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 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 Bay 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. 

NOTE:  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. 

Read the full guide including Navigation Notes, Tides & Currents, Weather and more at BoatLifeAcademy.com.

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