Sailing Times

The Sea Gypsy sails up to six times daily from Annapolis Harbor beginning April 18, 2026. Pirate Adventures on the Chesapeake offers these family-friendly pirate cruises on the Chesapeake Bay, departing at the times listed below and returning approximately 1 hour and 15 minutes later.

Please plan to arrive 30 minutes before departure to allow time for face painting and dress-up before your child’s pirate adventure begins.

Advance reservations are strongly encouraged, as many Annapolis pirate cruises fill ahead of time — especially on weekends, holidays, and during summer months.

2026 Seasonal Sailing Schedule