2026 Guest Crew Season Update
In 2026, Pride of Baltimore II offered nearly two dozen overnight guest crew experiences, sailing the Chesapeake Bay, racing down the Bay, and heading up the East Coast.
As of October 31, our 2026 guest crew sailing season has officially come to a close. Thank you to everyone who joined us aboard Pride II this year!
Looking Ahead to 2027 Passages
We are currently developing our 2027 sailing season. Guest crew applications are not being reviewed at this time. Please check back for updates as plans for next season take shape.
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:
- Guest Crew Approval Process
- Guest Crew Guidelines
- Tips and Things to Know
- Google 360 of Pride topside and below
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)
Guest Crew Refund Policy
- Cancellations 6 weeks (42 days) or more before your trip:
You’ll receive a full refund, minus a $50 cancellation fee per person. - Cancellations less than 6 weeks before your trip:
If we’re able to rebook your spot, you’ll receive a full refund, minus the $50 per person cancellation fee.
If we’re not able to rebook your spot, you’ll receive a credit toward a future passage.
If you choose not to accept a credit, your payment is non-refundable.
Guest Crew Schedule
Below is the schedule of available guest crew passages. Applications are reviewed only for actively scheduled passages with open spots. Applications not associated with an open passage will not be reviewed.
Apply using the active application link in the schedule below. Approved applicants will be notified by email within seven business days and must submit additional information and payment within three business days of approval. All applicants must complete the application forms, regardless of previous guest crew experience.
| Passage | Board Date | Deboard Date | Price | Availability | |
| Check Back Later for Additional Guest Crew Passages | |||||