Guest Crew

We are looking forward to a busy sailing season in 2024 featuring more than a dozen guest crew experiences on the Chesapeake and East Coast. As guest crew experiences are scheduled, they are added to the schedule below.

Considering a Guest Crew Position?

Do 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:

Privateer for a Weekend (Chesapeake Bay Magazine, April 3, 2023)
The sail of my dreams on a tall ship (Green Bay Press-Gazette, March 3, 2017)
Sailing a tall ship across Superior (StarTribune, January 25, 2014)
Pride II Boston to NYC: Setting Sail on a Tallship (Video by Gale Browning, September 2013)

Cancellation Policy: Guest crew reservations may be canceled up to 30 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 pride2@pride2.org. Cancellations made fewer than 30 business days prior to a departure will be refunded less a processing fee. The processing fee will be $100. 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.

2024 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.

Passage	Board Date	Deboard Date	Price	Availability
Governor’s Cup Yacht Race Join us as race crew for the 51st annual Governor’s Cup hosted by St. Mary’s College of Maryland. The race is the oldest and most distinguished overnight competition on the Chesapeake Bay. This passage is a down and back sail. Approved guest crew will board in Baltimore the morning of the race, race down the bay to the St. Mary’s River, then return with the ship and disembark back in Baltimore early Sunday morning.	August 2	August 4	$475	WAITLIST
Baltimore to Plymouth Escape the summer heat of the Chesapeake Bay and sail up the coast from Baltimore to the coastal town of Plymouth, Massachusetts. There are no planned stops on this voyage.	August 8	August 15	$1,250	Apply Today
Plymouth to Baltimore Sail Pride II back home from Massachusetts Bay, down the East Coast to our home waters of the Chesapeake Bay. There no planned stops on this voyage.	August 18	August 25	$1,250	Apply Today
Baltimore to Cambridge Join us for a short overnight excursion down the Chesapeake to the Choptank River and historic Cambridge, Maryland.	August 28	August 30	$375	WAITLIST
Cambridge to Havre de Grace Sail from the shores of the Choptank River up the Bay to the headwaters of the Chesapeake Bay & the historic town of Havre de Grace.	September 2	September 5	$500	Apply Today
Baltimore to St. Mary’s City Join us for the sail to Maryland’s first European settlement and capital. This passage includes secure overnight parking and transportation back to Baltimore from St. Mary’s City.	September 23	September 26	$650	Apply Today
Great Chesapeake Bay Schooner Race The GCBSR is one of the most iconic schooner races in the country. They say it is two parties with a race in the middle. Join the ship in Baltimore then race down the bay to Norfolk working alongside our professional crew. Includes complimentary parade of sail ticket, prerace party entry, and awards party ticket.	October 2	October 5	$1,100	WAITLIST
Norfolk to Annapolis Sail up the Bay from Norfolk, Virginia, to Annapolis, Maryland.	October 6	October 9	$529	WAITLIST
Baltimore to Chestertown The final guest crew passage of our 2024 sailing season from Baltimore across the Bay to the colonial village of Chestertown on the beautiful Chester River. This passage includes secure overnight parking and transportation back to Baltimore from Chestertown	October 29	October 31	$550	Apply Today