Is Florida safe for a trans woman on holiday?

The state’s Republican governor Ron DeSantis has waged war on the rights of minorities, so transgender woman Diana Thomas feared that Florida might prove a hostile holiday destination. But then she arrived in Key West to find the residents and hoteliers had rolled out the red carpet...

Diana Thomas went in search of a destination that would suit a solo traveller (Diana Thomas/iStock)

By the start of last November, I was absolutely shattered. It had not been a good year. I had undergone emergency spinal surgery, was diagnosed with cancer, suffered months of constant physical pain, and had watched my mother die.

At this point, I had not had a proper holiday in almost a decade and clearly, it was time I took one.

Scrabbling around the internet in search of a welcoming environment for a solo traveller with multiple health issues who was also transgender – a pretty niche market by any standards – I found a place in Key West, Florida called Alexander’s Guesthouse.

Alexander’s describes itself as: “The premier Gay Hotel of Key West. All humans are welcome!” I sent an email, explaining my circumstances, which led to an exchange of messages with a lady called Robyn, who assured me that not only would I be a more than welcome guest, I would also meet all the other residents at the daily happy hour, at which everyone gathers around the pool to chat and make friends.

I duly laid down the deposit for an eight-night stay, and sorted out all the flights I would need to get to Miami and then down to Key West, plus a two-night stay in South Beach, en route. It was only after I had already spent thousands of pounds that I questioned whether Florida would be a safe and welcoming place for a trans person to go on holiday.

The state’s Republican governor Ron DeSantis has made the culture war against minority rights a centrepiece of his administration. “We are going to remain a refuge of sanity and a citadel of normalcy,” DeSantis said in May, passing a bill that made it a criminal offence for any child to be given gender-affirming treatments and mandating schools to teach children that “a person’s sex is an immutable biological trait”. He also banned trans people from using any public toilet other than the one matching the gender on their birth certificate.

Now, I am a fully-transitioned, post-operative trans woman. My passport is marked “F” for female. I pee sitting down. But I have not obtained the Gender Recognition Certificate that would allow me to change my birth certificate, partly because I can’t be bothered, but also because I own my past life as a boy and a man as much as my current, very happy, life as a woman. I refuse to be ashamed of either identity.

Alexander’s Guesthouse welcomes ‘all humans’ (Diana Thomas)

Ron DeSantis, however, made me feel frightened, which he would doubtless consider a tremendous success. So I emailed Alexander’s Guesthouse again and had another chat, this time with a colleague of Robyn’s called Michael.

He told me: “We totally understand your concerns… [but] I am confident in saying that being/living in Key West as a member of the LGBTQIA+ community feels very different from what you may see or read in the news.

“Yes, recent changes in legislation are cause for concern and a step back in many ways. But keep in mind: you will be entering the Conch Republic. Our island community is welcoming to every body! As a matter of fact, our adopted motto is ‘One Human Family’. That’s the spirit we as locals have.”

Key West feels different to other less tolerant parts of Florida (Diana Thomas)

Suitably reassured, I got on the plane, flew off to Florida… and had an absolutely wonderful time. People were lovely to me, and I got ma’amed wherever I went. I used airport, hotel and restaurant ladies’ rooms without the slightest trouble and felt completely safe and welcome in both Miami and Key West.

On a purely touristic note, South Beach was a far cry from the somewhat crumbling, charming, Art Deco haven I remembered from the Eighties and early Nineties. But Key West was a revelation. It’s one of the few places in America where you genuinely don’t need a car. Walking shoes or a rented bike will suffice to take you up and down Duval Street where all the shopping, clubbing and action takes place, or around the quiet residential streets lined with clapboard houses, each with its shady porch from which the residents can watch the world go by.

People were lovely to me, and I got ma’amed wherever I went. I used airport, hotel and restaurant Ladies’ rooms without the slightest trouble and felt completely safe and welcome in both Miami and Key West

True, lots of the houses have the Stars and Stripes fluttering from a flagpole. But they’re just as likely to fly the rainbow flag, or that of their self-proclaimed Conch Republic. And what other US town has chickens with beautiful vivid plumage wandering along the sidewalks?

Alexander’s Guesthouse turned out to be as cosy, elegant and stylish as one would expect from a place founded 40-odd years ago by gay men, for gay men. The guests were a mix of Black, white, gay, lesbian and straight – and all were equally friendly towards me.

As for Robyn and Michael, they are my new best friends; the first hotel staff I have ever hugged as I left. But it would be unrealistic to expect everyone to be like them. So here is a summary of advice gleaned from Alexander’s guests and staff, and Elle Taylor, a transwoman who works in Aqua, one of Key West’s drag bars.

The guesthouse turned out to be cosy, elegant, stylish and welcoming (Diana Thomas)

First: stick to the liberal, tolerant areas of Florida: South Beach, Key West, Tampa, St Petersburg and Orlando, where the Disney corporation has been waging the culture war against DeSantis. But stay away from the north of the state and the “panhandle” bordering Georgia and Alabama. That’s redneck, Maga, Bible belt country.

Second: make sure all your documentation is consistent. The federal Transport Security Agency, which handles all airport security, makes a point of being gay and trans-friendly. But as Elle Taylor found, after she had legally changed her name, but had not yet acquired her legal female gender, any discrepancy between the name and gender on, say, a ticket, and that on your ID will cause trouble.

Third: this is horrible to have to say, but it’s true – the better you pass, the easier life is. In Key West, no one cares what a person wears, or does not wear. Some of the hotels are “clothing optional” and the fairy at the town’s Christmas parade was a gay man in a tutu and angel wings.

Elsewhere though, people are less tolerant of difference. If you are still at a relatively early point in your transition, you may consider presenting in your birth gender until you can be in a place where it’s safe to be who you really are.

Finally, above all, don’t let the haters win. You can be trans in Florida and still have a great time. I know, because I am and I did.