Never Become a Travel Expert

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Okay, we’re back! I’d planned to send this out on Monday, and then, well, I got distracted. For a few days. But here we go again, once more sponsored by the good folks at Authory, whose automated portfolio system for writers is one I subscribe to and endorse myself. Click their ad, and I get $2!

Key West is chickens. Their feathers are green and blood red and earthy orange, and they glisten with the sheen of a computer simulation. The chickens are everywhere, clucking in parking lots, crowing at dawn, crossing the streets with their adorable broods (and prompting the inevitable jokes¹ ), battling one another for territory, roosting on railings after dark all curled up into deceptively feline balls of bird. They are mysterious, although there is no great mystery: They are survivors of the kitchens and cockpits of Key West’s past, now enjoying the coopless freedom Key West seems to offer all who are willing to journey to and squeeze themselves into this little island, the last in a chain of little islands, that is the southernmost point in the United States.

No. I didn’t want to start with the chickens. The chickens were too obvious. They’re among the first things any Key West tourist notices, which also include: the aerial views as your plane swoops in for a landing, the shallow clear green water stretching out in every direction, pocked with sandbars and riven with scars in the rock where ships tried and perhaps failed to land; the town’s absolute dedication to drinking and fishing but mostly to drinking; the popularity of the word southernmost as a marketing term, because there’s nothing tipsy tourists like more than contemplating geography; the popularity of conch as a marketing term² , even if many (but not all!) Key West cooks seem to want to turn the iconic mollusk into shreds and fritters as flavorless as industrial chicken breast; the popularity of Hemingway as a marketing term (business idea: the Southernmost Hemingway Conch Bar!); the symphony of human voices and accents that surround you—Haitian Kreyòl, Jamaican patois, old-time New York, and every shade of Spanish.

All of these are easy and obvious. Key West clichés—tropes you’ll find in any and every article about this (ahem) 5.6-square-mile island of 25,000 residents that’s just 90 miles north of Cuba. They’re not the kind of thing that I, a veteran travel writer after all, really want to launch an article with. Is it not my mission—nay, my sacred duty—to present you with a view of a place that is surprising, that makes you see a destination you thought you knew in a fresh, unpredictable way? Maybe, I thought, maybe the chickens is it!

But is the chickens it? You’ll have to tell me because I can’t tell anymore. I spent five days and four nights in Key West, and I can tell you everything about the place and nothing about the place. I spent loads of time walking through narrow streets that smelled of saltwater and wood, where Sycomore figs consumed fences and shotgun shacks gave way to newly built, ready-to-Airbnb $3.7 million homes, and I also spent loads of time shuttling back and forth in Ubers and Lyfts. I feel like I know the place, and I feel like I’ve barely begun to penetrate it.

And that’s because I was there with, and for, my entire family.

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The Grosses—11 of us in all—went to Key West for my father. Mid-February marked his 80th birthday, and he (and my mom) wanted to get out of the Massachusetts winter to celebrate somewhere warm. The French Caribbean, maybe? The non-French Caribbean? Bermuda? San Diego? (San Diego, seriously?)

Key West, we decided in the end, would be an easy flight³ for most of us, and it would have excellent weather, lots of fresh seafood, and—equally important—specificity. This wasn’t just any touristy beach town—Key West was its own weird place, with a history that encompassed Harry Truman and Ernest Hemingway, the Cuban Missile Crisis and the Mariel Boatlift, Jimmy Buffett and gay liberation, cigars and rum and the U.S. Navy. I don’t know why we need these highbrow details grafted onto a milestone birthday vacation, except that I do know: We’re overeducated liberals who, in another beach town, one devoid of such curiosities, would feel bored, aimless, lost. We need to be in a place that has an existence beyond our brief encounter with it, or else we haven’t been anywhere at all.

This may all, I am fully willing to admit, apply solely to me.

So I arranged it. I booked a property in Old Town Key West: a beautiful house from 1951—the Truman era!—with a modern, updated interior, a jungly garden of 30-foot travelers palms and white orchids, and what we were told was one of the biggest private swimming pools in the city. I researched private chefs and hired one for the big birthday dinner; the menu ranged from conch ceviche and smoked wahoo to cut-up salad, Cuban pernil, and Chilau-style spiny-lobster stew. I hit up my friends Nathan Thornburgh, a fourth-generation Key Wester, and Cheryl Tan, who spends a lot of time there and has written about it for the New York Times, for recommendations, then dutifully assembled them into a Google Map.

If I were writing this as a service piece for, say, the New York Times, I would have to explain in depth how I did all of this, but it’s not complicated: I googled things like “private chef Key West” and “vacation rentals Key West.” I read all the results, noted prices and appealing or unappealing details, and put a selection of the choices onto the Gross Family’s #keywest2025 Slack channel for everyone to weigh in on. Then I booked everything with my own credit cards and bank accounts, and my siblings and mother reimbursed me their shares via Venmo, Zelle, and even a handwritten check⁴ . It can be daunting to do all this travel booking, I know, but after you’ve done it, oh, a couple of hundred times because it’s your job, it’s no longer stressful. Well, it’s less stressful. A little.

Whether you like booking vacations for your nearest and dearest or not, this is your fate if, like me, you become a travel expert. In my family, both immediate and extended, and often in our circle of friends, I’m the guy who makes the plans. It seems natural, right? I spent years and years writing travel stories for the Times, Afar, Saveur, Bon Appétit, Airbnb Magazine, Food & Wine, and Businessweek, and I made it my business to dig up cool hotels, under-the-radar restaurants, new airline routes, and, in general, affordably transformative experiences. If I were your son, your husband, your brother-in-law, your close friend, you’d probably want to have me in charge of booking the big vacation. And in truth, I want me in charge of the booking. I know how to do this stuff—how to find the deals, avoid the scams, uncover the overlooked, seek out options to suit every individual traveler, schedule our days and nights, and package it all up in emails, Slack messages, Google Maps, and more so that everyone can know what’s going on without having to ask me. And still they ask me, because I’m the travel expert, and I’m happy to hand out the answers and the links and the calendar reminders, because I do enjoy being the travel expert.

