Boater’s Guide to Chesapeake Bay 

While you can get to major cities such as Norfolk, Annapolis, Washington DC, and Baltimore during a Chesapeake Bay cruise, the charm lies in its laid-back, country-lane feel. In the Chesapeake Bay, you can play on a sandbar, taste fresh catch, visit the capital city, spot deer on a country lane, watch Navy ships in Norfolk, visit museums, and swing at anchor in a solitary anchorage.

Cruising in the Chesapeake Bay affords access to diverse towns and cities, as well as protected waters, quiet anchorage gunkholes, and various other recreational opportunities. 

It’s not all sunshine and crab feasts, of course. This shallow bay can get surprisingly choppy in adverse conditions. The quiet anchorages are often way off the Bay and can add many hours to your travel day. Crab pots and fishing stakes can create navigation hazards. 

Chesapeake Bay Boating Overview

The Chesapeake Bay is one of the world’s most expansive estuaries. It’s fed by several major rivers, including the Susquehanna out of Pennsylvania, the mighty Potomac (navigable to the nation’s capital), and the Rappahannock — the largest river in Virginia. In addition to these big waters, there are hundreds of smaller rivers and creeks along the Bay’s shores.

The central Bay is fairly exposed and builds up a chop on a windy day. The protected anchorages are nearly always many miles off the Bay, meaning that slow boats can expect an hour or more of navigating at the beginning and end of each day’s travels.

Chesapeake Cruising Conditions

The Bay has three distinct regions: the Upper, Middle, and Lower Bays. Each region gets progressively wider and more open as you travel south. The Upper Bay is like traveling on a very broad river — you can see both shores, and it’s only a few miles wide. On the other hand, the Lower Bay feels like open water. You cannot see the Eastern Shore from the mainland and vice versa. Another change you experience as you travel south is the land’s topography: Virginia is significantly flatter than Maryland.

Chesapeake Bay Marinas and Anchorages

There are countless marinas on the Bay and probably thousands of potential anchorages. 

Marinas cater to either locals or transients and often both. 

A Bay marina ‘local’ nearly always lives a few hours away by car and keeps their boat for weekends or holidays. Marinas in coastal Virginia are full of boats with homeports like Richmond, Charlotte, and places even farther afield. 

Many of these marinas have an active club atmosphere for their slipholders. Marina amenities range from great rates to amazing locations with swimming pools and clubhouses. These marinas sell the weekend getaway lifestyle and club as much as they sell slips. 

Of course, these marinas welcome transient boaters as well. The marinas that see the most transient boats are near the north-south middle-of-the-Bay route. These will typically have the highest slip and fuel prices, too. 

Boaters should be aware that fixed docks are the norm in the Bay since tides are moderate (usually two to three feet). Short finger piers are also typical, making docking a bit challenging for short-handed crews. Be ready to throw spring lines on the outside pilings as you approach because the dock hands can’t help with anything outside of the main dock. Floating docks are not unheard of, but they are rarer than in other places and often priced accordingly.

The Bay is a special paradise for boaters who like to spend quiet nights on anchor. From open roadsteads to gunk holes as cozy as your draft allows, there’s something for every boater. 

What's even better? Anchoring overnight is normal here and not frowned upon by the locals. 

Once, when anchored up a cozy creek for a passing tropical storm, friendly homeowners boated over and gifted us a basket of fresh flowers and homegrown heirloom tomatoes from their garden. They went on to invite us to use their dock. 

That just does not happen in Florida. 

The primary problem with anchoring in the Chesapeake is not a lack of places to go but the temperatures. Summers are still and hot, and a muggy night at anchor can be awful. After several seasons, we’ve learned to get a dock and run the AC from June through mid-September.

The Bay bottom is nearly always a sticky, stinky mud that is great for anchoring. In areas where the mud is soft and gooey, you might have to allow time for your anchor to sink down and penetrate the bottom. Some areas have some sand, and you might encounter some weed as well. Overall, we’ve found the best anchors for the Chesapeake to be claw or plow types that scoop into the bottom.

Moorings are less prevalent in the Bay than in New England and Florida. Only Annapolis, Georgetown, and Solomons Island in Maryland have moorings, but these places also have plenty of other places to anchor. Even private moorings are relatively rare here. 

