Chesapeake Bay Cruising
Our Chesapeake Bay Cruising section features insights from boaters and liveaboards; tips and stories on cruising the Chesapeake Bay, Great Loop, and Intracoastal Waterway (ICW); along with travelogues from destinations off the Bay and expert tips about boat maintenance and safety. For charter vacation stories visit our powerboat chartering section. And find more DIY articles in our How-To section.
February 5, 2026
Editor’s Note: If you missed Part One, you can read it here. Last month the author covered the
January 27, 2026
Since October 2022, at least six professional and experienced Chesapeake Bay watermen have died on the water, prompting
January 14, 2026
Yes, we are boaters. That means we have a boat or boats, had a boat, lust after a boat, or are “between” boats. You pick.
January 5, 2026
There’s an ancient Latin proverb that says, “audentes Fortuna iuvat:” fortune favors the bold—an idiom engraved on my watch.
December 21, 2025
From time to time I ponder existential questions, like “why is there air?” and “how much deeper would the ocean be if it didn’t have so many sponges?” I even wonder how my life would be different i
December 10, 2025
Each year, hundreds of people are injured, maimed, or killed as result of boat propeller strikes.
November 25, 2025
“The two happiest days for a boat owner are the day you buy a boat and the day that you sell the boat.” I truly understand that old adage but
November 19, 2025
David Sites, the top-scoring
November 12, 2025
Ok, yes, we know you are probably not going to cruise your boat from the Chesapeake Bay to the Pacific Northwest (PNW).
November 3, 2025
In every good story there is an element of suspense, adventure, or mystery. Unfortunately, this story doesn’t have any of those things in it. The trip up the
October 30, 2025
SpinSheet Century Club member Jim Townsend logged 100 days on the water last year by paddling and sailing.
October 13, 2025
Cruising the Chesapeake Bay is never just about getting from one harbor to another—it’s about savoring the small
September 22, 2025
TrawlerFest Baltimore is THE show for cruising enthusiasts, with a wide selection of seminars and also an in-water boat show and social activities.
September 22, 2025
For the fourth time in seven years, a group of like-minded friends rallied their boats and cruised out of Annapolis to the
September 17, 2025
The Chesapeake Bay offers boaters almost unending enjoyment along its thousands of miles of shoreline—the land of pleasant living. But during August it can be hot, humid, and full of jellyfish.
August 27, 2025
We just spent a week cruising the Upper Chesapeake with my boating group, and I started to think about the benefits of having experienced boating friends.
August 19, 2025
As readers of PropTalk know, the Chesapeake Bay offers some of the best cruising grounds in the world.
August 5, 2025
Drew Mutch and Michael-Anne Ashford, formerly of Severna Park, MD, live on Back Creek aboard their Kadey-Krogen 48 Whaleback Escape Plan.