Jolly Roger II 

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.

We had the BEST time with Jolly Roger Fishing Charter! From the moment we stepped on the boat, the crew was super friendly, fun, and incredibly helpful—especially for our group of 6 girls who were clueless haha. They made sure we were comfortable and helped us catch a ton of fish! They cleaned and filleted all the fish for us, and even recommended a local restaurant where we could bring our catch to have it cooked up fresh. It was such a cool experience from start to finish. Highly recommend!