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 |
|---|---|---|---|---|
| May 25-27 | Baltimore to Solomons | Guest Crew Opportunity | Learn More and Apply to be Guest Crew | |
| May 27 Noon (time is tentative) | Fisherman’s Wharf, Solomons, Maryland | Arrival | The ship’s timing and route are subject to wind, weather, and other factors. You can track the vessel here: Pride II is Underway. Follow us on Facebook for updates from the ship. |
|
| May 30 1-3 PM | Fisherman’s Wharf, Solomons, Maryland | Day Sail | Adults $55 12 and Under $25 | |
| May 30 4-6 PM | Fisherman’s Wharf, Solomons, Maryland | Day Sail | Adults $55 12 and Under $25 | |
| May 31 Noon-2 PM | Fisherman’s Wharf, Solomons, Maryland | Day Sail | Adults $55 12 and Under $25 | |
| June 1 9 AM (time is tentative) | Fisherman’s Wharf, Solomons, Maryland | Departure | ||
| 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 6 5-8 PM | Broadway Pier, Fells Point, Baltimore | Pride of Baltimore Rum Release | $50 per | Step aboard the iconic Pride of Baltimore II for the launch of CASE 1 Rum: Spirit of Privateers, a bold limited-edition release created in honor of America’s 250th Anniversary. Crafted by Old Line Spirits and inspired by the daring legacy of Baltimore privateers, CASE 1 is a rich, 100-proof rum aged in ex-bourbon and ex-single malt casks, then finished with Amburana oak for a uniquely warm and adventurous character. |
| 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 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 19-23 | Boston to Portland | Guest Crew Opportunity | Learn More and Apply to be Guest Crew | |
| July 26-31 | Portland to Salem | Guest Crew Opportunity | Learn More and Apply to be Guest Crew | |
| July 31-August 2 | Salem, Massachusetts (tentative) | Salem 400 Events | Additional Information Coming Soon | |
| August 2-7 | Salem to Lunenburg | Guest Crew Opportunity | Learn More and Apply to be Guest Crew | |
| August 10-15 | Lunenburg to Boston | Guest Crew Opportunity | Learn More and Apply to be Guest Crew | |
| September 4-6 | Havre de Grace (tentative) | Port Visit | 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.