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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?

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 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 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.

PassageBoard DateDeboard DatePriceAvailability
Stay on the Bay 1

One night sail out of Baltimore. You will board Friday morning and sail all day. Spend the night on the ship and then be back in Baltimore Saturday morning with plenty of time to mow the lawn. Includes complimentary onsite parking.
April 5April 6$215WAITLIST
Stay on the Bay 2

A slightly longer experience. Spend two nights sailing with Pride II on the Northern Chesapeake Bay. Plan to board Friday morning and cast off lines spending two nights aboard. Plan to disembark Sunday morning in time to make it to brunch with the family. Includes complimentary onsite parking.

May 3May 5$430WAITLIST
Baltimore to Solomons

Sail down the bay from our home port of Baltimore to the town of Solomons.
May 7May 9$399Apply Today
Solomons to Havre de Grace

Sail from the town of Solomons, Maryland on the Patuxent River up the Bay to Havre de Grace on the mighty Susquehanna River
May 13May 16$525Apply Today
Deckhand for a Day

Participate in this hands-on single day sailing adventure from Baltimore to Annapolis. You can plan to board at 8 AM in Baltimore, debark in Annapolis by 4 PM where a van will take you back to Baltimore at approximately 5:30 PM. Included in this passage are a t-shirt and hat, complimentary lunch, free parking, and shuttle service back to Baltimore from Annapolis at the end of the sail.

May 31May 31$350WAITLIST
Annapolis to Bermuda Ocean Race

Join us for one of the longest offshore races on the East Coast. The challenging course combines inshore and offshore racing down the Chesapeake Bay, across the Gulfstream, and onto Bermuda. It enables sailors to fulfill a lifelong ambition of a blue water passage to an island known for its soft coral beaches. Ticket to Bermuda awards included.
June 6June 16$3,250
Bermuda to Baltimore

A bucket list-worthy adventure, sail from beautiful Bermuda blue waters across the Gulf Stream to our home waters of the Chesapeake Bay.
June 18June 28$1,575WAITLIST
Baltimore to Greenport, New York

Sail up the coast from Baltimore to the Village of Greenport, New York, situated on the eastern end of Long Island.
July 13July 18$950Apply Today
Greenport, New York, to Baltimore

Bring the ship back to the Chesapeake Bay and sail from Long Island down the coast to Baltimore.
July 21July 26$950Apply 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 2October 5$1,100WAITLIST
Norfolk to Annapolis

Sail up the Bay from Norfolk, Virginia, to Annapolis, Maryland.
October 6October 9 $529WAITLIST