Chesapeake Bay Cruising
Our Chesapeake Bay Cruising section features insights from liveaboards, tips and stories on cruising the Great Loop and Intracoastal Waterway (ICW), along with expert tips about boat maintenance and safety. For charter vacation stories visit our powerboat chartering section.
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.
July 28, 2025
You've heard of the Great Loop and probably even the DelMarVa loop, but have you ever heard of the Albemarle Loop?
July 14, 2025
When it’s hazy, hot, and humid, jumping on a boat and zipping across the water is a great way to cope. But let’s do it safely. Summer heat can creep up on boaters and take a toll.
June 25, 2025
“Who Moved My Cheese?” Many of you may remember the book with this title. The fundamental principle is that a mouse gets used to going through a maze and finding cheese at the destination.
May 22, 2025
A tongue-in-cheek reflection on de-winterizing your boat and preparing for the boating season.
May 21, 2025
In our last article, we discussed how to physically prepare for your voyage on America’s Great Lo
May 12, 2025
I have known boaters who have never dropped their anchor.
April 22, 2025
So, you’re looking for an adventure and have decided on America’s Great Loop.
March 31, 2025
Our Great Loop dream began when I saw in a doctor’s waiting room an article entitled “The Greatest Adventure You Have Never H