Years ago, Dr. Beach declared Siesta Key the No. 1 beach in America. And that, friends, was the original hit. That was our gateway accolade. Because once a region gets a taste of being No. 1 at something, it does not stop. It cannot stop. Just ask any ‘Waterfront Specialist.’
—It happened again. I was standing in my kitchen, minding my own business and eating a grouper sandwich — and there will be more on the grouper sandwich later, because in this town there is always more on the grouper sandwich — when I learned that Longboat Key had been named the 9th Best Island in the Continental United States by Travel + Leisure magazine.
—Ninth. Best. Island.
—Now, a lesser community might read the word “ninth” and feel a flicker of insecurity. A lesser community might ask: who are these eight islands ahead of us, and can they be reached by boat, and do they have any idea what we are capable of? But we are not a lesser community. We are a community that collects Best Of awards with the calm, methodical enthusiasm of a raccoon working its way through your patio furniture, and we are not about to start apologizing for it now.
—It All Started With a Man Named Dr. Beach
—For those of you new to the area — meaning you closed on your condo sometime after lunch — allow me to explain how we got here.
—It began, as these things do, with a man named Dr. Beach. Dr. Beach is a real person with a real doctorate who ranks beaches for a living, which I mention because somewhere out there is a guidance counselor who once told a young man that “Beach Ranker” was not a viable career path, and that man is now Dr. Beach, and I hope he sends her a postcard.
—Years ago, Dr. Beach declared Siesta Key the No. 1 beach in America. And that, friends, was the original hit. That was our gateway accolade. Because once a region gets a taste of being No. 1 at something, it does not stop. It cannot stop. It goes looking for the next ranking, and the next, until one day it wakes up as the 9th Best Island in the Continental U.S., surrounded by empty award ballots, telling itself it can quit anytime.
—Every Realtor Here Is No. 1, Which Is Statistically Fascinating
—I should note, purely in the interest of journalism, that this region contains roughly 4,000 luxury realtors, and every single one of them is the No. 1 Luxury Realtor. Every one. They are all also, simultaneously, in the “Top 1% Nationwide,” which means that our local Top 1% appears to contain approximately 118% of all realtors, a mathematical achievement I believe has never been matched anywhere on Earth, possibly including in physics.
—And they do not stop at No. 1. They cannot stop, because if one of them is merely No. 1, the next one has to be No. 1 Platinum, and then the one after that is No. 1 Platinum Diamond Elite, and then it’s Chairman’s Circle, President’s Council, Founder’s Club, and eventually, I assume, Supreme Galactic Overlord of Closings. It is an arms race of self-issued superlatives with no ceiling and no shame, conducted entirely on the backs of bus benches.
—Because that is where they live now: on things. Their faces are on bus benches, on shopping carts, on the sides of buildings, and inside glossy magazines roughly the width of a cinder block that arrive in your mailbox uninvited, each headshot featuring the same crossed arms, the same power blazer, and teeth so aggressively whitened you could use them to land a small aircraft at night. And every few weeks one of them mails you a postcard that says “I JUST SOLD YOUR NEIGHBOR’S HOME!” as though this is happy news, when in fact, given what it does to your tax reassessment, it reads less like a greeting card and more like a ransom note.
—We Have Also Decided the Answer to Every Problem Is Another Roundabout
—Which brings me to how we get around here, or, more accurately, how we go in circles.
—At some point, the greater Sarasota area concluded that the solution to every intersection, every disagreement, and possibly every unresolved geopolitical conflict was a roundabout. We are now building roundabouts faster than we can build the signs bragging about how we’re paradise. We have roundabouts downtown. We have roundabouts on the bayfront. We have roundabouts leading to roundabouts, and I am fairly confident that by 2030 we will unveil the region’s first roundabout located entirely inside another roundabout, at which point traffic will simply orbit the bayfront forever, like a very expensive, very tan asteroid belt.
—And the roundabout is, philosophically, the perfect monument to who we are. You enter. You circle. You commit to absolutely nothing. And eventually you exit at precisely the spot where a nice man in a blazer can sell you a condo.
