Guest Crew

We are looking forward to a busy sailing season in 2025 featuring more than a dozen guest crew experiences on the Chesapeake Bay, East Coast, and Great Lakes. 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:

Sailing for the Next Horizon Aboard Pride of Baltimore II (Spinsheet Magazine, October 23, 2024)
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.

2025 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
Stay on the Bay (Baltimore to Baltimore) Includes Free Parking	April 25	April 27	$399	One Spot Open
Baltimore to Havre de Grace	April 30	May 2	$399	WAITLIST
Baltimore to Annapolis	May 7	May 8	$200	WAITLIST
Deckhand for a Day	May 12	May 12	$350	WAITLIST
Cambridge to Baltimore	May 18	May 20	$399	WAITLIST
Baltimore to Lunenburg	May 30	June 7	$1,500	Apply Today
Lunenburg to Clayton	June 8	June 19	$1,925	Apply Today
Clayton to Toronto	June 23	June 27	$825	Apply Today
Erie to Duluth	July 1/2	July 10	$1,500	Apply Today
Lake Superior Excursion (Duluth to Duluth)	July 13	July 16	$825	Apply Today
Duluth to Boyne City	July 20	July 25	$995	Apply Today
Boyne City to Sturgeon Bay	July 29	July 31	$500	Apply Today
Sturgeon Bay to Detroit	August 3	August 7	$825	Apply Today
Great Chesapeake Bay Schooner Race	October 15	October 18	$1,100	WAITLIST
Check Back Later for Additional 2025 Guest Crew Passages