I Love fish. I love fish fried, baked, grilled, even raw.

I love watching fish jumping next to boats and swimming in aquariums. But normally, I don’t love to fish, and there’s a reason why. I’m a terrible fisherman. As a child, I would fidget while my father tried to show me how to place bait on a hook. As an adult, the last time I tried to actually cast a line, I hooked myself. The most successful fishing trip I’ve ever taken was avoiding injury while dangling a line over the side of a sailboat on the Bay, settling back with a beer or three…and catching nothing. So the idea of this rod-and-reel novice trying to actually fish from a kayak seemed a bit, well, dangerous.

But when Capt. Chris Dollar pulled his trailer full of kayaks up to the boat launch at Janes Island State Park, he instantly put me at ease. A longtime guide and outfitter, Dollar specializes in kayak fishing, but he has been sharing his knowledge of the Chesapeake for many years. A former field educator for the Chesapeake Bay Foundation, he started his kayak guiding business, CD Outdoors, a few years ago and he’s never looked back.

“Every day is different, and that’s one of the challenges,” he says as he shows me some of his specialized gear. Dollar’s kayaks have special holes for fishing rods, boxes for tackle, and clips to keep you from losing your paddle in the heat of the moment when the fish bite. It’s not too much more complex than the average sit-on-top, but I’m fervently hoping that my lack of fishing talent won’t be one of his challenges.

Dollar also guides fly-fishing and light tackle trips up and down the Eastern Shore on his own larger boat, but he prefers the purer experience of kayak fishing. “A lot of folks like to get as close as they can to the water,” he explains as we lower two long green sea kayaks onto the floating dock. “In a kayak, there’s nothing there except for a piece of plastic. It’s you and the fish.”

As we launch our kayaks into the inlets surrounding Janes Island, I can see what he means. In the stable sea kayak, I have room to stretch out, and a comfortable seat, but my legs are hidden under a spray skirt in the bottom of the boat just beneath the waterline, my eyeline just below the top of the marsh grasses. I feel like a bobbling cork, ready to go where the current takes me, and at Janes Island, that could be any number of places.

The park is the perfect base for exploring the Chesapeake’s watery world. With 2,900 acres of marsh, beach, and highland, half of the area is only accessible by boat through a maze of waterways that lead out to the open bay. The park has created a 30-mile-long network of six paddle trails, complete with downloadable GPS waypoints to help plan trips. It would be easy to spend days here, and it’s even possible to spend the night on a camping platform out in the marsh, or in waterfront cabins on shore.

But it doesn’t take hours of paddling to sample the island’s beauty. Within five minutes of leaving the launch on Daugherty Creek, it feels like we’ve already left civilization behind. We’re the only ones paddling up the yellow trail, the only sounds the slap of water against the side of the kayaks, the soft plop of jumping fish, and the distant croaks of a startled heron. It would be easy to drift, just letting the current take the kayaks out toward open water, but Dollar has other ideas. These smaller inlets are great places to find hidden fish.

We paddle over to a quiet area of water near the edge of the marsh grasses, and another advantage of kayak fishing becomes clear—shallow water access—which starts to come in handy after trying my first cast. 

“Hold on, I’ll get it for you.” Dollar has to fish my first lure out of the weeds. At first, juggling the paddle and a rod (not to mention my nemesis, the sharp, barbed hook) is a little tricky. It takes a few minutes of patient instruction, but before long, I’m able to aim and cast smoothly, and enjoy being close to the creatures I’m attempting to catch—not only the Bay’s famous striped bass— but sea trout, croaker, crappie, or bluefish. But here the fish seem to be hard to find, so we decide to press farther on into the marsh.

We quickly settle into a quiet rhythm of paddling, pausing, and casting. Dollar has a sixth sense about when to jump in and help or explain something, and when to hang back and just let me float along and absorb our surroundings. “As a guide, you’re sort of like a bartender,” he explains. “You talk when you’re spoken to, and you know when not to open your mouth.”

After an hour paddling through the tall marsh grass, we emerge into a wide area of open water called Flatcap Basin, where five of the six water trails meet.

By now I can tell that Dollar really knows his fish. He points out areas where they like to hide or rest—under a nearby pier, in the quiet bends out through the marsh. Though I still haven’t caught anything, he’s achieving one of his other goals for his clients: an outdoor education.

“I try to do more than put fish in the boat,” he says “I’m helping people to understand more about why the fish are there at certain times of the year, what kind of tackle to use…It’s like problem solving.”

Unfortunately, however, I haven’t even come close to putting fish in my own boat. An unlucky cold snap the night before has driven them out into deeper water. I stop for one last cast, and then it happens. I become a fishing guide’s nightmare client—I drop my rod overboard. I lunge for it and miss and stare aghast as it sinks away toward the invisible bottom.

Despite all the new skills I’ve just learned, my fishing curse has struck again. Judging from Dollar’s patient reaction, I may not be the first client to make this kind of mistake.

For this trip, I guess that will be the one that got away.

CD Outdoors
Offers guided fishing trips on the Chesapeake and Atlantic coast as well as kayak rentals and sales. Fly- fishing and light tackle are available. Prices start at $150 for a half day, $400 for a full day of angling. 410-991-8468, http://www.cdollaroutdoors.com

Sara Edelson, a writer and television producer, lives in Washington, D.C.