Why Caroline Calloway Is Staying Put in Sarasota for Hurricane Milton

An unexpected side plot has emerged in the hours before Hurricane Milton lands with the potential to shred many populated areas of the western Florida coast. Caroline Calloway, the influencer, author, and raconteur who now lives in Sarasota, posted on social media that she would hunker down in her waterfront condo to wait out the hurricane, which is expected to make a more or less direct hit on her city with a deadly storm surge of up to 15 feet.

Many people began joking about her decision, which defies advice from Florida officials, who keep saying people will die if they stay behind in evacuation zones such as hers.

Caroline Calloway refusing to leave a mandatory evacuation zone (right on the water, right where landfall is expected) and dying in a hurricane would be the perfect ending to her narrative tbh pic.twitter.com/VBrVqD6LeC

— sydney (costume wearer) (@itsoolongshot) October 8, 2024

Assuming this is not just a publicity stunt, I spoke with her on Wednesday afternoon to get some clarity on her plan.

Hi, so we just wanted to check in about your decision and maybe politely urge you to reconsider your decision. But I was wondering why you’ve decided to stick it out for Milton?
I made the call several days ago after our building had a hurricane meeting.
I have two friends that are coming to stay with me, and my mom just got here. Our building is locking down at 7 p.m. so we have a lot to do.

I don’t think people understand the reasons I have for staying, and I’d love to clear that up with you, starting with this viral tweet that’s going around. I never said I live on the ground floor. I live on the water, but I’m three stories up. Even with a 20-foot storm surge, I will not be seeing any of that. Second of all, I have never talked about this online, and I didn’t really intend to because it was rather traumatic. But I mentioned it in my Instagram story the other day, and now I feel very forced to go into greater detail. I mean, unless, God forbid, New York Magazine published something very snarky about why I’m not leaving. Although we know New York Magazine would never do that.

No snark here, no.
Okay. Well, Matt, you better fucking give me something to live for.

Deal.
This is all on you. I’m joking. My sense of humor is very dark, and maybe you should work that into a disclaimer. I feel like some people assume I’m very dumb in that I say everything without irony. An example that’s top of mind today — because Ziwe just texted me — is when I said I wanted an ally cookie on her show. I was like, This is my sense of humor. It’s just very glib.

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

Again, I joke. I don’t actually think she wanted me dead. She’s a very nice artist.

So why are you staying?
Okay, so my reasons for staying involve Hurricane Ian, which hit in 2022. I evacuated to my mom’s house in North Port. She lives very deep inland, but it’s very flat and I’m higher up being three stories in the air than I was at her house. It was three days, no water, no electricity, no AC, which is a huge fucking problem in Florida in late summer, even early fall. We were evacuated by boat by the U.S. military. Her whole neighborhood flooded. They drove one of those Lana Del Rey–husband fan boats down what was formerly known as her street.

The scariest part was not our dwindling food supply or the insects, which were frankly terrifying when the entire surrounding land turned even swampier than it had been in rural Florida. I hope you never find out what was actually the scariest part, which was at night we’d hear gunshots. I still don’t know if it was just drunk Floridians exercising their Second Amendment rights on 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’ve always been coming to Sarasota ever since I can remember to visit her. And as a result of that, we have a lot of family friends in the building who are very old. They’re all of my grandma’s friends that we just sort of inherited. I never would’ve been able to afford a down payment with the money I made from Scammer, even though it sold so well. The only reason I was able to finally make my first real-estate purchase was because friends and family were selling it, and we got such an amazing deal, and we’re just sort of have such deep roots in this condo building. My old friends — Ruth, Terry, Holly and her mom, Maryanne — are all staying, and someone needs to check on them.

How many floors is the condo?
It has 16 floors.

