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2026 Sailing Schedule 

Follow Pride II as she sails near and far in the 2025-2026 season!

  • See the list below for the schedule of ports, deck tours, and public sails.
  • Want to sail with us overnight as guest crew? Check out our Guest Crew page.
  • To host an event, please see our Charters and Receptions page. The charter calendar is at the bottom of that page.
  • For updates from the ship and port arrival/departure times, follow us on Facebook. 
  • Pride spends a lot of time in the Chesapeake, providing grant-funded sails. To learn more about these opportunities, email Lori@pride2.org.

Date
Time

Location
(Click for Google Maps)

Event
(Click To Go to Event Page/Buy Tickets)

Price

Additional Information
November 3, 2025-April 15, 2026Baltimore, Maryland Winter Maintenance – Ship Closed to the Public
January 10
9 AM-4 PM		Winter Maintenance Berth, BaltimoreVolunteer DayWe’re hosting two volunteer days this winter. Space is limited, so advance registration is required. These hands-on days are a great way to spend time on the ship, connect with our crew, and contribute directly to her care.
February 7
9 AM-4 PM		Winter Maintenance Berth, BaltimoreVolunteer DayWe’re hosting two volunteer days this winter. Space is limited, so advance registration is required. These hands-on days are a great way to spend time on the ship, connect with our crew, and contribute directly to her care.
April 15Baltimore, Maryland End Winter Maintenance
April 30-May 3Alexandria, Virginia (tentative)Port Visit Additional Information Coming Soon
May 13Baltimore Museum of Industry, Baltimore, Maryland America’s Star-Spangled Ambassador: Legacy & Horizons Event Additional Information Coming Soon
May 15-17Baltimore, Maryland (tentative)In Port Additional Information Coming Soon
May 28-31Solomons, Maryland
(tentative)		Port Visit Additional Information Coming Soon
June 8-12Baltimore to RichmondGuest Crew OpportunityLearn More and Apply to b Guest Crew
June 11-15Richmond, Virginia Sail250 Virginia: Richmond SailfestAdditional Information Coming Soon
June 14-20Richmond to Norfolk Guest Crew OpportunityGuest Crew Opportunity
June 18-23Norfolk, VirginiaSail250 Virginia: NorfolkAdditional Information Coming Soon
June 21-25Norfolk to Baltimore Guest Crew OpportunityGuest Crew Opportunity
June 24-July 1Baltimore, Maryland Sail250 Maryland & Airshow BaltimoreAdditional Information Coming Soon
June 24Baltimore, Maryland Swimming with Pride in Baltimore Additional Information Coming Soon
June 30-July 5Baltimore to New York Guest Crew OpportunityGuest Crew Opportunity
July 4-8New York, New YorkSail4th250Additional Information Coming Soon
July 7-12New York to Boston Guest Crew OpportunityGuest Crew Opportunity
July 11-16Boston, Massachusetts Sail BostonAdditional Information Coming Soon
July 31-August 2Salem, Massachusetts (tentative)Salem 400 EventsAdditional Information Coming Soon
September 4-6Gloucester, Massachusetts
(tentative)		Gloucester Schooner FestivalAdditional Details to be Announced
September 11-12Baltimore, Maryland Defenders’ Day Weekend & Welcome Home Additional Information Coming Soon
September 26Baltimore, Maryland Sailabration: Sailing Traditions in InkAdditional Information Coming Soon
October 3Cambridge, Maryland Sailing the Choptank Through Ebony Eyes Additional Information Coming Soon
October 9-11Baltimore, Maryland Fells Point Fun Festival Additional Information Coming Soon
October 14-18Baltimore to NorfolkGreat Chesapeake Bay Schooner Race Additional Information Coming Soon
October 29-November 1Chestertown, Maryland Sultana Downrigging FestivalFestival Information
Check back — we may add additional events!



*Child pricing intended for those 12 and under. Parents/guardians are asked to bring USCG-approved personal flotation devices for children under seven.

NOTE: Dates, times, and locations for all deck tours, sails, and other events are subject to change. All events are weather-dependent.