You know those people who say, “Someday I’ll write a book,” but then “someday” turns into a decade of re-watching The Office and scrolling TikTok? Yeah, we’ve all been there. But then there are people like Chris Harvey.
I recently had the absolute pleasure of chatting with Chris for the Fun in Key West podcast, and let me tell you, his energy is infectious. He’s our January author for the Book of the Month Club, and his debut novel, Son of a Son of a Pirate, is basically everything we love about Key West wrapped into paperback form. We’re talking pirates, hidden treasure, Jimmy Buffett references, and enough island vibes to make you book a flight immediately.
If you missed the episode, don’t panic. I’ve got the full scoop right here (plus some juicy details about where to find the best lavender cheesecake on the island). So, grab a margarita—or a cafecito if it’s before noon—and let’s dive into the mind of the man who turned a “someday” dream into a swashbuckling reality.
From Tech Exec to Parrothead Author
So, who is Chris Harvey? If you look at his resume, you’ll see a polished marketing executive who spent years grinding in the high-tech industry. But if you look at his soul? He’s a Massachusetts-born Parrothead who’s been following Jimmy Buffett since the 80s.
About 18 years ago, Chris traded the cold for the sunshine and moved to Florida, settling not far from Fort Lauderdale. He eventually “retired” from the corporate world to start his own business (which, let’s be honest, usually means working harder than before). But amidst the chaos of entrepreneurship, a thought popped into his head about two years ago.
He channeled his inner Jimmy Buffett—specifically the lyric “Someday I Will”—and decided to stop talking about writing a book and actually do it. He figured since he had zero free time, it was the perfect time to start a novel. Makes sense, right?
A Literal Son of a Son of a Sailor
Here’s where things get cool. Chris isn’t just writing about the sea because it’s trendy; it is quite literally in his DNA. When we started digging into his family history, the connections were wild.
His paternal grandfather was a Merchant Marine from Scotland who shipped war materials during WWII (and met Chris’s grandmother in Maine—classic romance). Go back a little further, and his great-grandfather was sailing masted ships from Maine to Cuba. Chris told me this ancestor worked his way up to first mate and was apparently quite the ladies’ man, racking up four marriages in his lifetime. (We love a messy historical tea spill).
But the kicker? Chris traced his genealogy all the way back to 1620. He’s a descendant of Stephen Hopkins, who stepped off the Mayflower. So, while Chris admits he’s not much of a sailor himself—he prefers terra firma—that respect for the ocean is baked into his bloodline. He proves that you don’t need to know how to tie a sheepshank knot to write a compelling sea adventure. You just need a good imagination and maybe a little ancestral help.
The Soundtrack of the Story
You can’t write a book called Son of a Son of a Pirate without paying homage to the Mayor of Margaritaville himself. The influence of Jimmy Buffett on this book is huge.
Chris confessed to hiding about 13 different Buffett lyrics throughout the pages. It’s like an Easter egg hunt for Parrotheads. If you know the songs, you’ll catch a phrase and immediately start humming A Pirate Looks at Forty.
The main character, Teach Taylor, is basically the ultimate Buffett fanboy. He runs a tour in Key West that hits all the Jimmy Buffett haunts. Teach is a carefree spirit living that “Someday I Will” life—living on the edge, loving fully, and refusing to be bogged down by the mundane. He’s a tour guide by day and a treasure seeker by night. Honestly, isn’t that the Key West dream?
A Tale of Three Timelines
If you think this is just a simple beach read, think again. Chris weaves three different timelines together, which keeps the pacing lightning fast. I’ve heard from so many people that they tore through this book in a day or two because just when things get intense in one era, bam—you’re transported to another.
1. The Present Day
We follow Teach Taylor, who believes he is descended from the infamous Blackbeard. He’s dealing with the weight of that legacy while hunting for a hidden treasure that family lore says was left behind.
2. The Golden Age of Piracy (1700s)
You can’t have a book about Blackbeard’s treasure without the man himself. This timeline dives into the exploits of Blackbeard during his reign of terror (and surprising domesticity—more on that in a second).
