Guest Crew

Sail Into the 2026 Season with Pride of Baltimore II

In summer 2026, Pride of Baltimore II will take part in the nationwide Sail250 commemoration, sailing along the Chesapeake Bay and Atlantic Coast as part of this historic milestone. These voyages offer a unique opportunity to sail as guest crew while participating in officially recognized events in ports along the route.

Below are the currently available passages for the season. Additional 2026 guest crew legs will be announced as plans are finalized.

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)

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.

2026 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
Baltimore to New York A bucket-list-worthy sail from Baltimore to New York City aboard Pride of Baltimore II, taking part in what is being hailed as “the greatest celebration in our nation’s history.” After sailing up the coast to New York, guests will have the opportunity to remain onboard for the Opening Parade of Sail on July 3 and celebrate our nation’s birthday by participating in the Sail4th 250 Parade of Tall Ships.	June 30	July 5	$1,800	Sail Sold Out — Join the Waitlist
New York to Boston The journey continues as you sail with Pride of Baltimore II from New York to the final major event of the Sail250 celebrations at SailBoston. Guests will have the opportunity to stay aboard the ship and participate in the Sail Boston Parade of Sail on Saturday, July 11, disembarking the following morning.	July 7	July 12	$1,500	Sail Sold Out — Join the Waitlist
Great Chesapeake Bay Schooner Race Join Pride of Baltimore II for one of the Chesapeake Bay’s most iconic sailing events, the Great Chesapeake Bay Schooner Race. Guest crew are welcomed aboard for pre-race festivities and the Parade of Sail before racing down the Bay against a fleet of schooners. Participants are also invited to attend the post-race awards and celebration. This is a race passage. Guest crew should expect a fast-paced, competitive environment.	October 14	October 17	$1,150	Sail Sold Out — Join the Waitlist
Boston, MA, to Portland, ME	July 19	July 23	$1350	Apply Today
Portland, ME, to Salem, MA	July 26	July 31	$1350	Apply Today
Salem, MA, to Lunenburg, NS	August 2	August 7	$1,650	Apply Today
Lunenburg, NS, to Boston, MA (US Passport Required)	August 10	August 15	$1,650	Apply Today
Boston, MA, to Rockland, ME	August 18	August 21	$750	Apply Today
Rockland, ME, to Greenport, NY	August 23	August 28	$1,000	Apply Today
Greenport, NY, to Havre de Grace, MD	August 30	September 4	$1,000	Apply Today
Baltimore to Cambridge, MD	September 27	September 30	$475	Apply Today
Check Back Later for Additional Guest Crew Passages