A Cruise on the Chesapeake – What To Know

March 15th, 2024 by team

by B.J. Porter (Contributing Editor)

The Chesapeake Bay is the largest estuary in the U.S. and also has some of the nicest cruising and sailing waters on the east coast. It’s big – 200 miles from end to end, and thirty miles wide at its widest. Over 150 rivers and streams feed the Chesapeake watershed, and the bay touches six states.

On the eastern and western shores, you’ll find everything from big cities to tiny fishing villages. Beaches and bars, nightlife, fine dining, and quiet nature hikes are all within a day’s sail of most anchorages. And there are hundreds of anchorages and miles of streams and inlets to go gunkholing and explore.

We can’t cover it all in a short blog post, but we can give you a taste of some things to think about. Whether you’re passing through, coming for a visit on your boat, or chartering, there’s plenty to see and do. You could spend months exploring every tributary and inlet.

Chesapeake geography, layout and climate

The bay splits up into roughly three sections: the upper, middle, and lower bay. The upper bay is most populous, with major cities and towns like Baltimore, Annapolis, and Havre-de-Grace. The middle bay on the eastern shore is where you find more quaint towns, beautiful beaches, and lovely landscapes. The lower bay has even more remote islands and villages on the eastern shore, and the more developed Virginia shore on to the west.

The bay initially formed from a large meteor strike some 35 millions ago. About 10,000 years ago, rising sea levels flooded the Susquehanna River valley to form the bay as we know it. It’s a fairly shallow bay, with an average depth of only twenty-one feet, with many inlets and tributaries perfect for shallow-draft “gunkholing.”

The water is brackish, tending towards more salinity as you move south towards the ocean and the lower bay. The estuary is home to a wide variety of marine life, both as permanent residents and migratory visitors. Though it is protected water, the bay is wide enough and long enough to build up serious fetch and tricky waves in bad weather.

The climate is “humid subtropical,” with hot humid summers and milder winters. Boaters are on the water year round, though the peak seasons are outside of winter. August is hot with light winds, and spring and fall are popular shoulder seasons for floral blooms, foliage, and milder weather with more breeze.

Cruising on the Bay

Navigation on the bay is fairly easy, since it’s not so wide that you often lose sight of land. The water can be shallow, especially closer to shore and in the various streams and inlets. Take special care to look for crab pots near steam and river mouths. If you pick one up, these crab pots can be quite difficult to get off since they are often anchored with steel cables.

While there are plenty of marinas on the bay, be ready to anchor out in some of the smaller inlets and coves. You’ll need reservations in a lot of places, and moorings aren’t as common as slips.

In the upper bay, you’ll have plenty of access to restaurants, supplies, and groceries with little more than a walk or quick cab ride. As you head down the bay and across to the eastern shore, make sure you’ve got more of what you may need on hand.

Food and Culture

Fishing and seafood has been a mainstay of the Chesapeake regional economy since settlers first arrived, and all over the bay you’ll find excellent fresh seafood. While many types of fish are available, crabs and oysters are two regional specialties seafood lovers should seek. “Crab houses” are everywhere, but check reviews to find where the locals go.

Another regional specialty is the Smith Island Cake, available all over the bay area. Of course, you can get them on Smith Island! It’s a layer cake made with eight to thirteen very thin layers of yellow cake and a rich chocolate frosting. It’s almost ubiquitous on dessert menus, and worth trying at least once.

Throughout the boating season, there are at least a dozen seafood festivals around the bay. With so many waterfront venues, you’ll also find art shows, live music, and other fairs and festivals, so check a schedule before you come so you time your visits well.

Must See Destinations

We can’t cover all the fantastic anchorages and coves you can drop your anchor, but if you’re looking for a quiet night on the hook, you can find a spot almost anywhere up a stream or side river. But here are some well-known destinations that every visitor should consider.

Upper Bay

The upper bay is the busiest part of the bay. It’s the best place to pick up supplies and food, and has the most services and amenities. Most charters will start and end in the upper bay.