ChesBay Navigation Notes

If you’re moving north to south (not sightseeing), there are a few overnight stops that most boaters seem to repeat. Each stop is a day’s cruise from the last, and each has marina, anchorage, and fuel options.

• Baltimore, MD
• Annapolis, MD
• Solomons Island, MD
• Deltaville, VA
• Hampton, VA
• Norfolk, VA

Ship traffic navigates the “ship channel,” which passes over the tunnel part of the Chesapeake Bay Bridge Tunnel and then northbound to Baltimore. There is a large anchorage south of Cape Charles on the Eastern Shore where ships wait for pilots. In the Lower Bay, it’s easy to cross the channel quickly and have little or no interaction with big ships. In the Upper and Middle Bays, you operate closer to ships more often. Ships also regularly approach the Bay from the north through the C&D Canal that connects Chesapeake and Delaware Bays.

Chesapeake Bay is shallow. USGS states that the Bay averages 21 feet deep, and nearly a quarter of it is shallower than 6 feet. Numerous shoals stick out from peninsulas (locally called “necks”), often necessitating miles of trekking by water to move from one river to the next. 

Thousands of rivers and streams feed into Chesapeake Bay. Because the bay is protected on all sides by land, conditions are often good for sailing or motoring. However, the Bay’s shallowness means a stiff chop can pick up quickly in adverse weather. 

Tides and Currents on the Bay

Most of the Chesapeake Bay has average lunar tides between two and three feet, and spring and neap tides are between three and four feet. 

However, the Bay is subject to wind-driven tides. Water levels drop quickly during north winds and rise during south winds. East or west winds will pile water up on the opposite shore, especially up the rivers and creeks. If navigating after periods of extended winds, you must add a fudge factor since the water could be lower than you expect.

Currents are minimal unless you’re trying to go in the opposite direction. Then, they are oddly strong and against you. With so many major rivers emptying in the Bay, it’s nearly always slower going northbound than southbound. But, in all seriousness, currents are rarely more than 1 knot and generally between 0.3 and 0.5 knots. The farther north you are, or the larger the river you are on, the stronger the currents you will experience. 

The one important exception is the area at the mouth of the Potomac River. The confluence of the Upper Bay and Potomac, which is roughly 10 miles wide between Point Lookout, MD, and Smith Point, VA, plus the dramatic changes in depths around the area, make for an unpredictable and often surprising mix of wind, current, and nasty choppy waves. It’s best to avoid transits in this area when wind opposes current — but that can be difficult to pin down. Better year, follow the Eastern Shore (thereby avoiding the open waters of the Potomac crossing) or transit on very calm days. If the wind is up, plan for rough conditions during this transit.

Chesapeake Bay Boating Weather

Boating season in the Bay is during the summer, but it’s significantly longer than in New England. The Bay seldom experiences thick ice, and many locals consider boating in the Lower Bay a four-season affair with the right boat.

Most cruisers visit Chesapeake Bay in the summer. One big reason is that it’s far enough north to be considered “safe” by many insurance companies during hurricane season (June 1 through Nov 30). Boaters are pretty evenly split between those that get a dock to liveaboard over the summer, those that continue cruising on the Bay or farther north, and those that haul the boat to do work or put it in storage until their next season heading south. 

The Bay does experience hurricanes, though — sometimes strong ones. Thankfully, they are rare. However, tropical storms and remnants come through each year as systems work their way north after both Gulf and Carolina landfalls. These storms bring strong, gusty winds, high storm tides, and flooding. Plenty of damage is still done, so don’t let your guard down just because you’re outside your insurance company’s arbitrary box. 

If tropical weather threatens, there are many creeks and rivers with protection to hide in. There are also many boatyards that will be able to haul you ahead of a storm. Unlike Florida, hurricane hauls are affordable, and you do not have to be part of a pre-paid program to be hauled. It’s also easy enough to move farther north or south to get out of the storm’s immediate path (or to at least find a boatyard with availability). 

During the summer, the Bay can be muggy and windless. Airmass thunderstorms build up throughout the day over the mainland and then drift eastward into the Bay. These storms can be violent and quick-building, seeming to come out of nowhere with gust fronts up to 70 knots and lots of lightning. Mariners should pay attention to local weather advisories and seek a protected anchorage before a forecast thunderstorm.

