“OK, what’s the first bet?” Craig asks, walking out of the bait shop with a rented rod and a bucket of live shrimp. “How about $30 on who catches the first fish?”
“Done,” I say, dropping my line into the inky green water before Craig can even get situated.
We’re standing on a pier at the northern end of the Sunshine Skyway Bridge, a 4-mile span across the mouth of Tampa Bay. Both ends have fishing piers, operated by the state (floridastateparks.org; 727-865- 0668), that run alongside a section of the main bridge, as well as a 24- hour bait shop. Soon after landing in Tampa, Craig and I pointed our rented Jeep toward the Skyway, paid the admission fee ($4 a car plus $4 per person) and rented rods for $10 each (cash only). Now we’re competing to see who’s the better angler.
A year ago, Craig moved to Cape Cod from the suburb of Boston where we’d both lived for more than 20 years — and he’s been boasting about his fishing prowess ever since. (In truth, we’re both beginners.) The weeks leading up to this trip have been filled with trash talk. “I’m heading to the gym — need to be able to reel in the giants I’ll be catching,” he’d texted me. Now, with hooks in the water, it’s time to put up or shut up.
Within 30 seconds of casting, Craig starts reeling. Cackling, he pulls in an 18-inch ladyfish, a slender white-bellied species that anglers consider a “trash fish.” He removes the hook and gives it a kiss. “That’s $30,” he says, throwing it back.
Many people consider Key West to be Florida’s premier fishing destination. But this region along Florida’s western coast — which includes the inshore areas of Tampa Bay and warm Gulf of Mexico waters along the beaches of St. Petersburg and Clearwater — is more conveniently located for many Sunshine State visitors, near Tampa International Airport. We’ve missed the season for tarpon, the acrobatic fish that routinely reach 50 pounds. But we have plenty of other species to target. Over a long weekend, we’ll fish three ways: off this popular fishing pier, with a group of strangers on a party boat, and on a private charter with an experienced guide. Beyond the fishing, Tampa offers a vibrant cultural scene with food trucks, outdoor concerts, and idyllic weather. But mostly, we aim to make good on that traditional fisherman’s boast: “I caught one this big.”
The next morning, we’re at Hubbard’s Marina in Madeira Beach to board the Friendly Fisherman, an 80-foot vessel that will carry us and 33 others on a five-hour offshore excursion (hubbardsmarina.com; 727-393-1947). We pay $75 per person plus $7.50 each for rental rods, $12.50 each for a lunch package, and $10 for fancier bait. (Pro tip: skip the lunch, which requires waiting in line, as well as the bait upgrade; the cheaper bait stays on the hook better.) We spend the next 70 minutes motoring to a spot roughly 9 miles off the coast while crew members Dennis and Skraps teach us how to bait our hooks with chopped squid and send the weighted line to the bottom. Finally, the engine quiets and the captain’s voice comes over the PA system: “Fire ‘em down!”
We follow his instructions and begin waiting. Suddenly Craig begins reeling: On his first cast, he’s again caught the first fish — a grunt (a whitefish with good “food value”) — earning another $30. Skraps comes over to unhook it. “It’s a keeper,” he declares, sticking a numbered string through its gill before putting it on ice.
Over the next few hours, I land a hogfish, some red groupers, and assorted bait fish — nothing large enough to keep. I pull up a puffer fish, a poisonous breed that inflates its throat like a balloon as a defensive measure — the day’s most unusual catch. Around us, more experienced anglers are filling the ice chest. Discouraged, I wave over the captain. “What am I doing wrong?” He explains that the day’s conditions are challenging: The rough water is churning up mud from the bottom, obscuring the fishes’ ability to see our bait. He grabs my rod, casts to the bottom, and within five seconds begins reeling. He pulls up a small grouper — a reddish game fish that’s out of season and has to be thrown back. “It’s all in the feel,” he says. “It’s this very gentle tap-tap-tap. When you feel that, start reeling as fast as you can.”
As the trip winds down, I’ve caught more fish than Craig, but his keeper was the first and biggest; I have zero keepers, and I’m down $60. The captain announces that we have five minutes left to fish. I send my bait to the bottom one last time. Tap-tap-tap. I reel furiously, pulling up a grunt. Skraps measures it. “It’s a keeper!” he yells — the fishing equivalent of a buzzer beater.
Back at the dock, Dennis and Skraps fillet our two fish and hand us a plastic bag with some dinky morsels of white flesh. “Maybe enough for a fish taco,” Dennis says. Craig takes a photo of the two-dozen fish held by the couple behind us and texts it to friends back home, claiming they’re ours. “Today’s catch,” he lies. “Big time dinner tonight!”
For lunch, we grab a table next door at the Friendly Fisherman (gofriendlyfisherman.com; 727-391-6025), which offers a “hook and cook” service for those who fish with Hubbard’s Marina: For a modest fee, the cooks will broil, blacken, or fry whatever you catch. We hand the waitress our bag. “There’s not much here, so I don’t have to charge you,” she says cheerily, returning with an appetizer-sized plate. “I’ve seen smaller,” she says. Doused in lemon and tartar sauce, it tastes . . . about the same as fried fish you’d get anywhere. Plump raw oysters, cocktail shrimp, and steamed mussels make for a substantial (and surprisingly inexpensive) meal.
