Chesapeake Bay Cruising

Our Chesapeake Bay Cruising section features insights from liveaboards, charter vacation stories, tips and stories on cruising the Great Loop and Intracoastal Waterway (ICW), along with expert tips about boat maintenance and safety.

December 11, 2019
Last year my younger brother Tyler, a registered 50-ton master captain, sold his beloved deadrise workboat for a Henriques 35 Maine Coaster, with dreams of heading offshore.
November 18, 2019
As in houses, organized boats look a whole lot prettier. Here are my recommended 12 steps for boat organization.
November 7, 2019
Ryan and Tera Gubernat are no strangers to chartering or the boating lifestyle. Hailing from the Chesapeake, they just recently returned from a BVI charter.
November 6, 2019
There is more to being a captain than boat handling skills. After five years on the water I have identified these following attributes for a good captain.
October 30, 2019
Pooles Island, near the mouth of the Gunpowder River, is a small island that has been untouched by
October 28, 2019
The Great Loop is a 6000-mile circumnavigation of the eastern portion of North America, primarily comprised of protected waterways.
October 21, 2019
I continue my love-hate relationship with our boat. I still hate worrying about how the errands are going to get done, but I love a nice day on the Bay.
October 14, 2019
Here are some key winterization tips to prepare your boat before the first freeze. Often times, winter is closer than you think.
October 14, 2019
You can’t mention selling your boat without several people nodding sagely and tossing out the old aphorism about the two happiest days of boat ownership: the day you
October 7, 2019
This boat is a blast! Bruce Ogden and I ran around the West River powered by a 90-hp outboard at up to 40 mph at wide open throttle.
October 2, 2019
Cruisers from the Northeastern Seaboard and Canada will head to Hampton, VA, October 17-20 for the annual H
September 27, 2019
I have many fond memories as a child exploring far-away destinations from Lake Winnipesaukee, NH, to Islamorada in the
September 16, 2019
As we welcome the beautiful weather of fall, we are also reminded of Hurricane Isabel, which hit the Chesapeake region in September of 2003.
September 13, 2019
If your yacht club isn’t going to Croatia this year or your boat won’t make it to the Grenadines in a week, don’t worry, you can still enjoy an exotic boating vacation by chartering.
September 9, 2019
Personable Annapolis and Kent Island resident Phil Besche sat down with PropTalk recently to talk all things waterskiing.
August 19, 2019
As most of us were preparing for the cold dark days of winter last November, Annapolitans Sandy Nuwar and Jeannie Hillock were snorkeling with their friends and families in the clear blue waters of
August 2, 2019
One night last fall on a boat delivery south to Norfolk from Rhode Island, the mate noticed that there didn’t seem to be any red and green reflections from the running lights up on the bow, just af
July 19, 2019
With boating season in full swing many of us will enjoy opportunities to welcome friends and family on our own boats, and we’ll also get the pleasure of being