The shoulder seasons of spring and fall are pleasant and long in the Bay. Cold fronts affect the area more often and earlier/later than in places farther south, but there are still plenty of warm, sunny days. The wind picks up for sailing, and in the fall, the water remains warm enough for swimming well into October.

Weather forecasts for the Bay are often varied and changeable. The area’s location near the shifting upper-level Jet Stream means that a small change in upper-level winds could spell the difference between a warm and sunny week and a cold, damp, drizzly week. In the fall, I’ve lost count of the times I’ve woken up to what was supposed to be a sunny day to find it overcast and cool. Dense fog can also surprise you some autumn mornings, but it usually burns off before noon.

Winter on Chesapeake Bay

Winters are quiet on the Bay, and you can keep your boat in the water year-round in most places as long as you have a winterization plan. Most boats haul out for the season, but the farther south you go, the more boats you’ll find over-wintering in the water. 

The number of small creeks that freeze over decreases as you head south. Temperatures hover around freezing in January and February, and you may even see a few snow days. North of Annapolis, most creeks will freeze over, but major rivers and the Bay are nearly always passable. In the Lower Bay, thin ice on small creeks rarely lasts more than a day or two. Most marinas have bubblers for those particularly bad winters.

You can enjoy winter boating by un-winterizing and re-winterizing after an outing. Winter has special treats for hardy sailors, including wind — something that’s in short supply here during the summer. Pelagic species like gannets come into the Bay during the winter, and you’ll probably have the marinas and anchorages all to yourself.

If you plan to cruise the Bay in winter, be aware that marinas usually turn off the dock water, pump-outs, and maybe the restrooms. Many marina-based businesses may close for the season, but there are enough full-time landlubber types around that most restaurants and shops remain open.

If you are living aboard in the winter, you may be able to run your reverse-cycle heating and take the boat out for a spin on mild days — at least until the water temperature dips below 40ºF. Locals favor other heating options, like diesel, propane, electric, or solid fuel. Whatever you do, you must be ready for an occasional ice or snowstorm that could knock out power to rural areas for a few days. 

Special Notes About Boating in Chesapeake Bay

The watermen of Chesapeake Bay work all year to supply the world with oysters, rockfish, and blue crabs. You will see them working from their distinctive Chesapeake Deadrises and outboard skiffs wherever you go. And, wherever you go, you will run into their fishing gear. Crab pots are the number one item of concern for most boaters.

If you look closely at the chart, you’ll notice fishing gear areas marked on the outside of navigation channels. There’s no reason not to transit these areas, but expect to dodge a lot of crab pots here. If you want less (not none, none doesn’t happen), stick to the channel outside those dashed fishing gear zones. 

Another thing to be aware of while swimming is the presence of stinging nettles, a brackish-water jellyfish that can be numerous and annoying. They are densest at certain salinities and temperatures, so how many you see waxes and wanes over the summer. They peak sometime in July. There’s even a nettle probability forecast published by some Bay weather bouy stations. 

For most, a nettle sting isn’t as bad as it sounds. There are certainly biting flies that are more painful. Most people react to the nettles like they do to mosquito bites. You still wouldn’t want to get entangled in a big one and stung multiple times, though. And, of course, some people have a much more serious reaction to them. 

One of our biggest problems with the nettles is that they foul our air conditioner intake strainer. During the peak of nettle season — which happens to be the hottest days of summer — we’ll have to clean the filter out every day to make sure the system doesn’t overheat. It’s a nasty job. We’ve also had some very large eels get stuck in our AC intake, but that’s a story for another day. 

Oh, and about those flies. Flies can be numerous at times in the Bay. A swarm of regular house flies once beset upon us in the middle of the Potomac. Thankfully, they didn’t bite. But there were so many of the annoying buggers that the dog and I were ready to abandon ship and give them command. Thankfully, Lucy kept her head, and we still have our boat. 

Boating With Pets on Chesapeake Bay

The Bay is one of the more friendly places to take your pet boating. Dogs will love roaming the occasional sandy island or low-tide beach, and the area is one of the pet-friendliest we’ve ever visited. It’s very common for outdoor restaurants in Maryland to have doggie menus, offering chopped burger patties, grilled chicken, or even pasta and meatballs (Ava’s in St. Michaels).

