Pirate Adventures on the Chesapeake has been creating unforgettable memories for families since 2002. Based in the heart of Annapolis, Maryland, we specialize in interactive pirate-themed cruises designed especially for kids ages 3–10.
Aboard our custom-built pirate ship, the Sea Gypsy, young buccaneers join the crew for a high-seas adventure complete with face painting, dress-up, treasure maps, and water cannon battles. Our mission is to spark imagination, encourage play, and provide a one-of-a-kind family outing that blends storytelling, adventure, and local scenery—including views of the U.S. Naval Academy and historic Annapolis Harbor.
Whether you’re planning a birthday celebration, a summer outing, or simply looking for fun on the water, Pirate Adventures offers a magical experience that’s equal parts entertainment and memory-making.