Over the last five years, I’ve realized that travel is a huge part of what makes me feel like me. I’ll happily say no to a lot of random or material things if it means I can say yes to experiences instead – so travel has officially become a line item in my budget. I tuck extra money into it whenever I can, because I know it’s worth it.
In 2022, I decided I wanted to start a tradition: taking one child on a big solo trip every three years. That first trip was with Lily, and we spent a magical weekend at Disney together. It was everything I hoped it would be! Fast forward to 2025, and it was James’ turn for his first big mama + James adventure!
We flew down to Florida for a weekend in Disney and stayed at the All-Star Movies Resort just before Halloween and it truly was the perfect weekend. I surprised James with matching t-shirts and told him where we were going the night before we left. From that moment on, the weekend was full of sweet, unforgettable memories with my sweet boy. Ones I’ll hold close forever. I know he had just as much fun as I did!
I’m endlessly grateful that my kids are such great travelers. It makes everything feel lighter and far less stressful. James loves flying, and watching him experience it through fresh eyes is one of my favorite things. On our flight home, we were treated to an absolutely epic lightning storm lighting up the clouds. We were completely mesmerized by it and James actually spotted it before I did!
Learning from my trip with Lily, this time around we did three park days: Magic Kingdom, Epcot, and Animal Kingdom. We even got ready for the fireworks nearly two hours early so we could snag amazing seats for the light parade and the fireworks show. During the fireworks, I definitely got a little teary-eyed. I’m so aware of what a privilege it is to travel with my children. It takes a lot of planning and effort (especially when one child is staying behind) to make something like this happen as a single mom.
This trip completely solidified my belief that staying on-site at a Disney resort and booking Mears transportation is worth every penny. No car seats. No driving. No parking. No stress. Everything is taken care of for you, which lets you focus on what actually matters: making memories!
It feels really amazing to have done this once with each of my littles now – it means the tradition is fully established and underway! What’s extra fun is that for the next trip I take with each of them, they’ll be old enough to help me plan it! If my math is correct, I’ll be able to do 3 of these big one-on-one trips with each of them before they turn 18.
So, without further ado: the financial breakdown of our weekend and the photos!
Finances
- Our flights were covered 100% by my points. We flew out of Portland and took two flights down and two flights back. If I didn’t have points it would’ve been $832.71 round trip.
- All Star Movie Resort | $1655.61 – this was for 3 nights and 3 day passes for the both of us.
- Magic Band for James | $35 (I still had mine from when I traveled with Lily)
- Parking at the airport for 4 days | $60
- Mears Connect | $60.90
- Gifts + Souvenirs | $146.77
- Food | $214.07 (this included the airport and a dinner out at the Rainforest Cafe)
- Total for the weekend out of my pocket: $2172.35
The Pictures
Linda is a Portland-based photographer specializing in weddings and creating family legacies from Portland to Boston and across New England. You can see more of her work online at lindabarryphotography.com, on Instagram, or on Facebook. If you want to reach out directly: linda@lindabarryphotography.com.
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