Chesapeake Bay boating guide

Chesapeake Bay Boating Guide: Cruising America’s Largest Estuary

Written by Zuzana Prochazka
November 29, 2023

Last Updated on November 29, 2023 by Boatsetter Team

Cruising the Chesapeake Bay by boat can be a lifetime endeavor since there is so much to see and do in America’s largest estuary. The bay is nearly 200 miles long and anywhere from 3 to 30 miles wide. Its shoreline is over 11,000 miles, and about half of the bay’s 8,100 square miles of watery surface is in Maryland and half in Virginia. 

The Bay spills from the Susquehanna River source in the north down to the Atlantic near Norfolk, Virginia leaving thousands of anchorages and 150 rivers to explore! In our Chesapeake Bay Boating Guide, we’ll explore:

  • Things to do  
  • Best time of year to boat on Chesapeake Bay  
  • What to look out for 
  • Pro tip!

Explore boats & on-water experiences in Chesapeake, VA


Things to do at Chesapeake Bay

St. Michaels

Perhaps the best-known town on the Bay is Annapolis with its renowned sailboat show, the prestigious Naval Academy, countless museums, and dozens of quaint eateries. It makes a great place from which to launch an exploration. 

Approximately 25 miles southeast of Annapolis lies St. Michaels, a seaside resort on Maryland’s eastern shore. St. Michaels is a must-see for history buffs, crab lovers, and amateur photographers looking for inspiration because this place never takes a bad picture. 

In the summer, the population of St. Michaels swells beyond its 1,500 permanent residents, and getting a guest dock is like winning the lottery so you won’t be alone anchoring out on the Miles River in 15-30 feet of water. Visit the outstanding Chesapeake Bay Maritime Museum with its 18 acres of exhibits and restored boats on display.  

Farther south around Tilghman Island and up the Tred Avon River is Oxford, one of Maryland’s oldest towns. There are lots of wonderful bistros and restaurants like Schooners and The Masthead but save room for dessert because if you leave Oxford without stopping at Scottish Highland Creamery, you’d have missed possibly the entire reason to be here. This ice cream shop is hardly more than a window front but serves homemade frozen treats to die for.

Solomons Island

Cross the bay and head down to Solomons Island, another former boatbuilding and seafood packing town that today is a tourist magnet. Jutting out between Back Creek and the Patuxent River, Solomons is connected to the mainland by a long causeway. 

Less than 1 ½ miles long and in parts just the width of a two-lane road, the island has a long wooden boardwalk that takes you up to the Calvert Marine Museum with its Drum Point screwpile lighthouse and narrated tours on an 1899 bugeye boat. In the 1880s, more than 500 locally built boats made up the Solomons fishing fleet and by the 1930s, the town specialized in building wooden pleasure yachts.  

At the bottom of the Bay, you’ll find Norfolk, which is part of the largest shipping port on the East Coast. Naval vessels, commercial ships, and recreational boats all share the same waters, and Mile Marker Zero, the official beginning of the Intercoastal Waterway (ICW), marks the beginning of the 1,200-mile journey to Florida and beyond. 

For more than two centuries, Norfolk has been a Navy town, and today, you can still tour the naval base. A must-visit is the Nauticus, a multi-level maritime museum designed to educate as well as entertain. The USS Wisconsin is berthed next door and dwarfs the surrounding buildings. It was a veteran of three wars and the last battleship built for the U.S. Navy. 


Best time of year to boat on Chesapeake Bay

Chesapeake Bay best time to visit

Summers can be sweltering and winters freezing but the shoulder seasons of spring and fall are phenomenal. In April to May and September to October, the crowds are small, and the weather is usually perfect for boating. 


What to look out for

The Chesapeake is a fairly protected body of water, but it can get boisterous. Northerly winter storms kick up large square waves that build the entire length of the shallow Bay and become quite serious in the southern parts. Also, it’s very easy to wrap a prop on one of the ubiquitous crab pots or ground in the shallows. Keep a good lookout and rest easy knowing that the Bay is nearly all soft mud which shouldn’t cause too much damage to your keel.

Pro tip: If this is your first time on a boat or have little experience, we strongly recommend booking a boat with a USCG-certified captain


Pro tip: Rent a boat for your Chesapeake Bay boat trip!

The Chesapeake Bay is a unique place begging to be explored by boat. It’s also great for a corporate event, a birthday party, a sailing regatta or a romantic sunset outing. Book a boat with a USCG-certified captain for a local guide, or take the helm on a bareboat—Find all options on the peer-to-peer (P2P) boat rental marketplace. 

There are dozens of boat rentals in the Boatsetter fleet with locations from Baltimore, to Annapolis and Deltaville to Norfolk. And if you’re in town for the boat show, staying on a boat will save you a bundle due to skyrocketing hotel prices.


You’ll be back

The vast Chesapeake Bay can’t be seen in a day, a week, or even a month. You’ll want to come back again and again to stay in the towns, fish the rich waters, and watch sunsets from secluded anchorages. Once is definitely not enough. 


About us 

Boatsetter is the go-to app for boat rentals and on-water experiences. Whatever the adventure, we’ve got a boat for that—Set sail, start the party, go yachting, make your trophy catch, and hone your watersports skills! Download the Boatsetter app (App Store | Google Play). Make sure to follow @boatsetter on Instagram, and tag us in all your boat day pictures for the chance to be featured. 


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