Family, First Dives, and Floating Ears

Hey Loopers — Chris and Deb here, back aboard SeaDAN and recording fresh from Founders Park Marina in Islamorada. We’re fresh off a whirlwind couple of weeks full of family, paddleboarding mishaps, and — big news — Chris is officially retired! 🎉

After wrapping up our final owner’s meeting in Louisville and enjoying the 4th of July with family (including future swimmer-in-chief, little Leon), we flew back into Fort Lauderdale, picked up a car, and returned to the Keys. But this time, we didn’t come alone.

We brought along Todd and Tammy — Chris’s brother and sister-in-law — for a week of Keys-style fun in the sun. And let us tell you, they didn’t just visit… they made memories.

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Dinghies, Sunsets, and Sea Critters

They arrived July 7th, and we wasted no time. First stop: Marker 88, our favorite sunset spot (and still the reigning tuna nacho champion). No snorkeling that night, but we made up for it the next day with a dinghy snorkel adventure. Highlights? Warm 89° water, clusters of lobster hiding in a concrete slab, and, of course, the now-legendary struggle of four adults trying to get back into a dinghy without injuring themselves. (We’re all fine. Mostly.)

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Wahoo, Mermaids, and Betsy the Lobster

We tried a new place — Wahoo’s Bar & Grill overlooking the Atlantic. Great food, great drinks, and an owner with great stories. Bonus? We were served by a self-proclaimed real-life mermaid. No complaints.

We also made another trip to Rain Barrel Village to visit Betsy, the giant lobster sculpture who now feels like an old friend. (Yes, we took more photos.)

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Key West: Putt Putt, Rum, and Tattoos

On Wednesday, we road-tripped down to Key West. On the way, we stopped at Porky’s Bayside Restaurant for cocktails and a sweaty, chaotic game of putt putt. (Spoiler: Todd won. Chris still claims everyone owes him money.)

In Key West, we parked near Papa’s Pilar Rum Distillery and Sloppy Joe’s, grabbed cigars, and strolled Duval Street. The ladies even got henna tattoos — palm trees and flowers that immediately smudged. Lesson learned: follow the instructions.

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Captain Tony’s, Hogs Breath & Sloppy Joes

Nightlife was a highlight. At Captain Tony’s Saloon, we were blown away by piano player Mike Brown, who had the whole bar clapping, laughing, and singing along. Over at Hog’s Breath Saloon, we caught Harley Ray, an incredibly talented singer-songwriter with Pearl Jam vibes and Kid Rock looks.

Sloppy Joe’s? Eh. The band was… there. Let’s just say we stayed for the experience, not the music.

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Paddleboard Wipeouts & Floating Ears

Thursday brought a hilarious return to paddleboarding. Todd bravely took the first post-happy-hour plunge (and surprisingly stayed upright). Chris… not so much. The second he stepped on the board, he faceplanted between two boats — losing his glasses, hat, and both hearing aids in one splash. A frantic mask-dive later, we found everything. Miraculously, it all still works.

Deb, of course, cruised calmly and even spotted a sea turtle.

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Steakhouse Surprise & Celebrations

We celebrated all the July birthdays (and Chris’s retirement) with dinner at Kindler — a fantastic new steakhouse tucked into Three Waters Resort. Incredible food, a friendly staff, and the most hilarious diving board belly flop from Todd earlier that day. If you haven’t been there: go.

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What’s Next?

We’re heading out soon to one of our favorite snorkel spots: Hens and Chickens Reef. Wind permitting, of course. Then we’ll hit a couple local breweries and filming locations from Bloodline, including Whistle Stop Pub & Grill, before Todd and Tammy head home to Springfield.

After that? It’s time to get serious about The Loop. We’ve got a solid weather window starting Monday and plan to push through Fort Lauderdale, hop into the Intracoastal, and start making some real wake.

We’re behind the other Loopers — most are in the Great Lakes or even Canada by now — but we’re not in a hurry. We’re Looping our way.

Thanks for following along. Don’t forget to subscribe so you get updates when a new episode drops. And if you’ve got paddleboarding tips, waterproof hearing aid suggestions, or just a favorite Tiki bar we haven’t tried — drop us a note.

See you on the water!