For lodging, we’ve chosen the Aloft Tampa Downtown (marriott.com; 813-898-8000; from $154), a Marriott hotel, which, for our purposes, is a mixed bag. Our room is spacious and clean; the pool overlooks Tampa’s bustling Riverwalk; we have great restaurants within walking dis- tance. The downside is that we’re 24 miles from St. Petersburg, where most of the fishing takes place. We’d realized that when we booked it, but hadn’t accounted for the heavy traffic — or how tired we’d be after long days on the water. Next time, we’ll stay closer to the Gulf to reduce the driving, perhaps at the less pricey Fairfield Inn & Suites in St. Petersburg, also run by Marriott (727-685-1555; from $118).
Two miles up the Riverwalk from our hotel is Ulele (ulele.com; 813-999-4952), where we ate lunch on our first day in town. The restaurant, which focuses on Indigenous-inspired food, features an expansive dining room with a view of the river. We tried the fried alligator appetizer; chili made with alligator, boar, duck, and venison; pan-seared pompano; blackened redfish; and Key lime pie. Afterward, we understood why Ulele shows up on lists of the region’s best restaurants. Ybor City, Tampa’s historic district where old-timers still hand-roll cigars in storefront windows, is worth checking out. The Columbia Restaurant there (columbiarestaurant.com/ybor-city-tampa; 813-248-4961), Florida’s oldest restaurant, features energetic flamenco dinner shows. Although locals view Columbia as a tourist spot, inside it feels authentically old, and the food — empanadas, garlic shrimp, ribeye, and a breaded chicken dish with a citrus sauce, called Pollo Manchego — is first-rate. Ybor City also offers Tampa’s most concentrated neighborhood of bars and nightlife. Things pick up around 11 p.m., people say, but that’s perhaps not the best option for anglers looking to get on the water early.
On our third day of fishing, we meet Captain Chris Haught at a dock inside Maximo Park in St. Petersburg. I’d chosen Haught’s Inshore Charters service (inshorecharters.com; 727-420-4429) based on his quarter-century of local experience and his “no fish, no pay, no excuse” guarantee. Haught charges $400 for a four-hour fishing trip, less than some competitors. Before meeting us, he’d spent 90 minutes in his open 22-foot boat using a net to catch small baitfish, which we’d use on our hooks on this day.
Once Craig and I get aboard, we come up with a game plan: We’ll make the 20-minute ride to fish off the Gulf beaches of St. Pete. Then, depending on conditions, we’ll seek smaller species in the shallower waters inside Tampa Bay.
When we arrive off the beaches, Haught is disappointed. The water is murky. There are few boats or birds nearby; if the fish were biting, he’d expect more of both. After 10 minutes of circling, we start to head back into Tampa Bay. Suddenly, birds descend on a nearby spot. We put our lines in the water. Within seconds, my rod jerks and my reel screams as a fish begins tearing out line. The tip of my rod bends sharply, and I follow Haught’s instructions to let the fish run, allowing it to tire before opportunistically reeling in line. The fight lasts five minutes before I pull in an 8-pound bonito — a greenish rainbow-backed fish that’s heavier than it looks. Haughty takes out the hook, grabs a photo, and returns the fish to the water. (We opt not to keep any fish on this day.) I cast again and quickly catch a second bonito.
At the front of the boat, Craig is unusually quiet. By now, we’ve added wagers for the day’s biggest fish as well as the most total catches. After an extended dry spell, he begins catching a string of lizardfish, a brownish, cylindrical, toothy breed. “You’re the lizard whisperer,” Haught says. We each pull in a couple of Spanish mackerel — long and thin with sharp teeth.
We move to the bay and begin landing a variety of fish: sea trout, catfish, and ladyfish, which jump and fight when hooked. Halfway through the trip, my bonito is not only the first caught but also the biggest, so Craig focuses on his fish count. “It’s 12 to 9,” he says, with him leading. We hit a thick school of ladyfish, and I begin reeling in one after another. Haught points to me. “This guy’s the silent assassin over here,” he says. By the end of the day, we’ve caught about two dozen fish apiece, and apart from times when we were changing locations, we couldn’t recall going 10 minutes without one of us catching something. That’s partly because Haught managed the operation so efficiently — keeping us on top of fish, quickly baiting our hooks, and effortlessly removing the fish we caught.
We’d paid for a four-hour trip, but nobody watches the clock. With ‘70s rock blaring and Bud Light on ice for Craig and me, this feels more like three friends hanging out, not a guide and clients. After five hours, Haught says we should head back to the dock — but, on the way, we stop for 15 minutes to watch a school of manatees. (Haught says he added extra time, free of charge, because the fishing by the beaches had started out more slowly than he’d hoped.)
Spending hours in a small, open boat isn’t for everyone. There’s no shade and no bathroom. Although neither Craig nor I suffer sea sickness, we feel slightly dizzy hours after disembarking. Later that night, my ankles ache, a reminder of the effort it takes to stay upright on a bobbing surface. The next morning, before catching our return flights, we reflect back on our three fishing experiences. The Sunshine Skyway Pier was cheap, convenient, and a reasonable choice for people who get seasick or wouldn’t want to be stuck on a boat for hours.
The day’s poor fishing conditions made it hard to fairly judge the party boat. But the transit time to the offshore fishing spot felt too long, and the fish we caught didn’t fight like the ones we’d caught on the charter, limiting the excitement.
Although not everyone can afford a private charter, it was the hands-down winner — a more customized outing with concierge-level service. The fish we caught put up a fight that created more of a challenge. If we come to Tampa again, we’ll come earlier in the year and hire Haught to take us tarpon fishing.
We don’t return home with any stuffed trophies. But, thanks to my luck on our final day of fishing, I head home with $30 of Craig’s money — and bragging rights that are priceless.
Daniel McGinn is an executive editor of Harvard Business Review. Send comments to firstname.lastname@example.org.