“Gosh, we’re literally down the rabbit hole, aren’t we?” I exclaimed, nonplussed to find myself in a Victorian dreamscape.

I’d just wandered out of the early-afternoon Florida humidity and into The Modern Rose. It’s a brunch spot. It’s also a theme park decorated to invoke a Lewis Carroll novel.

At its “height,” if that’s the right framing, The Modern Rose had several simultaneously operating cafes in Florida, some of which were eventually closed. There are now two locations, one in Delray, where the brand’s existed in one form or another since 2021, and another in St. Augustine, where I was on September 13.

An older couple, sixties I reckoned, waited ahead of me at the hostess stand. They acknowledged my out-loud wonderment with silent, perceptibly patronizing smiles. I could read their internal monologue: “Who’s this rube, what’s he doing here and why’s he wearing a denim jacket near high summer noon in Florida?”

Had they vocalized those questions, I would’ve had answers for the first two. As for the jacket — a John Elliott Thumper Type III with distressing and paint splatters — what could I say? The piece was unavoidably out of place in the muggy, seaside weather. Whether it was incongruous in The Modern Rose’s fin-de-siècle fantasia was debatable, though. I suspect The Hatter might’ve liked it.

After a short wait, I was escorted into one of the dining areas, a small room painted apricot and lit by clusters of white hanging lanterns festooned with bows and polyester roses. A Victorian parlor chair filled the interior alcove of a bay window whose pink drapes were fashioned into a giant bow.

I ordered a $21 avocado toast “flight” — how’s that for inane, boutique-brunch extravagance? — and a 24 oz “Almond Joy latte,” which I’ll confess was the most delicious coffee beverage I’ve ever consumed, bar none.

“So what’s the story with this place?” I asked the server, between toast bites and two-handed sips from what, forgetting the handle, was a bowl of coffee. She was conspicuously reticent. I later learned that The Modern Rose’s original owners had ambitious expansion plans that didn’t quite pan out.

I paid the tab, exited through the looking-glass and gradually found my way back to the Casa Monica, where housekeeping was rushing to prepare a room for a visitor who’d showed up hours ahead of “official” check-in.

I’m an annoyingly self-important guest, even by the standards of high-end hotel clientele. For front-desk personnel, my outward conceit’s made all the more vexing by my travel attire, which conjures an aging Christopher Moltisanti. It’s one thing to be high-hatted by a gaggle of bougie soccer moms checking in for their once-a-year girls’ “vacay.” That’s in the job description. It’s another to feel like you’re being subtly menaced by a wannabe wise guy. (“I know what time it is toots. But there’s $50 in it for you if you can find me a room right now.”)

The Casa Monica desk staff was actually lucky: They got Japanese denim and Loubi Rantulows. Normally, it would’ve been a Palm Angels tracksuit and Air Force 1s.

Whatever consternation I might cause at hotel front desks I make up for at the valet stand, where I’m a hit. The captivation’s most pronounced among younger attendants, who look at me like it’s 1985 in Harlem and I’m Rich Porter. To participate in my peculiar pageantry is, they seem to think, a privilege. It surely helps that I hand out twenties like the other guests do fives, but it’s the collaborative spectacle they relish.

Together, the valets and I build LEGO houses on luggage racks out of Nike boxes pulled from the trunk of German luxury cars, and hang multicolor Louis weekenders from the coat hooks like ornaments. Then we step back, hands on hips, to admire the result, as one might a fully-decorated Christmas tree.

That was the scene in the stone-paved arrival bay at The Casa Monica. “Do you sell shoes?” another guest scoffed, barely able to conceal his open disdain for my traveling circus, which he and his wife were forced to watch while waiting their turn with the valets. “No,” I told him. “I wear shoes.”

The Casa Monica really is nice. The only criticism I could find online referenced outdated rooms, but the front desk proudly informed me that renovations were complete on the upper floors, where I’d be staying. Although small, my room was indelibly charming.

But it’s the lobby at The Casa Monica that stays with you. As the Cambodian bartender at the hotel’s restaurant put it, “I work at an art gallery.” The only blight’s an in-house Starbucks, which feels wholly dissonant and cheapens the experience.

