Cruising Ideas for Boaters on the Chesapeake Bay

Why, how, and where to cruise on the Chesapeake Bay... and have more fun doing it!

When cruising the Chesapeake Bay boaters will find welcoming waterfronts and marinas that host transient boaters as well as year-round slip holders. The Bay is beloved by cruisers of all stripes due to its many quaint waterfront towns, rich maritime history, quiet coves with beautiful anchorages, and metropolitan areas with restaurants, museums, and music venues. You could spend years cruising and exploring the Chesapeake by boat, and many sailors and powerboaters have done just that. Here we provide a round-up of cruising itinerary suggestions that include what to see and do in some of the most popular cruising destinations. It's created by boaters, for boaters. Slip the lines and enjoy...

Cruising oasis Herrington Harbour
Photo of Herrington Harbour Marina Resorts, courtesy of Herrington Harbour/Facebook

Cruising to the Upper Bay

North of the Bay Bridge, the Bay's width is a bit more narrow, and the water has lower salinity. Here the mouth of the Susquehanna River flows into the Bay's most northern reaches. The western shore of the Upper Bay is home to Baltimore and nearly 3 million people, while the more rural eastern side is home to several wide-mouth rivers and a slower pace for cruisers looking to get away from it all. Here are five articles with ideas to help plan your next trip to the Northern Bay.

The Secret Charms of Upper Bay Cruising 

A Five Day Sailing Cruise Heading North From Annapolis

The Bay Starts Here: Northern Chesapeake Bay Locations

Four Days Cruising the Chesapeake Bay North From the South River

Cruising the Upper Bay: Patapsco to Gun Powder River

cruising to a beautiful sunset
Photo courtesy of Bowleys Marina/Facebook

Cruising in the Middle Bay

Home to Annapolis, Kent Narrows and Kent Island, the Eastern Bay, St. Michaels, Oxford, Solomons, and with so many other terrific places to dock, dine, and play, the Middle Bay is ideal for cruising. Here are five articles to help you plan your trip.

Take Four Days To Cruise the Middle Bay

Cruising the Middle Bay: Annapolis and the South River

10 Things To Do in St. Michaels

Slow Down and Enjoy the Oxford Way of Life

What To See and Do When Boating to Cambridge, Maryland

A marina with a city in the background
Are you looking for an urban marina or something more remote? You'll find both on the Chesapeake.

Cruising to the Lower Bay

As you travel south, the Bay widens, the water is saltier, and naval ships and commercial traffic are nearby. Welcome to the Lower Bay. Charming, remote spots with beautiful sunsets beckon cruisers to Virginia's Eastern Shore, while on the Western Shore boaters can jump into history and city life in the towns of Norfolk and Hampton Roads. Here are five articles about cruising on the Lower Bay.

Cruising the Rappahannock Mini-Loop

See the Bay: Onancock, VA

Southern Bay Sailing Destinations

Southern Bay Destinations

See The Bay: Visiting Norfolk by Water

boats in Oxford, Maryland
Slow down and enjoy the Oxford way of life. Photo courtesy of Campbell's Boatyards

More Cruising Articles

If all those helpful links above were not enough, here are two more articles about cruising on the Chesapeake Bay.

Safety Tips for Overnight Cruising

Chesapeake Bay Cruising Itineraries for Sailors