The Chesapeake Bay is an excellent striper fishery, and I am very fortunate to live relatively close to it. For years, my friends and I headed to the Eastern Shore to fish with Brian Councell (www.councellcharters.com). I've fished with Brian many times and each time he has delivered quality fish.
My biggest fish so far with Brian was a 43.5-inch, 40-pound female striper caught during the catch and release season of 2009. I’ve caught at least one other trophy (40-inch) striper and many other stripers in the 36 to 40 inch range, as well as lots of smaller stripers, some bluefish, and some cownose rays. Brian is a tournament winner himself and one of the hardest-working captains with whom I have ever fished. He is without a doubt the man to fish with for Chesapeake Bay striped bass.
Update June 2021: Despite living less than three hours from the ocean, I do not saltwater fish. In fact, the last time was when I finished my 50 state quest in Hawaii in May 2015. But, as a Father's Day 2021 treat to myself, I went shark fishing for the second time in my life. I chose Chasin' Tides out of Ocean City, an outfit that catches trophy sharks regularly, and I was not disappointed. My first shark of the day was a trophy, an 8.5-foot, 250-pound sand tiger shark. He took quite a few runs and continued to go crazy even after the mate had tail-roped him. I managed another, smaller shark before the end of our short morning trip. It was a fun experience and I look forward to going back.