When gunk-holing in creeks lined with residential homes, it can be challenging to find places to land the dinghy for a walk. We favor places that have low-tide sandy beaches or sandbars. We’ve also learned to look for boat ramps, which are usually at the end of county roads and are very quiet. They’re usually marked on Active Captain.

Chesapeake Bay Boating Places of Interest

Major Ports and Cruiser Hangouts

• Norfolk/Portsmouth, VA
• Hampton, VA
• Deltaville, VA
• Solomons Island, MD
• Annapolis/Edgewater, MD
• Baltimore, MD

Cute Places You Ought to Visit

• Yorktown, VA
• Cape Charles, VA
• Onancock, VA
• Urbanna, VA
• Tangier Island, VA
• St. Michaels, MD
• Cambridge, MD
• Havre de Grace, MD

Annapolis Power and Sail Boat Shows

The pinnacle Chesapeake boating event is the Power and Sailboat Shows in Annapolis every October. It’s one of the largest boat shows in the nation and is well attended by boaters from every wave of life. Each show is on a different weekend, so you don’t have to worry about rubbing shoulders with stink potters or blow boaters. Whichever puts you off will be there on a different weekend.

Many cruisers base their schedules on the show, as its timing is convenient for the southbound migration. When the show is over, a flotilla heads for Norfolk to begin their treks down the ICW or around Hatteras.

For those looking to avoid crowds, the boat show is not the right weekend to visit Annapolis. The entire downtown waterfront, known as Ego Alley, is closed off and converted with floating docks for the show. The moorings balls in town are in short supply. 

Places to Get Boat Work Done (Or Do Boat Work)

The Bay has an enormous number of marine service providers. Many are geared to serve local boaters, but as more and more seasonal cruisers have ‘discovered’ the Bay, many are now focusing on providing services to transient boaters. One of the wonderful things about the Bay is that there are still relatively inexpensive DIY and liveaboard boatyards available—things that have become very hard to find in New England and Florida.

While boatyards are spread throughout the Bay, several hubs are known for having multiple yards and many services. These include Deltaville, VA, Solomons Island, MD, and Annapolis, MD. Generally, yards (and marinas) get more expensive the farther north you travel, with the highest prices around the Annapolis area. 

Notably, many Chesapeake boatyards have upgraded their facilities to be able to haul wide-beam catamarans. Catamaran boatyard in the Chesapeake include (be sure to call and confirm your beam):

• Georgetown Yacht Basin, Georgetown, MD
• Worton Cove, Chestertown, MD
• Long Cove Marina, Rock Hall, MD
• Dennis Point Marina, Dryden, MD
• Bay Bridge Marina, Stevensville, MD
• Port Annapolis Marina, Annapolis, MD
• Pier 7 Marina, Edgewater, MD
• Zahnisers & Washburns, Solomons, MD
• Yankee Point, Lancaster, VA
• Stingray Point Boatworks & Deltaville Boatyard, Deltavilla, VA
• Zimmerman Marine, Mathews, VA
• Cape Charles Yacht Center, Cape Charles, VA
• Cobb’s, Norfolk, VA
• Atlantic Yacht Basin, Norfolk/Chesapeake, VA

Chesapeake Bay Area Resources, Guides, and More Information

Charts are fairly accurate for the Bay, and most NOAA and Navonics charts show similar features. Anchorage and marina reviews are available from Waterway Guide or Active Captain. Some creeks are sounded with USACE depth surveys, available on the AquaMap app with the Master subscription. 

US Army Corps Hydro Surveys for Chesapeake Bay

Knowledge Base Article: Dealing with Fishing Gear

🛒 Buy on Amazon — Waterway Guide Chesapeake Bay edition

Spin Sheet and Prop Talk Magazines (Free at all marinas in the area)

Local Facebook Groups:
(There are many more, including ones more specifically directed toward fishing or motorboats and one’s hyperlocalized by town or even specific marina clubs/slipholders.)

• Upper Chesapeake Recreational Boaters
• Middle Chesapeake Bay Sailing
• Lower Chesapeake Bay Sailing