The discordant juxtaposition between The Casa Monica’s stately lobby and the Starbucks it houses is unfortunately mirrored by the downtown area itself, where history fights for attention with shameless attempts to monetize it. Simply put: Downtown St. Augustine’s a conquistador-themed tourist trap.

Locals will agree, forgive me or, if they’re honest, both. St. George Street’s a bazaar of fudge, candy apples and cheap souvenirs. There’s even a Big-style Zoltar machine. If Pigeon Forge is Myrtle Beach in the mountains, St. Augustine is Gatlinburg by the ocean.

I was up extra early — 3:30-ish — on my second day in town. I went out for a bit, came back to the room, fixed a Nespresso and did a little writing. I met my daily macro-market commentary quota by 7:30 or so, leaving a daunting 12 hours until dinner at The Floridian, across the bridge.

I went for a run around the Castillo de San Marcos, came back and took a shower. (Still only 9:15, goddammit.) I sat on the bed and knocked out the last 50 pages of Hesse’s The Glass Bead Game, which I’d been procrastinating about finishing. (Still just 10:15? Christ. Is the humidity slowing down time?) I checked my email and scanned a few Wall Street analyst notes. (11:00. Finally. At least the restaurants are open now.) I threw on a tracksuit — beige Palm Angels — and set out for brunch.

It was hot. Much hotter, I thought, than it should’ve been. Not seven hours ago, down by the water, it felt like 60 with the breeze. Now it must’ve been 90 and it felt like — I don’t know — something a lot hotter than 90. I was sweating in no time.

On St. George Street amongst the tourists and the hawkers I was abruptly overcome by a familiar sense of aimless detachment from the reality of a world I both inhabit and don’t. That feeling — it’s a kind of psychological paroxysm — recently supplanted the outmoded sensation of limbo that used to haunt my consciousness until I succeeded in uniting my past and present in a kind of leveraged, Faustian reverse merger.

By the time I walked into the Roosevelt Room for brunch, I was in thrall to an existential panic. I seated myself at the bar, ordered a tonic water with lime, unzipped the side pocket of my jacket and pulled out a Klonopin.

Maybe it was the benzo, maybe (probably) it was two slices of banana nut bread plastered with cinnamon brown butter, but I felt better after a few minutes. “Do you like working?” I asked the lunch bartender, a homely woman in her fifties who could play Mrs. Claus at a Santa’s Grotto. “You mean here? Working here?” “No, just working period.”

She laughed wryly: “I’d rather not. Why do you ask?” “I don’t know. Sometimes I wish I was –” I paused. I wanted to say “ordinary.” That I wish I was ordinary sometimes, but there was no way to make “ordinary” sound nonpejorative. “What do you do for a living?” she wondered, filling what was on its way to becoming an awkward silence.

“Uh, I run my own business. Businesses. But mostly I just do this,” I said, alluding to the flâneur act that had me chatting with the brunch staff over danish and central nervous system depressants on a random September Monday. “Sounds legend to me,” a younger server chimed in, from the other end of the bar, where she’d been eavesdropping on our conversation.

I ordered a mushroom sandwich on sourdough. It had too much arugula, I thought. Being an avowed arugula advocate, I didn’t know that was possible. The bartender was proud of the food. I didn’t have the heart to tell her it was “mid,” as the kids say. I was still hungry, but didn’t want to let on lest she should foist the corned beef and potatoes on me.

“So what else is decent if I wanted to come down this way tomorrow morning for a snack?” I asked. “Oh, before you leave town you have to try a crepe.” I stared at her blankly. “A MiMi’s crepe,” she specified. “It’s right down the way. You can’t miss it.” 10 minutes later, I was eating a crepe with apple filling in what looked like somebody’s backyard garden.

The rest of the day melted away gradually. By and by it was time for dinner, or time to get ready for dinner. That’s a process. Outfit selection’s no trivial matter. I chose my favorite shirt: A long-sleeve tee from London-based designer Simone Rocha, whose studio might be the only place on Earth with more flowers than The Modern Rose’s dining areas.