The Inner Harbor is a destination and of itself, with all the attractions of a major coastal city. From your slip, you can do everything from seeing museums and aquariums, grabbing a fantastic meal, or even taking in a ball game. Reservations are a good idea, as anchoring is very limited and holding is poor.


Annapolis is a sailing town, with lots of boating services and a thriving waterfront. It’s also a former capitol of the U.S., and a walk around the historic downtown and the Naval Academy is always interesting. You’ll find great places to eat or have a drink, and many interesting shops. The city has numerous first-come moorings in several spots, and you can anchor off the town or in a few spots up the rivers. The boat show in October is a huge draw, but moorings and slips are in high demand since the show takes over most of the downtown waterfront.

Rock Hall

This fishing town on the eastern shore, this charming stop, has over a dozen marinas and beautiful scenery on the water and off. Check out some restaurants in town for the best seafood and crabs, and you’ll find live music on weekends. There are events throughout the season, like the Waterman’s Day festival in July, a fun show of boating skills and talent celebrating those who make their livelihoods on the bay.

Middle Bay

You won’t go wrong gunkholing on either side of the middle bay, but many of the highlights are on the eastern shore.

Wye River / Wye Island

The Wyle Island Natural Resource Management Area covers most of Wye Island on the Wye River. You can anchor in the river, and come ashore on the island to hike, picnic, birdwatch, and fish. It’s a peaceful spot, where you may see bald eagles, heron, and many other types of wildlife.

St. Michael’s

St. Michael’s is the postcard town for the eastern shore. With several marinas, launch service and a nice anchorage, it’s approachable and fun. Be sure to take in the Chesapeake Bay Maritime Museum and plan for a meal on shore. Bring your camera, and prepare to anchor if you don’t have a reservation because guest slips fill quickly in the summer.


A little further south, you’ll find one of Maryland’s oldest towns. European settlers lived in Oxford by 1859, before Annapolis or Baltimore. From Oxford you can explore the Choptank and Tred Avon rivers, and spend time on shore enjoying the historic scenery and taking in a delightful meal.

Solomon’s Island

At the mouth of the Patuxent River on the western shore, Solomon’s is a popular destination for tourists arriving by car or boat. It was a center for boatbuilding and commercial fishing. Visit the Calvert Museum and the see the Drum Point screwpile lighthouse, and pick one of the fabulous restaurants for dinner. A little north of Solomon’s, children will love fossil hunting on the beach at Calvert Cliff’s State Park.

Lower Bay

At the furthest end of the bay near the opening, Norfolk is a major port at the mouth of the bay. Hampton also has marinas and facilities, and along the way stops like Deltaville are nice to duck in for a night. You can also explore the Potomac. On the eastern shore, tricky currents and shallows surround some islands, so take extra care in your approaches.

Smith Island

This small cluster of islands has a permanent population of only 200, and the primary focus is fishing. It is not reachable by any road or bridge and has no airport. It’s a pretty isolated community, but open and welcoming to visitors. Almost everyone gets around on golf carts, bicycles, or on foot. You’ll not find more knowledge about crabs anywhere, from catching them to cooking them. And after you try the crabs, get the most authentic Smith Island Cake you can find, right on the island where they invented it.


Another small community of watermen, Tangier, island is a little larger than Smith Island with a population over 400. They claim to be the softshell crab capital of the world, where you’ll find the best softshell crabs and crab cakes on the bay. They’re also known for oysters. This island is another step back in time, with loads of quiet, natural beauty.

Cape Charles

This Virginia town also has a rich history, with over 500 buildings dating back to its founding in the late 19th century. Enjoy a mix of architectural styles on a walk through town. Downtown has restaurants, a brewery, gourmet shops, and of course, top rate fresh seafood restaurants. Cape Charles also boasts pristine beaches, sand dunes, and several nature preserves.

Your Cruise Plan

Don’t see it all in a week; you can spend months on the Chesapeake and still find new things. Leave time to explore, because a single night in some places may not be enough. The good news is that while the bay is large, there are few destinations that require long sails to get between. You can hop up and down the bay with a few hours of lovely sailing and be settled in and exploring with plenty of daylight left. Bring your camera, nice binoculars, and a very good appetite!

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