Caroline Calloway weathers Hurricane Milton in Sarasota

Caroline Calloway by Caroline Calloway.
Photo: Caroline Calloway.

In the hours before Hurricane Milton made landfall, an unexpected sideshow emerged that has the potential to devastate many populated areas on Florida's east coast. Caroline Calloway, the influencer, author and storyteller who now lives in Sarasota, posted on social media that she would hunker down in her waterfront condo to wait out the hurricane, which will more or less directly hit her city with a deadly storm surge of up to 15 feet.

Many people joked about her decision, which defies the advice of Florida officials who consistently say people will die if they stay in evacuation zones like theirs.

Assuming this isn't just a publicity stunt, I spoke to her on Wednesday afternoon to get clarity on her plan.

Hello, we just wanted to know about your decision and perhaps politely encourage you to reconsider your decision. But I was wondering why you decided to stick it out for Milton?
I made the call a few days ago after a hurricane hit our building.
I have two friends coming to stay with me and my mother just arrived here. Our building closes at 7pm, so we have a lot to do.

I don't think people understand the reasons why I stay, and I'd like to clear that up with you, starting with this viral tweet that's doing the rounds. I never said I lived on the ground floor. I live by the water, but I live three floors up. Even with a 20-foot storm surge, I won't see any of it. Secondly, I never talked about it online and didn't really plan to because it was pretty traumatic. But I recently mentioned it on my Instagram story and now feel compelled to elaborate. I mean, unless, God forbid, new York The magazine published something very snarky about why I'm not going. Even though we know it new York The magazine would never do that.

No joke here, no.
OK. Well Matt, you damn well better give me something to live for.

Act.
That's entirely up to you. I'm kidding. My sense of humor is very dark, and perhaps you should turn that into a disclaimer. I feel like some people think I'm very stupid because I say everything without irony. An example that particularly comes to mind today – because Ziwe just texted me – is when I said I wanted an ally cookie on her show. I thought, That's my sense of humor. It's just very superficial.

What did she write to you?
She sent me a link to a local animal shelter, which was shocking because I thought she wanted me dead.

Again I'm joking. I don't really think she wanted me dead. She is a very nice artist.

So why Are Are you staying?
Okay, my reasons for staying are Hurricane Ian, which hit in 2022. I was evacuated to my mother's house in Northport. She lives very deep inland, but it's very flat and I'm three stories higher than her house. It was three days, no water, no electricity, no air conditioning, which is a huge problem in Florida in late summer and even early fall. We were evacuated by boat by the US military. Their entire neighborhood was flooded. They rode one of those Lana Del Rey husband fan boats down the street that used to be known as her street.

The worst part wasn't our dwindling food supply or the insects, which were frankly terrifying as all of the surrounding land became even swampier than rural Florida. I hope you never find out what was actually the scariest thing was at night when we heard shots. I still don't know if it was just drunk Floridians exercising their Second Amendment rights at a homemade shooting range in their backyard to pass the time, or if it was something more sinister.

The other 50 percent of the decision is because grandma moved into this condo building in the late 70s. I have been coming to Sarasota since I can remember visiting. And that means we have a lot of family friends in the building who are very old. These are all friends of my grandmother that we inherited, so to speak. With the money I made, I would never have been able to afford a down payment cheatereven though it sold so well. The only reason I was finally able to make my first real estate purchase was because friends and family were selling it, we got such a great deal, and we are so deeply rooted in this condo building, so to speak. My old friends – Ruth, Terry, Holly and her mother Maryanne – are all staying and someone has to check on them.

How many floors does the apartment have?
It has 16 floors.

Listen, I don't think any of these reasons alone would have been enough to evacuate. I'm not a first responder. I'm bloody Caroline Calloway – I don't want to be anywhere near an emergency! I'm useless. That's why I don't think I'm the best person to help them. But given the very painful experience I had during the evacuation with Ian two years ago, the two reasons together were definitely enough to motivate me. Combined with the final reason of the general safety of our building. In all the years my family has lived here, there has never been a flood. The windows have never been broken. I know our windows can withstand gusts of up to 145 miles per hour. Every condominium in our building is also enclosed. Just because we're on the water doesn't mean all your rooms face that direction. We have many safe rooms that consist of thick concrete walls.

Have you considered the possibility that you would have to be evacuated from your apartment and that this would be some kind of continuation of that terrible Ian experience?
It's just a choice between so many terrible options. It's like, okay, so we get evacuated here, but then we left all our neighbors behind. And we will also get stuck in traffic. I can't drive. Remember, I'm a real human being, I spent my last 20s in either England or the West Village. I never got a driver's license, so I would have had to wait for my mother to come and make me evacuate, which would have really put us behind in traffic. So we were in traffic in a hotel that was also tropical. I doubt we would have made it out of Florida State in time assuming we couldn't have left until Tuesday morning, I think that's probably the earliest she could have come and picked me up. So is it just like that? We would be somewhere else in the state, in a less stable structure and with less terrible weather, but what would you choose without our neighbors? It's all very difficult and that's what I chose.

Why are your mother and two of your friends staying with you in the heart of the place where the hurricane will make landfall?
It's really about the security structure of this building compared to where they left it. My mother lives in Northport in a small house, parts of which are much more likely to be badly damaged by flying debris. I'm in a million-ton concrete tank of an apartment building; Our roof won't fly away.

What is your disaster plan? Do you board up windows?
We have hurricane windows for winds up to 145 miles per hour. We'll record them, but we won't get in. But a flood gate is being constructed in our condo building, which is why we have the 7 p.m. closure deadline.

But my biggest plan for the hurricane will be very similar to that of the last large-scale disaster, COVID-19.

I felt then and now that there were many qualified experts and activists with social media and large social media presences providing incredible resources, incredibly reliable resources – and that I, Caroline Calloway, provided the best service in these difficult times Anxiety and high stress are entertainment. I think my most important goal in this world is to make books. However, I believe that online performance art and entertaining others are a close second. So obviously my plan for the hurricane is to stay safe, fill up the bathtub, charge chargers, etc. But I want to try to entertain. I didn't just get so into it that I almost died. This was an informed decision by an adult for a variety of reasons.

I've been conducting interviews all morning and literally preparing for the hurricane, so I haven't given this content the attention it deserves yet. I wish I could tell you more about what that will be, but I know I will do something. I'm going to do what I do best, take a great piece of luck and turn it into a great content opportunity.

What about food? What else is on your preparation list?
I'm going to cook a lot of pasta so we can have those and the tapers ready, and also fry some dumplings. And then my mom did most of our shopping together, but I have food for about three days, but no longer. My mother brought most of the non-perishable foods.

Was there direct contact from the district or state?
No, but Emma Roberts somehow got my phone number and wished me well. So I would take that any day.

People have been paying attention to the story of you huddling. I just saw one post It says: “Caroline Calloway's refusal to leave a mandatory evacuation zone (right on the water, right where landfall is expected) and die in a hurricane would honestly be the perfect ending to her narrative.” I was wondering what Do you think about this type of thinking?
Totally agree. I think it's a very funny joke. It almost hurts your nose. Like when Eve Babbitz literally set herself on fire. However, I would like to point out that this did not kill Eve and this hurricane will not kill me either.

I really hope you can rub this in our faces, all of us worried people in New York.
I don't have to rub it in your face. Just plug in my damn book.

This conversation has been edited for length and clarity.