What’s more, I know I’m going to do it correctly. I’m not going to book the wrong place on the wrong dates, or miss out on a fantastic deal, or get eleven people a rental home with just two bathrooms. That’s not to say I’m perfect, but I’m experienced. I’m probably going to get it right.

And on top of all that, I might even have one or two issues with control! Because I’ve done all of this so many times, I’m not about to allow someone else to step in and do the planning in my place, because do they really think they can do it better than me, the self-anointed travel expert?

(Here’s where I feel like I need to add a clarifying message about all this and repeat the Gross family motto. All together now: It’s not a criticism—it’s an observation!)

But as much as I enjoy being the travel expert—and those of you in a similar position may feel this, too—it’s also a burden. Despite the years of practice, planning a trip takes a lot of work, a lot of time. It’s not just the research and booking: It’s the coordination among everyone who’s participating, figuring out when they’re available, what they want to do on the trip, what they absolutely DO NOT want to do on the trip—every minor preference and peccadillo of, in this case, nearly a dozen travelers ranging in age from 8 to 82. To be clear, they’re not that challenging a group! No one was difficult, no one was unreasonable. Still, it’s a lot of people to take into account.

And, of course, planning was only the beginning. Once we had made our way to Key West, then I, the one with every facet of the trip in his head, had to take care of everyone—to guide them, to herd them. (Maybe I didn’t have to, but someone did—so it was me.) Bringing a large group to a new place means shopping for groceries so everyone can eat the breakfast and snacks they like, locating the closest beaches, and figuring out how to get everyone to and from a restaurant for dinner. (We walked! Eight of us that first night snaking 30 minutes through Old Town, our snake growing ever more diffuse, its head reaching the destination several minutes before its tail.) As the days passed, we had to contend with a dozen different waking, sleeping, and exercise routines, which shifted how and when we could all leave the rental property—as a group, as a family—to go, you know, do things, like visit the Florida Keys Seafood Festival, where we gorged ourselves on stone crab legs and shrimp in the raw naked sun, and the Hemingway Home & Museum, where we learned far more about six-toed cats and the digging of Papa’s swimming pool than about, say, how Key West influenced For Whom the Bell Tolls. Sure, there were times when we split up into smaller groups, twos and threes and fours off on their own subquests. (At Books & Books, I met Judy Blume⁵!) And it’s not like we were on some schedule, with a list of activities and sights that needed to be checked off so that we could feel we’d had a satisfactory Key West vacation. But still, it took some energy to keep this sprawling group of loved ones shuffling forward, toward some wonderful communal experience. In the end, we spent a lot of time at the rental house, eating, talking, swimming, reading—just hanging out.

From time to time, I wondered what it would be like on the other side of this, to be on a vacation planned and executed by someone else. To go where someone else chose, to eat whatever they prepared⁶ , to follow along through group activities and not to spend my spare leisure minutes rebooking flights home ahead of a storm, or researching whether I could safely use travelers palm leaves to grill a wahoo filet (I can! I did!). To not worry at all about where we should be or what we should do and just be and do whatever I want. What would that be like? Would I even enjoy it?

Honestly, I don’t know that I would. Because while all of what I’ve written above may sound like an extended kvetch, a luxurious burden about which it is in profoundly bad taste to complain, I think of it more as a responsibility, one I’m glad to embrace. And that’s because the reward for my efforts was to see the people I love not only happy but happy together. They were swimming in the pool together, eating scallop ceviche and fresh guacamole together, hunting for trinkets and gawking at Duval Street drunkards together, walking through sleepy streets in search of smoothies together, staying up late and talking about everything and nothing together.

And it wasn’t just they, it was we, for I was there among them, partaking of their happiness as if it were my own—which it was. I was happy. Even though the travel-writer part of my brain was screaming that I needed to see and do more to make sense of Key West, I was happy. Even though I wanted to find a couple of hours to hide in a corner and read a novel, I was happy. Even though I didn’t get enough time in one of the biggest private pools in Key West, I was happy. My dad was turning 80, and we’d flown in from New York and Seattle and Pittsburgh and Boston to celebrate together, surrounded by chickens and Parrotheads, pickliz and puerco, at the far ass end of America, and he was happy, so we were happy, so I was happy.

And maybe, when I turn 80 myself, I’ll be ready to let someone else plan my party. Maybe. 🪨🪨🪨

It’s Good (?) and I Like It: Key West (the Sitcom)

This Fox comedy from 1993—brought to my attention thanks to my brother, Steve—stars Fisher Stevens, Denise Crosby, and Jennifer Tilly, and lasted a whole 13 episodes. It’s… something!

Read This Thing I Wrote for Inverse and FERN

Sometimes I still write professionally, or at least for other publications:

1  Why did the chicken cross the road? To get to the other side! Why did the squirrel cross the road? Because it was stapled to the chicken!

2  They pronounce is conk, which isn’t that surprising, but when you’re traveling in the lands where they eat it—the Caribbean—the pronunciation can change from place to place. Conk or conch? is one of the first things I always ask.

3  In theory! In reality, winter storms in the Carolinas mucked up almost everyone’s flights.

4  Thanks, Mom!

5  Yes, I handed her the printed edition of Trying!

6  Props to my sister, Nell, who woke up early every morning to make coffee for everyone.