The richest guy in the world at the time, that you've never heard of
Peter Brooker, November 2025.
St. Augustine, Florida
Every member of staff in The Casablanca Inn either was, or cut the shape of being mournfully hungover. One waiter even took our order wearing sunglasses, no doubt to shield the scrutiny I would involuntarily glare upon him. It occurred to me that they were perhaps all getting high on their own supply, as the Tini Martini Bar is attached to the hotel, and is one of the greatest sought after spots on George Street on a Friday night.
Tini Martini Bar at the Casablanca Inn, St. Augustine, Fl
Myself and Anastasia were also dulled that morning by the excess. The Tini Bar didn't just serve Martini's, but the menu of Martini Cocktails was exhaustive. And with each, the customer is presented with a serving shaker that holds two, not one, Martinis. "I've seen people fall off their chair after two of these and not get back up!" the headwaiter Chris said. He had a low drawl, the obligatory arm tattoos, and the general disinterest of a man that could hustle harder for tips, but preferred not to.
The old adage that middles are the only good thing about all things, be it a film, a relationship, etc, has never been more true than that of a Martini. The upside triangular conical shape of a Martini glass, teleports through the few glorious opening gulps, directly to a misley sorrowful swill. But with this Martini shaker, there is room for one more serving. And that's the fantastic middle a true Martini drinker craves, the realisation that there is a refill, without the wait or downpayment.
The best way to see the town is on the Trolley Tour. There is no need to book online as every hotel will be able to supply tickets, saving you countless emails and feedback requests from Booking.com and Viator, etc.
The back roads are thronged with locals pushing their service dogs in prams, some homeless but very few, and there is always a smattering of people dressed as pirates. As the evening winds on the locals get Key West-drunk. These are some of the oldest roads in America, and I'm sure they've encountered their fair few puke piles, even before the Ponce De Leon became a college.
Off Palm Row a lady had fallen off her segue and laid strewn in an inconsolable heap. Even though it's 2pm, the chances of her accident being drink induced, is still top billing in my mind. It would have made a great photo, but I didn't take the shot out of deference. We've all been there.
Bridge of Lions, St Augustine, Fl
Our driver was Pepper, an eccentric woman who told every joke like it was the first time. "I'm Pepper, ready to ride the trolley? Buckle up, here we go!" On the main strip that runs past the Fort - which has successfully fended off 10 minor attacks and two big ones over the years - past the Casablanca Inn towards the bridge with the lions carved from Carrara marble which welcomes commuters, there is a gang of Harley Davidson riders, the most obnoxious of all vehicles as they spill out their din of heavy metal from their stereos.
A tour of the Old Jailhouse was most impressive. The barracks made Alcatraz look like the St. Regis. Only unlike Alcatraz, no prisoner had made an escape. Some prisoners that were condemned to death had to build their own barracks to be hung from. A sign in the barracks read;
"Repeating, I am sorry for my crime and am ready to stand before my God. Sim Jackson shot downward through the scaffold trap at 11:15 this morning in expiation of the crime of wife murder (the tour guide refrained from elucidating any further on the murder as children were present, but he made various side-whispers that it was an incredibly horrific murder).
At one of the hangings, Doctor Alexander (according to a pre-arranged plan), interrogated a dying man at short intervals for the purpose of ascertaining how long consciousness remained and if the man was suffering pain. He told Jackson to close his hand if he heard him. The fingers immediately closed. Then, he told him to again close his hand if he was suffering much pain. The hands which had reopened again closed, but after that no response was obtained. Death ensued in ten minutes, and the official announcement of death was made in fourteen minutes after the trap dropped."
At one of the hangings, Doctor Alexander (according to a pre-arranged plan), interrogated a dying man at short intervals for the purpose of ascertaining how long consciousness remained and if the man was suffering pain. He told Jackson to close his hand if he heard him. The fingers immediately closed. Then, he told him to again close his hand if he was suffering much pain. The hands which had reopened again closed, but after that no response was obtained. Death ensued in ten minutes, and the official announcement of death was made in fourteen minutes after the trap dropped."
Flagler college
Flagler College - named after William Flagler, who the tour guide called the richest guy in the world at the time, that you've never heard of - was previously a luxury hotel called Ponce De Leon.