For someone whose closet looks like a Saks, a simple piece from Simone Rocha’s an odd choice for favorite shirt. She’s not a big name and you could buy an entire season from her collection for the same price as a couple of Bandoulière 55s. I don’t know what it is about that shirt — it’s all black with photorealistic long-stem roses printed down both sleeves — but I’ve been enamored with it since I bought it three years ago on a whim while researching up-and-coming designers from a downtown loft in Knoxville.

I paired the shirt with white jeans and my favorite shoes: Grey and white Jordan 1 Mids with red accents and soles. Since I was going “all favorites,” I brought along my Explorafunk backpack. Not the one with the tacky spikes. The plain one from several seasons (years) ago. It’s black on the outside, but the inside’s Loubi red. So’s the bottom, just like the soles on the Jordans.

I drove across The Bridge Of Lions to Anastasia Island. After a couple of wrong turns, I found my way to The Floridian, a local mainstay that promises “fresh, innovative, farm-to-table cuisine in a comfortable and casual atmosphere.” Not to be snide, but that’s every restaurant in America in the 2020s. Everyone’s “farm-to-table” and every atmosphere’s “comfortable and casual.”

Salmon with sautéed green beans, cherry tomatoes and a passable attempt at a sauce à la moutarde didn’t exactly count as “innovative,” nor was there anything novel about citrus cured beets with ginger, but The Floridian checked all the other boxes. The food was fresh, it met a loose definition of “farm-to-table” and the ambience was quintessentially “comfortable and casual.” So much so, in fact, that I was decidedly uncomfortable in what counted, for me, as a “casual” dinner ensemble.

Suffice to say The Floridian mostly hit the mark, however generic and clichéd that mark might be. It was “good enough” in a general sense, and also good enough that I came back the next night for small plates at the bar while I waited on a call from G., my long-time right-hand and chief abettor. I was a couple of bites into a plate of eminently serviceable, but wholly unremarkable, fried green tomatoes when she called.

“Where are you?” “Hello to you too,” she teased. “We’re crossing the bridge, where are you?” “I don’t know.” She laughed: “You don’t know?” “I don’t know relative to the bridge, I mean. I’m at The Floridian. I came here last night too, but I’m still not really sure–” She cut me off: “There’s a place called Osprey Tacos right before you get to the bridge. It’s low key. Meet us there.” “Like, on this side of the bridge?” “Yeah, just tell Siri or whatever to take you back to the hotel and you’ll see Osprey on the right just before you’d be going over the water.”

I hung up and asked for my tab. “How far is Osprey Tacos from here?” I asked the bartender at The Floridian. “Oh!” she lit up. “Just go back towards the bridge and it’s–” “On the right just before I’d be going over the water?” I finished her sentence. “Yep. They are so good.”

It was nearly dusk when I pulled into the taco joint. Osprey Tacos is a food truck on a foundation, for lack of a better description. G. and her partner were huddled with a few other patrons in the cramped, indoor counter area. I squeezed in and tapped her on the shoulder. She pivoted. “Haaaaay!” she trilled, flinging her arms out for a hug, heedless of the close quarters. She introduced her partner, who’s deaf.

We ordered, went outside and sat at picnic tables arranged under a large awning. We made small talk while we waited on our food. G. facilitated, signing to her partner and translating her partner’s signing back to me. Our food came. The tacos were the best meal I had on the trip.

When we were done we made our way to the cars. “Thanks for taking care of her,” I told her partner, who apparently didn’t need that translated. She made prayer hands and went around to the driver’s side of their SUV, leaving G. and I to wrap it up.

I opened my trunk and produced a new handbag. “A token of my appreciation. It’s Stella McCartney.” “Oh my god, is that the?–” “Yep. The vegan ‘leather,’” I told her, making air quotes. “That bag’s 100% cruelty-free.” (When I gifted her a Gucci wallet in July, I’d forgotten that leather accessories run afoul of vegan sensibilities.)

She hugged me again. We lingered a minute in the failing Florida sun. “So, you gonna write about this trip?” she wondered, with a chuckle. “Yes and no,” I said. “Do they get it? Your readers? Like –” she trailed off. “Get what? The big picture you mean?” “Yeah,” she said. “Yes and no,” I said again. She nodded, her lips turning up in an oblique smile: “Legend.”

The Floridian

Casa Monica Resort & Spa