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Photos by Charlie Levine

The sun had gone to bed hours ago in a sea of oranges and yellows spread across the sky. Constellations and planets winked at us as the Gulf of Mexico flattened out like a slick, black puddle. Classic rock tunes that I know every word to rang out of a head-high speaker. My best friend stood next to me, cracking jokes and talking smack. And every time my bait hit the bottom, it got bit.

Surely this must be what heaven feels like, especially after being stuck at home for weeks with dreams of adventure flooding my thoughts. But this was no dream. This was real-time, and I had just flipped another keeper over the rail.

Last fall, I decided I needed to do something special for my 45th birthday. I’d always wanted to fish the rich waters of the Dry Tortugas, a small group of islands about 70 miles west of Key West. The Tortugas don’t see much in the way of boat traffic, and the fishing, especially bottom fishing, is legendary. I figured 2020 was the year to make it happen, and I went about putting a trip together to celebrate my catapult into middle age. I knew of a boat in Key West that fished the Tortugas, but getting there would entail a 10-hour car ride and an overnight before departure, followed by a two- or three-day trip on the boat and the drive home. I didn’t have that kind of time.

At a fisheries meeting last November, I sat next to one of the captains who works at SeaTrek Fishing, an operation in Fort Myers Beach, Florida, that takes small groups of anglers south toward the Tortugas on multiday trips aboard a 65-foot headboat. He told me when to go, what to bring and what to expect. A few friends and I reserved our space for June 30 to July 2, paid an extra $10 a head to pick our bunks, and let the anticipation build over the next several months.

Mates Callum (left) and Robbie prepare the baits en route to the Dry Tortugas.

Mates Callum (left) and Robbie prepare the baits en route to the Dry Tortugas.

If you’re unfamiliar with the term “headboat,” it’s probably not what you’re picturing. Some folks also call them “party boats,” but that does not paint an accurate picture, either. Any partying on these boats entails cheap cans of beer, day-old sandwiches and a few seasick patrons chumming over the rail. The boats are usually beamy, aluminum jobs with plenty of room on the side decks for fishing. They chug, rather than cruise, and the captain’s plotter is chockablock full of coveted fishing spots.

I grew up fishing on headboats and have fond memories of running out to the codfish grounds aboard the Hel-Cat in the thick of a New England winter. The boat hailed from Groton, Connecticut, and it sported heated rails, with engine exhaust running through the hollow piping, to keep hands and gear from freezing and sticking to the cold metal. The vessel reeked of stale cigarette smoke, greasy egg sandwiches and cut squid. I know it sounds miserable, but I loved it. The camaraderie among fishermen. The different walks of life taking their spots on the rail. But most of all, the big cod that the boat put you on back in the day. That was the reward for waking early and fishing in nasty weather.

Headboats aren’t for everyone. They’re short on frills, but if you want to spend quality time with friends and family and carve out a memory or two (good and bad), headboats are a worthy platform. Fishing a headboat with a group of buddies is akin to sitting in a duck blind or camping off the grid. And in the case of this Tortugas trip, there’d be no cell signal, no news headlines, no interruptions. And that was a big part of the appeal. A chance to unplug, have some laughs and fill a cooler with fresh fillets.

Then came the pandemic. Life shut down. Charters were canceled. You know the story. The fishing trip was not my top priority, but I secretly hoped we could still pull it off, albeit safely. As Florida began reopening, the SeaTrek folks assured us they were taking extra precautions and that the boat would sail. I was incredibly grateful, as I needed the trip more than ever.

We met the boat at 8 a.m., paid our balance, had our temperatures checked and began the loading process. First tackle, then coolers, bags and personal belongings. We threw lines at 10 a.m., and after motoring past the entrance of the channel, the crew began the safety briefing. This headboat was cleaner than any I’d been on — new countertops in the galley, fresh paint on the bulkheads and a whiff of disinfectant in the air. We were told to wear masks in the cabin at all times and drink lots of water, and we were shown where to find life jackets.

I’d never seen the Gulf of Mexico so flat. The forecast called for zero to 2-foot seas and light winds, and it held true, thankfully. The top-heavy SeaTrek is known to bury the bow in big seas, sending coolers sliding to the stern and upchuckers to the rail. There was none of that on this voyage. After our briefing, my four friends and I found a shady spot to enjoy the 10-hour steam to the grounds. The captain had his sights set on some live bottom more than 100 miles offshore. Beers were cracked, as were jokes. Before long, my sides hurt from laughing, a feeling I hadn’t experienced in weeks.

