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 | Location | Event | Price | Additional Information |
|---|---|---|---|---|
| November 3, 2025-April 15, 2026 | Baltimore, Maryland | Winter Maintenance – Ship Closed to the Public | ||
| January 10 9 AM-4 PM | Winter Maintenance Berth, Baltimore | Volunteer Day | We’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, Baltimore | Volunteer Day | We’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 15 | Baltimore, Maryland | End Winter Maintenance | ||
| April 30-May 3 | Alexandria, Virginia | Port Visit | Additional Information Coming Soon | |
| May 8 6-8 PM | Port Covington Marina, Baltimore Peninsula | Day Sail | Adults $55 12 and Under $25 | |
| May 9 3-5 PM | Port Covington Marina, Baltimore Peninsula | Day Sail | Adults $55 12 and Under $25 | |
| May 9 6-8 PM | Port Covington Marina, Baltimore Peninsula | Day Sail | Adults $55 12 and Under $25 | |
| May 14 | Constellation Pier 1, Baltimore, Maryland | Legacy and Horizons: A Rededication of Pride of Baltimore II | Attend or Sponsor – Learn More Here! | |
| May 15-17 | Baltimore, Maryland (tentative) | In Port | Additional Information Coming Soon | |
| May 21 6-8 PM | Constellation Pier 1, Baltimore, Maryland | Day Sail | Adults $27.50 12 and Under $12.50 | |
| May 22 Noon-5 PM | Constellation Pier 1, Baltimore, Maryland | Deck Tours | Free | Climb aboard for a tour of the ship! Meet our crew and learn the history of privateers and Baltimore clippers. |
| May 22 6-8 PM | Constellation Pier 1, Baltimore, Maryland | Day Sail | Adults $55 12 and Under $25 | |
| May 24 10 AM-6 PM | Constellation Pier 1, Baltimore, Maryland | Deck Tours | Free | Climb aboard for a tour of the ship! Meet our crew and learn the history of privateers and Baltimore clippers. |
| May 25 10 AM-6 PM | Constellation Pier 1, Baltimore, Maryland | Deck Tours | Free | Climb aboard for a tour of the ship! Meet our crew and learn the history of privateers and Baltimore clippers. |
| May 25-27 | Baltimore to Solomons | Guest Crew Opportunity | Learn More and Apply to be Guest Crew | |
| May 27-31 | Solomons, Maryland | Port Visit | Additional Information Coming Soon | |
| May 31-June 2 | Solomons to Annapolis | Guest Crew Opportunity | Learn More and Apply to be Guest Crew | |
| June 3-4 | Annapolis overnight excursion | Guest Crew Opportunity | Learn More and Apply to be Guest Crew | |
| June 8-12 | Baltimore to Richmond | Guest Crew Opportunity | Learn More and Apply to be Guest Crew | |
| June 11-15 | Richmond, Virginia | Sail250 Virginia: Richmond Sailfest | Additional Information Coming Soon | |
| June 14-20 | Richmond to Norfolk | Guest Crew Opportunity | Guest Crew Opportunity | |
| June 18-23 | Norfolk, Virginia | Sail250 Virginia: Norfolk | Additional Information Coming Soon | |
| June 21-25 | Norfolk to Baltimore | Guest Crew Opportunity | Learn More and Apply to be Guest Crew | |
| June 24-July 1 | Baltimore, Maryland | Sail250 Maryland & Airshow Baltimore | Additional Information Coming Soon | |
| June 24 | Baltimore, Maryland | Swimming with Pride in Baltimore | Additional Information Coming Soon | |
| June 30-July 5 | Baltimore to New York | Guest Crew Opportunity | ||
| July 4-8 | New York, New York | Sail4th250 | Additional Information Coming Soon | |
| July 7-12 | New York to Boston | Guest Crew Opportunity | Learn More and Apply to be Guest Crew | |
| July 11-16 | Boston, Massachusetts | Sail Boston | Additional Information Coming Soon | |
| July 31-August 2 | Salem, Massachusetts (tentative) | Salem 400 Events | Additional Information Coming Soon | |
| September 4-6 | Gloucester, Massachusetts (tentative) | Gloucester Schooner Festival | Additional Details to be Announced | |
| September 11-12 | Baltimore, Maryland | Defenders’ Day Weekend & Welcome Home | Additional Information Coming Soon | |
| September 26 | Baltimore, Maryland | Sailabration: Sailing Traditions in Ink | Additional Information Coming Soon | |
| October 3 | Cambridge, Maryland | Sailing the Choptank Through Ebony Eyes | Additional Information Coming Soon | |
| October 9-11 | Baltimore, Maryland | Fells Point Fun Festival | Additional Information Coming Soon | |
| October 14-18 | Baltimore to Norfolk | Great Chesapeake Bay Schooner Race | Additional Information Coming Soon | |
| October 29-November 1 | Chestertown, Maryland | Sultana Downrigging Festival | Festival Information |
*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.