread. Once inside, keep straight on, and the markers will lead you straight to Galesville. From there choose your marina or restaurant and enjoy! Depths in front of town are consistently in the sevens and eights.


Upper Lower Bay Cruise from Deltaville

Day 1: Deltaville to Little Wicomico River, 20 miles (from Stingray Point)

Here are three places that rarely make anyone’s cruising list, but, in my opinion, should be right near the top. My only quandary is deciding which way to go first. I would probably begin with the Little Wicomico River, a wonderful place with a slightly scary entrance. There is also a lot of shallow water just inside the jetty. But after that . . . well, it’s like slipping through a worm hole into another time. Workboats still off-load their daily haul at old wharves. The modest homes along the shore still probably still pick up the Ed Sullivan Show on their console television sets. It’s hard to do justice to a place like the Little Wicomico in the short space I’ve got here. But if you’ve never been, do yourself the favor and go. 
My blue sticker landed in the middle of the river, so we have lots of choices for where to spend the night. It could be one of two marinas, Smith Point Marina (804-453-4077) or Cockrell’s Marine Railway (804-453-3560). Both are repositories of a lot of Bay history. But we’ll need to call first to get directions for deepest water, both to their entrance channels, especially Smith Point, and to the Little Wicomico itself. The latter is dredged regularly, but shoals up just as often. As a bonus, the current can run quickly through that narrow passage, so a slack-water timing is not a bad idea.
There are plenty of places to drop anchor, including a very nice spot where Ellyson Creek branches off just before you come to a perfectly charming car ferry. Note that the ferry operates by cable, so be sure not to cross its path until the cable has time to drop.

Day 2: Little Wicomico to Occahannock Creek, 25 miles

Well, Deltaville: I have set you three lovely but challenging stops for your cruise. For our second stop, if you draw much more than five feet, you might want to just squeeze inside Occahannock for the bragging rights and then backtrack either down to Cape Charles or up to Onancock for the night. Or you can drop anchor just inside off of Concord Wharf on the south shore. Alternatively, you can just throw caution to the wind and give it a whirl, because I think you can make it at least to Davis Wharf Marina (757-442-9242) about four miles upriver. I am particularly fond of Davis Wharf, which has fuel and can do repairs of all sorts. Be sure to have a look in the work shed where there is always something interesting in the process of restoration. 
Across the creek from Davis is Morley Wharf, which has a boat ramp and short-term dinghy dock to use if you anchor just beyond Fisher Point. Finally, there is a picture-perfect anchorage in perhaps four feet of water just beyond Shields Cove. Good luck.

Day 3: Occahannock Creek to Stutts Creek, 25 miles

On the third day, we’ll head nearly back to Deltaville before turning off the Piankatank River into Milford Haven. After the Gwynn’s Island Swing Bridge (12-foot clearance; opens on request on channel 13 or 804-725-2853), we’ll continue down Milford Haven to the entrance of Stutts Creek, which is marked by green and red markers “1” and “2”. The Stutts Creek channel then winds a bit but is clearly marked all the way to Mathews Yacht Club, about a mile and a half in.
After the trials of Little Wicomico and the shallow water of Occahannock Creek, Stutts Creek, with six to eight feet, is going to feel like a walk in the park. And it will look like one, too, with widely spaced homes set among groves of trees and sweeping lawns. There’s an anchorage just before Mathews Yacht Club’s docks but I can’t say much because I’ve never anchored here. I’m looking forward to it. And we can all sleep late because it’s a short trip back to Deltaville to end our cruise.


Lower Bay Cruise from Hampton

Day 1: Hampton to Kiptopeke, 20 miles

Hampton, we’re going to have fun with this one. We will have plenty of depth all along the way, but we will want good weather for the first of our stops, Kiptopeke, which is fairly exposed. Assuming the forecast is good, we can zip the 20 miles from the mouth of the Hampton River across the Bay to Kiptopeke, home of the concrete ship graveyard. This singular breakwater of nine half-sunken World War II Liberty ships provides some protection from wind and wake. 
The Liberty ship breakwater has a break approximately in the center, which will serve as our entrance. The water here is at least 20 feet, so the passage will be an easy one.
Once we’re through, we can choose a spot between the ships and Kiptopeke State Park, depending on the wind and boat traffic. The dinghy-accessible park has a swimming area, boat ramps and walkways over the marshes. You may even want to come for the Eastern Shore Birding Festival in October.
Before the Chesapeake Bay Bridge-Tunnel was completed in 1962, all traffic went by ferry from Kiptopeke to Virginia Beach.

Day 2: Kiptopeke to Little Creek, 17 miles

After a morning dinghy trip to the park, we can pull up the anchor and take aim for our next stop, Little Creek. The two destinations couldn’t be more different. They are also among the Bay’s most unusual. While Kiptopeke is all broad views and sandy beaches, Little Creek feels almost claustrophobic, with the Navy’s Little Creek Amphibious Base on one shore and more than half a dozen marinas tightly packed along the other. I find it completely fascinating.
The entrance is through twin jetties marked by red and green “3” and “4”. As soon as we get
inside, we’ll need to make a sharp turn to starboard to stay clear of the restricted Navy base waters. Immediately, the long line of marinas begins. I have stayed at the first two, Bay Point (757-362-8432) and Little Creek (757-362-3600), but this time I think I want to go nearly to the end to Cobbs Marina (757-588-5401), one of two on the south side of the creek. Eventually, I’ll try them all. The choice is yours.

Day 3: Little Creek to Cobham Bay, 37 miles

On the third day of our cruise, we’ll awake to Reveille, slip off the lines and set out for the James River and our final destination, Cobham Bay. We can cut carefully across Willoughby Bank to join the main shipping channel about three miles east of the Hampton tunnel. From there, we’ll follow the channel under the James River Bridge (closed clearance 60 feet; if you need more, it will open on request). Another seven miles and we’ll come to Burwell Bay, home of the Navy Reserve Fleet, or Ghost Fleet. Once the resting place for dozens of mothballed ships, it is now largely depopulated. After Burwell Bay, the James loops around Hog Island and then opens out to the south to form large and impressive Cobham Bay. Straight ahead of us is Jamestown Island.
My favorite anchorage here is at the bottom, off Chippokes Plantation State Park. There is good protection from the south and pretty good cover from the east and west. And, there is shore access at Chippokes Park, with good water close to shore. If it is a still night, you might choose to drop anchor off the monument on Jamestown Island. But, you might also find the wake from the Jamestown-Scotland ferries a trial.



Well, there you have it. A suite of cruises selected with closed eyes and blue sticky tape while anchored one night in Florida. There’s not a dud in the lot.