—Of course, the roundabout only works if everyone agrees to yield, and here we run into a problem, because a meaningful percentage of our seasonal population regards the word “yield” as a direct personal insult. You know the maneuver. The car eases halfway into the circle, blinker on, and then stops dead — fully committed to being uncommitted — awaiting, apparently, further instructions from God. Meanwhile you are on your third full lap around St. Armands Circle, because you missed your exit the first two times, because you were reading a realtor’s face on a bus bench. Everything in this town connects. That is the magic of the place.
—Now There Is a Hotel Where You Can Hang Out With Stingrays
—Naturally, the awards have escalated. We now have the St. Regis Longboat Key, which opened in 2024 and was promptly named the second-best new hotel in the entire South, presumably by judges who were then gently escorted into its 20,000-square-foot spa and never heard from again.
—The St. Regis features multiple pools, cabanas, a winding waterway, and — and I want to be very clear that I am not making this up — an “Under the Sea lagoon experience” featuring stingrays, tortoises, and tropical fish. So we have officially reached the phase of human civilization in which a hotel is no longer considered competitive unless you can, at check-in, elect to swim with a stingray. I do not know who asked for this. But I know that somewhere in that lagoon is a man who paid $2,000 a night, looked a tortoise dead in the eye, and thought to himself: worth it.
—Which Brings Us Back to the Grouper Sandwich
—And then there is CNN, which just this month named Sarasota the No. 1 Best Town to Visit in all of America, singling out our restaurants for particular praise. Longboat’s own Dry Dock Waterfront Grill got the full CNN treatment, with the network specifically advising visitors to order a grouper sandwich, sip something cold like a Hugo Spritz, and admire the egrets stalking the breakwater.
—I want to focus on that egret for a moment.
—Do you understand what it means to have your local wildlife written into a national CNN travel recommendation? That egret is now, functionally, an employee. That egret has a stakeholder. That egret cannot simply be an egret anymore — standing on one leg, contemplating the void, doing normal egret things. That egret has to show up. That egret has to stalk the breakwater on brand and on schedule. And frankly, given the several thousand dollars a night people are paying to stand near it, that egret is dramatically underpaid, and if it had any sense it would unionize with the tortoise.
—At This Point We Are Winning Awards That Haven’t Been Invented Yet
—We are, by now, so thoroughly and relentlessly acclaimed — Best Beach, Best Town, Best Island, Best New Hotel, Best Grouper, Best Bird-Adjacent Alfresco Dining Experience — that it has stopped being news and started being weather. Somewhere a computer server is scouring the internet as we speak, and it has already concluded we are Paradise. The AI has decided it. The AI’s boss has decided it. And by next Tuesday we will be formally named the No. 1 Place to Open a Checkbook and Quietly Weep With Joy, and we will put up a sign, and we will not take the sign down, because around here we never take the sign down. I remember when the old Colony Beach & Tennis Club was named the No. 1 tennis club in the country, and that sign stayed up long after the tennis did, in a display of civic commitment I personally found inspiring.
—There Is Exactly One Critic Left
—There remains, of course, one entity that has stubbornly declined to give us an award, and that is Mother Nature, who prefers to submit her reviews in the form of hurricanes — typically arriving the same week we finish hanging all the other signs. She is the only critic in the region who cannot be reached for comment, cannot be sold a sponsorship, cannot be seated near the breakwater, and cannot be talked into yielding at the roundabout. Every summer we squint nervously at the Gulf and pray that this year she gives us, if not a rave, then at least a polite miss.
—But barring her opinion, the news could not possibly be better. We are the 9th Best Island in America — which means we are also, unofficially, the 9th Best Island in the known universe, because nobody has surveyed the other planets yet, and I, for one, like our odds.
—So put up the sign. Leave it up. And if you’re new here, welcome. The grouper’s terrific, the egret is contractually obligated to be present, a tortoise in a lagoon is quietly judging you, and there are four thousand No. 1 realtors who would love to talk — just as soon as you finish this lap around the circle.
—We wouldn’t have it any other way. And we’ll keep saying it, too — on the signs, on the bus benches, over the roar of every last roundabout — until the tape finally wears clean through. As John Lennon said, right before the whole thing dissolved into beautiful, unhinged noise: “Number 9. Number 9. Number 9.”
