Come aboard the Calico Jack Headboat!Enjoy a day of family fun, relaxation, bay fishing, or sightseeing in the Assawoman Bay of Ocean City, Maryland. The Calico Jack is a 32 passenger Coast Guard inspected Chesapeake Custom Headboat; offering daily fishing trips, private charters, private parties, and private sunset cruises. The Calico Jack Headboat offers 2.5 hour bay fishing trips. No fishing license is required and we fish for flounder, rockfish, sea bass, tautog, trout, and croaker. The Captain/owner is local to Ocean City, MD and will take you to some of the best bay fishing spots that Ocean City has to offer. The boat is designed to offer you the most comfortable experience with bench seating, restroom, and radio. The Calico Jack departs from 32nd street bayside, next to Jolly Roger Amusement Park. The Calico Jack heaboat is fun for all ages! The best bay fishing in Ocean City MD!