As we chugged along, the deckhands — two 30-something guys named Robbie and Callum, who answered to Cole, Tallum or anything close to his South African name — filled the bait buckets with squid strips and other cut bait. They went through everyone’s tackle, tying on top shots of mono or advising a change in weight or hook size. Then they set a diving plug over the stern on a trolling outfit, as the boat traveled at 10 knots, an ideal speed for wahoo. Massive schools of flying fish skittered across the glassy surface. Dolphin played in the wake. The crew caught a nice kingfish on the plug and followed that with a 50-pound wahoo. I regretted not bringing a trolling rod.

We made it to our first fishing spot around dark. With only 18 anglers on the boat, there was ample space to put distance between ourselves, and the company rotates the prime spots on the stern so everyone gets time in the hot seat. The anchor went down, followed by the baits. After 15 minutes with no action, my buddies began to doubt the captain. “Well, you can always catch a buzz,” I said, digging a cold one out of the cooler.

Buddies Steve Wright and Rob Gatton are in the hot seat at the stern during a yellowtail snapper bite.

Buddies Steve Wright and Rob Gatton are in the hot seat at the stern during a yellowtail snapper bite.

The next stop — and the one after that, and the one after that — told a different story. Lines stayed tight, fish came up from the bottom, and photos were snapped. That first night, my friends and I had the stern. Rob and his 14-year-old son, Aiden, were constantly doubled up, laughing, sweating and hugging. Steve and I hooked one yellowtail snapper after another, and my other buddy Matt landed a trophy yellowtail, the biggest I’ve ever seen. At nearly 6 pounds, it’s what we Floridians call a “flag” because of the bright yellow stripes that extend down its flanks. They’re beautiful, fun to catch and great to eat.

We also got to know some of our neighbors on board. The mates kept referring to an older gent who never left his spot on the port side as “Uncle John.” I asked him about the name. “I’ve been fishing this boat for 30 years,” he said. “I’ve watched these guys grow up.”

Turns out John has an interesting back story. Now in his late 70s, he was a songwriter and musician in a doo-wop band in the early 1960s. He met Martin Luther King Jr. and told us tales of traveling through the segregated South with his mostly African-American bandmates.

Also aboard were a truck driver, a chiropractor and his brother, and a young serviceman out for a few laughs between deployments with his father and uncle, who sell roofing supplies. Everyone was friendly and happy to be on good fishing.

As the night wore on, my arms grew sore, my hands stunk and my cheeks hurt from smiling. When the mates told us it was time to rotate out of the stern, I asked what time it was. He glanced at his watch. “Take a guess,” he said.

I had no clue. “Midnight?”

“It’s 4:30 in the morning.”

I went inside to make a cup of coffee. I didn’t want to stop fishing.

The sun came up, and the mutton snapper began to bite. Nice fish, too. The relief captain, who’s also a rep for Accurate fishing reels, hooked into a whopper that weighed 20 pounds. The world-record mutton was caught in these same waters and didn’t weigh much more. We also found a large school of blackfin tuna, and the anglers in the bow blasted casting jigs at them. At some point, I began to ebb. Guys next to me were hooking up on the same bait I was using, but I couldn’t catch a cold. I didn’t care, so I decided to hit the rack for a couple of hours.

I couldn’t tell you what time it was when I was awoken by claims of grouper and red snapper, but I flew out of the berth and into the 100-degree heat. The fishing was still hot, and I hooked up on my second drop, but the barracudas and sharks had found us. My catch went bye-bye in a National Geographic-style explosion next to the boat.

Relief captain Austin Collins landed a whopper of a mutton snapper.

Relief captain Austin Collins landed a whopper of a mutton snapper.

We fished for another few hours, picking away at a bevy of species. I was in the same clothes I’d worn the morning we boarded the boat. My legs were covered in sweat, sunblock, fish scales and blood. My shirt was beyond ripe. Steve was fishing next to me, and I could tell he was fading. After a shark bit him off, he whispered that he was going to shower. The boat holds 1,000 gallons of water, so each person is allowed only one shower. You don’t want to waste that ticket, and Steve was first to break the seal. I kept fishing. When he returned from the cabin donning fresh clothes and smelling of Irish Spring, I asked how the shower was. “Absolutely perfect,” he said. “Good pressure and hot water.” I headed in.

The shower woke me up, took me out of my fish focus and made me human again. As I went out on deck in fresh duds with combed hair, the captain made the call to reel up the lines and get ready for the long steam home. I was happy with my decision as the guys jockeyed for the shower.

The sun went down, and we warmed up London broil, chicken wings and buttered noodles in the microwave. We ate on paper plates and used coolers as tables. The food was heavenly. The beers went down, the ball-busting resumed, and at 3 a.m. we were back at the dock.

I hadn’t felt that exhausted, yet recharged, in a long time. It’s amazing what a good fishing trip can do for the psyche.  

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