3. The Spanish Conquistadors (1500s)
This was the surprise timeline for me. Chris takes us back to the source of the treasure—the Spanish Galleons and the Conquistadors in the New World. It ties everything together, explaining how all that gold got there in the first place and why the pirates were after it.
Chris did his homework, too. He talked about how sometimes he’d write a plot point—like Cortez taking over the Aztec Empire with only a few hundred men by pretending to be a god—and then he’d research it, only to find out that’s exactly what happened. History is wilder than fiction, folks.
Reimagining Blackbeard: Not Just a Scary Beard
We all have this image of Blackbeard: the smoking beard, the crazy eyes, the absolute villainy. And sure, Chris keeps the intimidation factor—Blackbeard was a terrifying pirate captain, after all. But he also humanizes him in a way I didn’t expect.
In the book, you see Blackbeard as a father figure. He’s obsessed with his legacy and his family. He’s got kids all over the place (busy guy), but he feels a responsibility toward them. It adds this layer of empathy to a character who is usually just a caricature of evil.
Chris read a passage during our chat that gave me chills. It described the pirate life not just as crime, but as a Declaration of Independence against the tyranny of the age. These men lived short, brutal lives, but they lived them on their own terms. It kind of makes you look at the “bad guys” a little differently, doesn’t it?
A Cinematic Experience
One thing Chris emphasized is that he writes for the movie in your head. He’s not going to spend ten pages describing the pattern on the curtains. He wants to give you the dialogue, the action, and the vibe, and let your brain fill in the rest.
He describes his style as Pirates of the Caribbean meets National Treasure. It’s dialogue-driven and fast-paced. When I asked him who would play the lead roles if Hollywood came knocking (and hey, Netflix, if you’re reading this, call him), he threw out some great ideas. Maybe Timothée Chalamet for Teach? And Jason Momoa as Blackbeard? I mean, I would watch that. I would watch that twice.
The Key West Foodie Tour (According to Chris)
Okay, you know I couldn’t let him leave without talking about food. If you’re visiting Key West, you need to eat well, and Chris dropped some serious recommendations.
Red Shoe Island Bistro: Chris is obsessed with this place, and now I am too. He mentioned their Grouper (which is hard to find done right on the East Coast) and—wait for it—Lavender Cheesecake. He said it was purple, creamy, and life-changing. It’s a small place with a small menu, which is usually a sign that the chef knows exactly what they are doing.
Santiago’s Bodega: A tapas spot that never misses. Chris goes to the one in Orlando, too, but the Key West location hits different.
Cuban Coffee Queen: Obviously. Chris’s order? You will have watch or listen to find out. Mine?? A Con Leche with two sugars.
Pro tip: You can actually order Cuban Coffee Queen beans to be shipped to your house. I’ve looked into it.
What’s Next for the Pirate Author?
The best news? Son of a Son of a Pirate isn’t a standalone. It’s the start of a series.
The sequel, One Particular Harbor, is already out (yes, another Buffett reference). This one leaves Blackbeard behind and focuses on Captain Morgan.
And he’s currently writing the third book, working title: When the Coast is Clear. He teased that this one brings Blackbeard back as the major pirate and takes some interesting turns. He’s hoping to have it out by the end of the year, so we won’t be left hanging for too long.
Why You Should Read It
Look, there are a million books out there. But what struck me about Chris’s story—and his book—is the theme of legacy. It’s not just about finding gold; it’s about finding out who you are and where you come from.
Whether you’re a history buff, a Jimmy Buffett fan, or just someone who loves a good adventure while sitting on the beach (or wishing you were on a beach), this book delivers.
Where to grab the book:
If you’re in Key West, do yourself a favor and stop by the Key West Island Bookstore. It’s a local gem, and they have a whole section of Florida and Key West authors. Support local!
If you aren’t on the island (sad for you), you can grab it on Amazon.
[Get “Son of a Son of a Pirate” on Amazon here]
(Disclaimer: I am an Amazon Affiliate, which means if you buy through this link, I get a tiny commission that helps keep me in café con leches. Thanks for supporting the blog!)
[Get the sequel “One Particular Harbor” here]
So, go grab the book, pour yourself something with an umbrella in it, and get lost in the adventure. And remember… Someday I Will? ….Make today that day.
