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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
June 24-June 30Baltimore, Maryland Sail250 Maryland & Airshow BaltimoreCome aboard!
June 30-July 5Baltimore to New York Guest Crew Opportunity
July 4-8New York, New YorkSail4th250Come aboard!
July 7-12New York to Boston Guest Crew OpportunityLearn More and Apply to be Guest Crew
July 11-16Boston, Massachusetts Sail BostonAdditional Information Coming Soon
July 19-23Boston to Portland Guest Crew OpportunityLearn More and Apply to be Guest Crew
July 23-27Portland, Maine Port of Call Visit details coming soon
July 26-31Portland to Salem Guest Crew OpportunityLearn More and Apply to be Guest Crew
July 31-August 2Salem, MassachusettsSalem 400 EventsAdditional Information Coming Soon
August 2-7Salem to Lunenburg Guest Crew OpportunityLearn More and Apply to be Guest Crew
August 7-11Lunenburg, Nova ScotiaPort of CallNo Public Events
August 10-15Lunenburg to Boston Guest Crew OpportunityLearn More and Apply to be Guest Crew
August 15-19Boston, MassachusettsPort of Call Additional Information Coming Soon
August 21-24Rockland, Maine Port of Call Additional Information Coming Soon
August 28-31Greenport, New YorkPort of Call Additional Information Coming Soon
September 4-6Havre de GracePort of Call Additional Information Coming Soon
September 11-12Baltimore, Maryland Defenders’ Day Weekend & Welcome Home Additional Information Coming Soon
September 26Baltimore, Maryland Sailabration: Sailing Traditions in InkAdditional Information Coming Soon
September 30-October 5Cambridge, Maryland Port of Call & Special Event: 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 22-26Fisherman’s Wharf, Solomons, MarylandPort of Call 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.