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.

September 7, 2021
A few years ago, not long after Hurricanes Irma and Maria tore through the Caribbean, I took my first bareboat powercat charter in the
September 2, 2021
The Chesapeake Bertram Rendezvous returns on September 18 at Higgins Yacht Yard in St.
August 27, 2021
Last month we reported on the planning and communicating complexity associated with a large group cruise from the Bay
August 20, 2021
UPDATE: This event has been canceled. Mark your calendars for Deale Dinghy Day, August 28 on Rockhold Creek i
July 28, 2021
Come See Vintage Race Boats from the 1950s, ’60s, and ’70s… and Talk to the Drivers!
July 26, 2021
It is likely that many of you have been on some sort of a group cruise.
July 26, 2021
Welcome to part four of how to go cruising on a trailerable powerboat and do it with maximum flexibil
July 6, 2021
This is the third installment of how to go cruising on a trailerable powerboat (and do it with limite
July 1, 2021
With more new boaters on the water than possibly ever before, that “secret” raftup spot or anchorage of yours mig
June 22, 2021
Exposure to moisture is an undeniable aspect of boat ownership.
June 22, 2021
The U.S. Coast Guard Auxiliary is an organization of volunteers that serve our nation and local communities in 835 local units.
June 22, 2021
The Upper Chesapeake Ski Club (UCSC) is a family-oriented water ski group located in Elkton, MD.
June 3, 2021
Mark your calendars for the annual Southern Maryland Boat Club Summer Regatta scheduled for July 30 to
June 1, 2021
If you are one of the boaters who attended the recent Bay Bridge Boat Show with the goal of buying your very first boat or upgrading to your next boat, you definitely need to read further.
May 28, 2021
This series is about one woman's solution for cruising: buying a trailerable boat. This installment covers the boat, motor, and tow vehicle.
May 23, 2021
Annapolis boatbuilder and self-proclaimed “mad scientist,” Tony Smith, woke up to an unusual sight
May 23, 2021
The Classic Yacht Club (CYCA) of America kicked off the 2021 season with an extra special event, because 2021 marks the 50th anniversary of CYCA. 
May 14, 2021
It’s that time of year again—time to send in your submissions for our Dog Days of Summer August Cover Contest.