Today we’d like to introduce you to Oviedo Santa Andrew (Andrew Cheshire).
Hi Oviedo Santa Andrew, thanks for sharing your story with us. To start, maybe you can tell our readers some of your backstory.
As a boy, Christmas was always my favorite time of year. I loved the decorations, the lights, and the happiness that seemed to fill the air. My family has always embraced the holiday spirit, and when we moved to Oviedo, we began hosting an annual Christmas party for family, friends, and neighbors. To add a little extra magic, I rented a professional Santa suit for the first time, and that’s where the magic began.
Each year, when I transformed into Santa, I was amazed at how well the transformation resonated with others — even my long-time friends were shocked at how closely I embodied the character. But what really made it special were the reactions of the children. Their eyes lighting up and seeing joy spark in the hearts of people of all ages became something I wanted to share with more families. It was in those moments that the idea of ‘Santa Andrew’ began to take shape.
I decided to invest in my own suit and officially embark on this journey to bring joy and magic to others. It was also around this time that I launched Cheshire Collages, where we offer customized Santa photo shoots. Unlike the typical mall experience, I’m able to create a personalized, one-on-one interaction with each family. Before the shoot, we send out individualized questionnaires to make sure the experience feels special and magical. We want our guests to leave with a smile on their face and joy in their hearts.
Our street, Neely Street, is always beautifully decorated, which draws families from all over Central Florida. We start decorating our home in early November which really helps me get into the holiday spirit. In addition to my personal appearances, I’m fortunate to donate my time to charities. Last season, I volunteered at a holiday event at Stenstrom Elementary and worked with HopeHelps. I also make appearances at corporate Christmas events, private parties, and I love passing out gifts, taking pictures, and chatting with guests.
I’m truly grateful for the opportunity to portray one of the world’s most beloved characters. It’s such a joy to create lasting memories, and I’m excited to continue doing this for many years to come.
Alright, so let’s dig a little deeper into the story – has it been an easy path overall and if not, what were the challenges you’ve had to overcome?
One of the biggest challenges of being Santa is having to think on your feet when children ask unexpected or challenging questions. This year, for example, I encountered a few questions about Krampus, like whether I know his mother. These questions often come from what kids are seeing or hearing in movies or stories, like the recent “Red One” film.
It really made me realize how important it is to stay tuned into current culture and media, because kids pick up on all kinds of things that might seem surprising for Santa to address. The real challenge is figuring out how to respond in a way that respects the child’s curiosity while protecting their innocence and sense of wonder. It requires a balance of honesty, creativity, and sensitivity—answering thoughtfully so the child feels heard, but also keeping the magic and joy alive in their heart.
Thanks for sharing that. So, maybe next you can tell us a bit more about your work?
I’ve worked in the HVAC industry for over 15 years, currently as a Service Sales Representative at Johnson Controls. I started out as a helper/apprentice for five years and worked my way up-which I am proud of.
Over the years, I’ve developed a strong ability to read people and think quickly on my feet, which has proven invaluable — even when handling challenging questions from customers or, believe it or not, children! I genuinely love connecting with people, and that passion really shines during the holiday season when I’m especially focused on building rapport and creating positive experiences.
I am highly extroverted and thrive in fast-paced social environments, which helps me excel in sales roles that require both energy and empathy. I believe my combination of technical knowledge and interpersonal skills allows me to deliver great service while building lasting relationships.
My philosophy that everyone should be given a chance and have someone listen to them regardless of age or status is how I live my life. This sets me apart from others because just simply listening and caring, can make someone feel validated and respected-completely changing around one person’s day or outlook and that means the world to me.
Where do you see things going in the next 5-10 years?
I feel there will always be a need or want for Santa. The physical Santa experience in my eyes cannot be replaced by AI, as many things are starting to be. I have received requests for online meetings with children from out of state and I do see that continuing in the future-especially as children are more and more involved with technology. This year we are hoping to reach more children with a “Santa Andrew Story time” on Youtube starting in late November.
Pricing:
- Corporate Events-$175 an hour
- 30 Minute House Visit-$100 (within the Oviedo area, outside of Oviedo please inquire for travel rates)
- Xmas Eve House Visit-$200 for 30 minutes
- Select Dates coming soon for winter photo shoots with Santa/$75 for 15 minutes and 10 digital images
Contact Info:
- Website: https://www.oviedosantaandrew.com
- Facebook: https://www.facebook.com/santa.andrew.2025
Image Credits
Cheshire Collages