Listen, I think either one of these reasons alone wouldn’t have been enough to evacuate. I am not a first responder. I’m fucking Caroline Calloway — I don’t even want to have me around an emergency! I’m useless. So I don’t think that I am the best person to help them. But with the very scarring experience I had evacuating with Ian two years ago, the two reasons combined were definitely enough to push me. Combined with the final reason of just our building’s overall safety. It’s never flooded in all the years that my family has lived here. The windows have never shattered. I know our windows can take gusts up to 145 miles per hour. Our building also, every condo wraps around. Just because we are on the water doesn’t mean that all of your rooms face that direction. We have a lot of safe spaces that are thick concrete walls.

Did you consider the possibility that you would need to get evacuated from your condo and that it would just kind of be a sequel to that terrible Ian experience?
It is just choosing between so many terrible choices. It’s like, okay, so we get evacuated here, but then we left up all of our neighbors. And also we’ll be what in a stuck in traffic. I can’t drive. Remember, I’m a true, I spent my full last 20s either in England or in the West Village. I never got a license, so I would’ve had to wait until my mom came and got me to evacuate, which really would’ve put us behind on the traffic. So we’d be what in traffic in just a hotel that was also getting tropical. I doubt we could have made it out of the state of Florida in time, assuming that we wouldn’t have been able to leave until Tuesday morning, I think is probably the earliest she could have come and got me. So it’s just like what? We’d be somewhere else in the state in a less sturdy structure with less terrible weather, but without our neighbors, what do you choose? It’s all very difficult, and this is what I chose.

Why are your mom and two of your friends staying with you in what is essentially the heart of where the hurricane will land?
It’s really for the safety structure of this building versus where they were leaving. My mom’s in Northport in a small home, which is much more likely to have parts of it deeply damaged by debris that the wind is throwing around. I’m in a bajillion-ton concrete tank of a condo building; our roof is not going to blow off.

What’s your disaster plan? Are you boarding up windows?
We have hurricane-grade windows for up to 145 mph winds. We’ll be taping them, but we’re not boarding up. But our condo building is putting up a flood storm-surge gate, which is why we have that 7 p.m. cutoff.

But my biggest plan for the hurricane is going to be very similar to the last time there was a widespread disaster, COVID-19.

I felt then and feel now like there were a lot of qualified experts and activists with social media, large social media presences, providing incredible resources, incredible reliable resources — and that the greatest service I, Caroline Calloway, could provide in these times of high anxiety and high stress is entertainment. I think my number one purpose in this world is to make books. However, I do think a close second is performance art online and to entertain others. So my plan for the hurricane is obviously on a boots on the ground level is to stay safe, fill up the bathtub, charge chargers, etc. But I do want to try to entertain. I didn’t just commit to the bit so hard that I almost died. This was an educated decision made by an adult for a variety of reasons.

I’ve been doing interviews all morning and doing literal hurricane prep, so I haven’t given this content the thought that it deserves yet. So I wish I could tell you more about what that will be, but I do know I’m going to make something. I’m going to do what I do best, take some terrible luck and turn it into a great opportunity for content.

What about food? What else is on your prep list?
I’m going to be cooking up a lot of pasta noodles so that we have those ready to go and tapers and also frying up some dumplings. And then my mom did most of our collective shopping, but I have food for about three days, but not longer. My mom brought most of the non-perishables.

Has there been any direct contact from the county or the state checking in?
No, but Emma Roberts somehow got my phone number and wished me all the best. So I’d prefer that any day.

People have been paying attention to the story of you hunkering down. I just saw one post that reads: “Caroline Calloway refusing to leave a mandatory evacuation zone (right on the water, right where landfall is expected) and dying in a hurricane would be the perfect ending to her narrative tbh.” I was wondering what you thought about that type of thinking?
Totally agree. I think it’s a very funny joke. It’s almost, like, painfully on the nose. Like when Eve Babbitz literally set herself on fire. Although I’d like to point out that didn’t kill Eve, and this hurricane’s not going to kill me.

I really hope that you can rub this in our faces, all us worrywarts in New York.
I don’t need to rub it in your face. Just plug my fucking book.

This conversation has been edited for length and clarity.