Flagler, who'd made his money in oil, honeymooned in St Augustine only to find the town not befitting of his needs. He spent one night and returned back to New York the next day. However, he saw the town's potential and he could bring his sick wife to the local springs to convalesce from her ailments. As a consequence he built this hotel (The Ponce St. Augustine Hotel), and some years later a casual hotel opposite which is now the Lightner Museum.
Osterley Safety Razor at Flagler College, St. Augustine, Fl
The college was built in the Gilded Era style and it's free to walk in the lobby, where you'll walk across a hand-laid African mosaic tiled floor sheltered beneath an ornate wooden rotunda, furnished with paintings reminiscent of how Klimt would paint his women. If you pay for the tour you'll get to see inside the dining room, lit by lion head sconces, a new chandelier which was a replica of the old one that was taken down by Flagler after the wretched feedback his patrons gave him. "Too ugly", they scorned.
The room is bathed in natural light that seeps through the 79 stained Tiffany windows which give it an ethereal quality.
"Anyone get kicked out of this place?" I ask the young guide.
"Excellent question," she said with a tip-winning smile. It was a good question, although that was a response to everyone on the tour who had a question, some of which were terrible questions such as; "How many people can eat in this dining room?"
"There was a food fight in this canteen once. It kinda got outta hand and one girl chucked a bowl of tomato soup. They kicked her arse out."
Restaurants
La Nouvelle is an out of the way French restaurant, also a small Airbnb. This was Anastasia's favourite restaurant of the weekend. We both ordered the Duck, but Anastasia declined to eat the Duck Fat Potatoes. I asked the young waitress Angelica what's the craziest thing you've seen in this town? "I saw a guy throw up in Prohibition Kitchen once," she said. In fairness, I had put her on the spot. (Note to self, ask this question at the start of the meal and not when paying the bill, giving them time to toil over the question).
Catch 27 has a serviceable menu and has outdoor seating. Anastasia had the risotto and I forgot what I ate, how spoiled I am.
Old City House Inn ...again can't remember what I had, but Anastasia had the Veal and it was sublime. It's too bad that Americans lack the ability to talk in hushed tones. The party of ten on the table adjacent to ours were far too convivial and we had to endure their raucous benign conversations rather than our own. The lighting is also too clinical.
Salmon supper at River & Fort, St Augustine, Florida
At the River & Fort the chips looked permanently frazzled, poor things. Luckily I opted for the salmon which was commendable. The young ginger haired waiter made unnecessary chit chat, and bragged about how he could drink ten bottles of Corona without getting drunk. Which is not totally inconceivable given the self-confessed 'size of him'. I desperately whirred through the files in my mind to rebuke his honest appraisal, but instead of a cliched 'you're not fat,' I blurted 'don't worry, even the grass is fat in Florida.' Which is something Anastasia remarked upon earlier, the grass is indeed fat in Florida.
Activities
The Old Retail Store
A small museum which would be forgettable had it not been for the tour guide, a young gentleman, (a dead ringer for Rob Schneider) who Anastasia much preferred to me. Also a litany of old typewriters on display. Oh how I regret giving mine away.
Villa Zoraida Museum
This Historic Gilded Age Home Museum is situated opposite The Flagler College. Cluttered, not furnished like a Chinese flee market, especially with all the Christmas decorations. The Moroccan style is not my thing, all the woods are too dark to admire. They do lay claim to having the oldest rug on display in the U.S., 2400 years old and said to be made out of real Egyptian Cats, which meant bad luck to anyone that walked over it.
River Boat Tour
Worth killing a couple of hours with an outdoor activity. Dolphins were seen at a distance. A spinning shark was sighted but not by me. By the mouth of the inlet there is a small beach which is accessible by car. Typical Americans need to have their 4x4's in sight no matter where they go. The last house on the beach is worth 4 million and both the tour guide, a funny grey haired lady, and I, agreed that living so close to those irritants would be a combustible nightmare.
Osterley Safety Razor, St. Augustine, Florida
About the author
Peter Brooker is the co-author of From Tailors With Love an Evolution of Menswear Through the Bond Films and is also Editor-in-Chief of From Tailors With Love, a blog, vlog and podcast dedicated to men’s costumes and cinematic style.
Follow Pete on Instagram: @therewillbebond (over 22k followers)
Follow Wilde & Harte on Instagram: @wildeandharte (2k followers)
Above: Pete with his Osterley Safety Razor.
