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Guest Crew

We are looking forward to a busy sailing season in 2023 featuring more than a dozen guest crew experiences on the Chesapeake, Atlantic, and Gulf Coast. As guest crew experiences are scheduled, they are added to the schedule below.

Be advised that all guest crew will be required to read and adhere to Pride, Inc.’s COVID-19 policy.

Considering a Guest Crew Position?

Guest Crew at the HelmDo you have a passion for sailing or a love of adventure and the great outdoors? Sailing aboard Pride of Baltimore II might be your opportunity to experience the hands-on challenge of sailing a traditional ship. As guest crew, you will work alongside Pride‘s professional crew and participate in all aspects of life aboard the ship — up to your level of interest and ability. You will stand watch, steer the vessel, help with ship’s maintenance, and more.

Pride typically sails with a professional crew of 12 men and women, including the captain, ship’s cook, two mates, bosun, engineer, and six deckhands. There are three passenger cabins with two berths each available for guest crew, allowing up to six guest crew to share co-ed accommodations.

Grab your gear and come aboard Pride of Baltimore II for an overnight sailing adventure! Applications are reviewed on a first-come, first-served basis. Scroll down to view this year’s guest crew experiences (we add to the list as we confirm Pride‘s schedule, so check back periodically).

Below are some useful links about our guest crew opportunities aboard Pride:

What is it like to be guest crew? Check out these resources from folks who came aboard:

Guest CrewCancellation Policy: Guest crew reservations may be canceled up to ten business days or more prior to departure with a full refund. To cancel an existing reservation, please contact Pride of Baltimore, Inc. at 410.539.1151 or Cancellations made fewer than ten business days prior to a departure will not be refunded. Should the captain or Pride of Baltimore, Inc. cancel the guest crew experience due to weather or extenuating circumstances, a full refund will be given.


2023 Guest Crew Passages

If you are interested in sailing on one of the listed passages, apply by clicking the link in the schedule below for any experiences for which there are still spots available. If there isn’t an active link for a particular experience, that experience is not open for applications. We will notify you by email within seven business days of receipt of your application if you have been approved for a passage. Upon application approval, you will be asked to provide additional information and remit payment within three business days to Pride of Baltimore, Inc. Everyone must complete the application forms, regardless of past guest crew status.

Additional guest crew voyages are added as they are scheduled. 

PassageBoard DateDeboard DatePriceAvailability
Baltimore to St. Mary’s CityJune 20June 22 $375Apply Today
St. Mary’s City to Baltimore June 25June 27$375Apply Today
Baltimore to Gloucester

Sail up the coast from our home waters of the Chesapeake to the North Shore of Massachusetts and the historic town of Gloucester.

June 30July 6$900Apply Today
Gloucester to Baltimore

The perfect East Coast sailing adventure, sail down the coast from Gloucester to Baltimore.
July 9 July 15$900WAITLIST
Governor’s Cup Yacht Race

Celebrate the 50th anniversary of the oldest and longest-running overnight sailboat race on the Chesapeake Bay, which starts in Maryland’s current capital, Annapolis, and ends in Maryland’s first capital, St. Mary’s City.
August 3August 6$475WAITLIST
Great Chesapeake Bay Schooner Race

The GCBSR is one of the most iconic schooner races in the world. Race from Baltimore to Norfolk in company with dozens of schooners, while working alongside our professional crew, standing watch, pulling lines, taking the helm, and more.
October 5 October 7$1,000WAITLIST