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.

January 16, 2020
Cruising in Newfoundland is distinctly different than cruising in other regions.
January 15, 2020
How many stories end with a madly in love couple sailing off into the sunset together? It’s a classic trope for a reason.
January 6, 2020
Navigating the Intracoastal Waterway's (ICW) shallow and constricted waters can seem daunting.
January 6, 2020
Do you think you can motivate yourself to hit 100 days on the water in 2020? Many of our readers listed this as a goal for the New Year.
December 12, 2019
Among the many benefits of owning a cruising 
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.