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.
March 11, 2026
You know it has been a cold winter when you walk out the door to a day that is 37 degrees with som
March 6, 2026
Raeyane Farrell and Bill Cabrall, Chesapeake sailors and Annapolitans, had dreams of completing the Great Loop and decid
March 4, 2026
For many Chesapeake Bay boaters, owning a cabin cruiser already feels like freedom.
February 18, 2026
You have probably read several boating magazine articles on how to winterize your outboard, diesel engine, fresh
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