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 30, 2023
Upon selling Walden, a 1987 Ericson 38-200 sailing sloop, and moving from South Florida to Annapolis, MD, it was time for a new
November 29, 2023
This fall, a group of 45 international cruisers teamed up with a group of Annapolis-based cruisers, both power and sail, to experience the beauty of the
November 16, 2023
As the cold weather sinks in, we wanted to share some cold water safety tips for boaters on the Chesapeake Bay
November 13, 2023
Perhaps the most difficult task for a boat owner is attempting to make paint adhere to metals that are subject to the ad
November 8, 2023
It’s once again time to (regrettably) put the boat away for the winter and complete the necessary winterization procedures.
November 3, 2023
Croatia is a strange place. It’s part Eastern Europe and part laidback Mediterranean.
October 21, 2023
Jimmy Buffett passed away on the Friday of Labor Day Weekend.
October 17, 2023
The first day of charter is usually hectic.
October 11, 2023
The Atlantic Intracoastal Waterway (AIWW, or for our purposes just the Atlantic ICW) and the Gulf Coast Intracoastal Wa
October 4, 2023
Finding the proper boat for one’s boating needs is paramount in determining whether boating will be a blissful and blithe
September 18, 2023
TrawlerFest Baltimore is THE show for cruising enthusiasts, with a wide selection of seminars and also an in-water boat show and social activities.
August 30, 2023
The Sea of Abaco forms the northernmost boundary of the Bahamas, and it’s a compact yachtie playground, perfect for a weeklong
August 25, 2023
The second event of the summer for the Southern Maryland Boat Club was held at the end of July and feature
August 24, 2023
When you live near and cruise the Chesapeake Bay, it is hard to imagine better cruising grounds. In fact, the Bay is a draw for cruisers around the world.
July 25, 2023
Now, you might be asking, what is an article about Wisconsin doing in a Chesapeake Bay publication?
July 24, 2023
In May, my son-in-law, with help from my grandsons, completed our second year participating in the Maryland
July 7, 2023
As I write this (late May) I am sitting on the boat in Norfolk’s Waterside Marina, waiting out weather to make my final 140 mile push up the Bay to Annapolis.
July 7, 2023
It's critical to practice safe boating practices this summer.