A holiday in Blackpool helped me come out as trans

I had butterflies in my stomach and my mouth was dry as I nervously reached for the door of the cocktail bar.

Taking a deep breath, I put on my best smile and pushed it open to reveal over 30 women laughing, drinks in hand, all happily chatting and getting to know each other.

I smiled like a Cheshire cat and I knew it was going to be an amazing week – after 13 long months of planning a holiday specifically for transgender women and crossdressers (the latter can be the start of transitioning for some people).

Since I was a teenager, I’ve always known I wasn’t happy with my gender. I hid it, but after more than a quarter of a century in the closet, the need was too great to simply continue as I was.

The first time I felt brave enough to step out into public as my true self – Lindzy – was about 15 years ago at the age of 41 when I checked into a hotel in Blackpool.

It was a four-hour drive away, but I’d seen a lot of posts on social media about the LGBTQ+ bars there and how safe it was.

It took me three hours just to work up the courage to leave my room in my red jacket and long skirt, as nerves and anxiety raced through me.

I took a short walk to a local LGBTQ+ bar and was greeted with looks and stares. ‘Is it me?’ I wondered. ‘Do I look like a man in a frock?’

I was petrified. Then just as I was about to turn around and walk back to my hotel, a stranger said: ‘Hi gorgeous, the bar’s that way’, with a knowing grin. I will never forget that – a few simple words meant the world to me.

I felt safe at the bar. Lots of other girls came and said hello or asked me to join them but I was too shy so I just observed all evening. 

At the start of my journey, I felt alone, scared and very vulnerable.

I’d grab the odd moment to dress up, experiment with make-up and secretly buy clothes online. But the yearning to do more became stronger and stronger, to the point where all I could think of was the next opportunity to be myself.

I had just started dating my current partner, Gabby, in 2007 but she knew nothing about Lindzy. Over time, she started to get an inkling and would carefully ask me questions like, ‘what should I wear with this skirt?’ Or she’d see how I reacted to her playfully trying to put make-up on me.

Until one day she just asked me outright. I had dreaded this moment but knew I had to tell her. She just smiled and said, ‘Come on then, show me Lindzy’.

Since that day, she has been by my side. It’s not always been easy, but Gabby has helped me become comfortable with who I am today.

Over the years, I’ve been away for long weekends in the UK by myself or with Gabby and I always get anxious just walking down the street, especially in a place I haven’t been before.

Once in Bournemouth, a child looked at me and asked her mother, ‘Is that a man or a woman?’ It still hurts and it’s something I’ll always remember. 

As a result, I was very aware that our community needed a holiday location where both out and closeted trans people or crossdressers could relax, grow in self-confidence and get support and guidance from each other in a safe environment.

That’s when I had a lightbulb moment in September 2022 for ‘Trans Holiday’, which is a trans-exclusive week-long stay in a UK-based resort.

The event was desperately needed to help those of us who were lonely, had dysphoria or were petrified of stepping out of their front door. We all need a safe place to be ourselves, or to make new friends to talk to, dance and have fun together without harassment or humiliation.

So I hit the ground running and found a venue in Mill Rythe on Hayling Island in Hampshire in November of that same year. The hardest part was advertising, event planning, promotion, social media and website-building because it was all new to me.

It didn’t help that there were no reviews, just my pictures and promises. How would I build confidence in this inaugural event within the community? 

Every day, I was posting the event in various groups on Facebook and, slowly but surely, bookings began rolling in. By September of last year, we had all the available 58 caravans booked, which was around 100 guests.

That’s when the nerves properly kicked in.

But I needn’t have worried because the event itself in November was better than I could ever have imagined. I had visualised so many aspects of it in detail but watching it come to life was very emotional and, to be honest, unexpected.

After I walked into the cocktail bar on that first night, I had arranged for a live singer to perform and the venue was packed – all I could hear was laughter and joy.

What an emotional evening that was, not just for me but the joy and elation from so many.

When I looked around the room that night, there were people of all ages. From women in their 20s, all the way up to a lovely couple from the Isle of Wight – both in their 80s and married for 60 years, but one of them on their first time ‘out’ as a girl.

That night, as I headed back to our caravan for the week with Gabby – who had been by my side the whole journey, a total pillar of strength – she said, ‘Well that went well didn’t it,’ with a cheeky grin on her face.

And it was only the beginning.

During the week, I witnessed so many examples of new friendships being developed. Everyone I spoke to – the women and their partners – commented on how amazing it was just to be able to talk openly to like-minded others.

There were women experiencing things for the first time, such as ordering a drink. I could see one shaking at the bar with fear, so I simply stood next to her and smiled, just to let her know it’s OK. For others, it was a thrill just to leave their nail varnish on all week.

Some had their make-up done by a professional make-up artist for the very first time, while others were even able to go swimming in a bikini – myself included. Changing into my new swimsuit and that feeling of freedom was unexplainable.

There was a full programme for the week, including cocktail-making competitions, themed nights (school disco and back to the 80s), quizzes, movie matinees, makeover tutorials, live singers, and an amazing magician, Bill.

There were so many stories of individual achievement, so many tears of joy. Some people even cried as they checked out after the week, with one in particular remarking to me, ‘This holiday has changed my life.’

The positive response we got from everyone while watching people’s self-confidence grow was overwhelming.

As a result, I am very pleased to say that ‘Trans Holiday’ for 2024 was fully booked within a week, with over 160 guests now attending in October 2024 at Mill Rythe again.

It will be bigger and better, with more entertainment. We are even looking at an additional mid-year holiday in April 2025, giving us two each year. 

When I look back at my early years – especially how vulnerable and lonely I felt – to now, I feel so overwhelmed and amazed how far I have come. Organising a successful holiday was a major step for me. Sure, it was daunting at times, but I got there.

I set out to encourage all those who are too scared to simply walk out their front door to realise their dreams. Achieving that is the greatest feeling in the world.

Find out more about Trans Holiday on their website here.

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