My father and I decided to visit Key West and fish with the Jolly Roger II. Last time we did was April 2004, over 20 year years ago. Capt. Joe is one of the most experienced charter boat captains in Zoey West. Keep in mind that he specializes in trolling so you will be targeting most pelagic species. Both days were a tough bite but Capt. Joe and his first mate Brian worked their asses off and kept us on the fish. We limited out the first day on Mahi and caught a barracuda in addition. Second day was a bit tougher but we still cameout with a full cooler of Mahi. We will be coming back hopefully next April to target some different species.

Most guys take their wives to Paris or a fancy resort for their 20th wedding anniversary. You know — massages, room service, wine with weird names. Not me. I booked us a deep sea fishing trip with Captain Joe and First Mate Brian on the Jolly Roger II. Because nothing says “I love you, babe” like the smell of bait, fish guts, and sunscreen SPF 100.
And it turned out to be the best anniversary idea I’ve had in two decades. No joke.

The night before the trip, Captain Joe gave me the most honest pep talk ever: “I’m not God. I can’t make the fish bite or the weather behave.” Fair enough. I appreciated the warning — figured I’d probably be spending six hours on a boat, burning to a crisp while holding an empty fishing rod and trying to act like this was totally worth it.

Turns out… he was lying. Or at least being modest. Because the weather? Absolutely perfect. Blue skies, calm seas, warm breeze. No storm clouds, no squalls, not even a seagull that looked at me funny. The ocean practically rolled out the red carpet. And the fish? They wouldn’t leave us alone. We pulled in 19 Mahi Mahi and 4 barracuda like we were running some kind of underwater fast food drive-thru.

Captain Joe runs the show like a guy who’s seen everything — funny, laid back, and patient enough to deal with first-timers who have no idea which end of the rod is up (that would be me). His jokes were sharp, his advice was spot-on, and I only tangled the lines twice. Maybe three times. Brian probably untangled them before I noticed.

Speaking of Brian — the first mate might be part human, part fishing robot. The man never stops. He’s baiting hooks, setting lines, clearing decks, handing out tips, and telling ridiculous boat stories — all while acting like the circus going on behind him (me) is completely normal.

Even my wife — who originally thought this anniversary idea meant I’d forgotten a dinner reservation — was hauling in fish and grinning like a kid on Christmas. And she caught more than me, which she will remind me of for the next 20 years. Possibly longer.

By the time we got back to the dock, my arms were spaghetti, my face was sunburned in weird shapes, and I had the biggest grin I’ve worn since the wedding. Best day ever — and way cheaper than jewelry.

So if you want a fishing trip that feels like part comedy show, part National Geographic episode, and 100% worth it, book with Captain Joe and Brian on the Jolly Roger II. These guys are the real deal — and apparently, Captain Joe is God after all, because the fish sure listened to him.

Had an absolutely incredible day aboard the Jolly Roger II with Captain Joe and First Mate Brian! We filled the box with mahi, picked up a king mackerel and a barracuda, and the highlight of the trip was my daughter landing a 6.5-foot sailfish—an unforgettable moment and truly the catch of a lifetime.

Captain Joe and Brian were amazing from start to finish: knowledgeable, hardworking, and fun to be around. Couldn’t have asked for a better crew or a better day on the water. Highly recommend the Jolly Roger II for anyone looking for a top-notch fishing experience!

We had a great time with Captian Joe and First Mate Brian.  The wind made it a bit rough out there but the crew handled everything perfectly.  They still managed to get us fish.  We did a 8 hour trip targeting Sailfish.  Both Joe and Brian definitely did everything in thier Power to make sure we were catching.  Despite the weather.  Highly recommend.  We would love to do it again with this crew.

We went out on Dec 30.  Cold (60) and windy but the boat has a large enclosed area and Joe knows how to ride the waves and Brian , the first mate, knew how to catch fish.  We caught grouper, mackerel, yellowtail snapper.  Threw some back as we could only eat so much.  What we kept were great eating.  Totally do it again.  Actually thinking if coming back in may for mahi mahi fishing