Disney with Lily

The Why

Not long before Steven and I separated, I read my grandfather’s story. It’s a huge binder that my Gram created (one for herself and one for him) that went over his life story. In that binder I read about how they would travel together as a family all across the country when my dad was growing up. My dad is one of five. And all I could think was “if they could make it work, we could make it work.” I was incredibly inspired by that. I have fond memories of traveling a lot as a kid myself with my family (and I’m one of four!), and I wanted to create that for my family as well. Again, if my parents could do it, then we could too!

After we separated, I decided right then and there that I wasn’t going to let single parenthood define me, and what my family’s memories would be. I decided I would take Lily and James on family trips every single year, just like my parents did, and big one-on-one trips with each of them. Did I know how this was going to work? Not at all. But we always make things that matter to us a priority. And this matters to me.

In June of 2021, I decided I was going to take Lily to Disney on a very short trip, at the start of my April break, because my school went on vacation a couple days earlier than other schools. It seemed like the perfect time!

This trip was so so special. I waited until the day before we left to tell her about it! The closer we got, the harder it was to keep it a surprise! There are so many sweet memories that I have from this trip that I’ll never forget. I’ve stored them in a note on my phone, and I plan to write them down in Lily’s journal soon. There were several times where Lily was so brave – especially when we got caught in an intense thunder and lightning storm, while fireworks were going off (all of Lily’s least favorite and most terrifying things). She was so excited about every step of the trip, and she was such a trooper staying out all day! We took a break on Animal Kingdom day and took a nap, but she did so good!

I absolutely loved being able to see everything through her eyes. It was all so sweet and innocent 🙂 Even though we only had one day in each park, I really felt like we did SO much, and like there wasn’t much else that we felt like we wanted to squeeze in after the fact!

It took a lot of planning and saving to make this happen, but it was worth all of it! I can’t wait to do this again in three years with James. That’s the rotation I’ve decided on, every three years I’ll do a big adventure with one child (along with our regular local one-on-one dates), and each year we are going to travel somewhere in the US together for a family trip 🙂 I’m so excited to make so many memories of travel with Lily and James!

My advice

Book a Disney resort. I know it probably costs a little bit more, but I wanted this trip to be the least stressful it could be, and I know that the reason it wasn’t stressful was because I stayed at a resort. Bringing a car seat wasn’t necessary. I didn’t have to worry about driving, or parking half a mile from the park entrance, or figuring out lodging near by. By staying at the resort, I was able to take a shuttle from the airport to the resort; take shuttles that were super easily accessible and regular from the resort to the hotel; I could use my MagicBand for literally everything; and Lily was obsessed with how cool our character resort was! It truly was magical!

The one thing I’d do differently is book a third day at a park. I was worried that if I did that, we’d only have a half day there because of travel plans, and that it wouldn’t be worth the money. I was wrong. After seeing how much the two of us fit in during each day, we could’ve been very happy with another half day in either park! But also, Lily was just as stoked to walk around Disney Springs and sleep in on our last day there! I also tried to buy tickets last minute, but they were booked out for another week or so, so I wasn’t able to do that, which is okay!

There’s also an app now for Disney and it really is the coolest and so helpful! If you’re staying at the resort it’ll update the times the buses are leaving; show you your charges made with the Magic Band; it shows you all the wait times for the rides, as well as how to get to each location. It really was such a cool and beneficial app!


Prior to the trip //

  • Disney Resort Hotel Package: $1405.97 // This included 3 nights at the All Star Movie Resort; theme park tickets for both Lily and I – one day at Magic Kingdom, one day at Animal Kingdom
  • Flights: $878.80 (I used $548.06 in points, so I paid $330.73 out of pocket for our flights)
  • Day before the trip: $35 upgrade to priority to booking for our flights to Disney (which I’m glad we did because Philly was an s-show)
  • Custom matching t-shirts for Lily and I: $50
  • Mears transportation (to and from the airport): $60 for both ways

During the trip//

Day One: (travel to disney)

  • $15 on food in the aiport

Day two (Magic Kingdom):

  • $13 breakfast at the hotel
  • $22 snack
  • $23 lunch
  • $6 ice cream
  • $77 dinner at The Crystal Palace (including the tip)
  • $97 gift shop (we used $80 in gift cards)

Day three (Animal Kingdom):

  • $13 breakfast at the hotel
  • $30 lightning lane (ended up being a waste, because I messed up how to use it, haha)
  • $12 ice cream for Lily and I
  • $37 stuffed animal cub for Lily
  • $12 lunch/snack at the hotel
  • $13 gift shop
  • $60 dinner at the Rainforest Cafe (including the tip) which we LOVED
  • $55 gift shop
  • $5 photo booth

Day four (Disney Springs + travel back home)

  • $16 breakfast
  • $91 caricature
  • $30 pizza lunch (sooo good!)
  • $16 M+M store
  • $17 airport snack
  • $8 airport snack

Total Spending for everything Disney trip related for Lily and I: $2469.70.

Obviously a trip like this will cost more for larger families. I used You Need A Budget back in June and created a savings target for the trip. This allowed me to see exactly what I needed to set aside each month to cover all the expenses and save up for spending money! I set a budget for $550, along with the $100 in gift cards I knew I had, and that ended up being just right for the two of us. I knew that I didn’t want to have to say “no” to every single thing Lily asked for (I definitely didn’t say yes to everything either haha) because of having too tight of a budget. Much to my surprise, she wasn’t really into the shopping part all that much, and that was fiiiiine by me!

Ways to save money:

Find a credit card (as long as you’re in a place financially to responsibly use one!) that has a good sign on bonus, like if you spend X dollars in 3 months, you get X number of bonus points. These points can be so helpful when trying to buy flights! I was able to pay for over half of our flights just from using points available on my business credit card.

Resorts. I know they’re expensive up front, but the fact that it rolls in transportation too is so huge for spending. I didn’t have to spend money on gas, or extra time walking to the parks, or stressing over directions and parking. And the fact that I wasn’t paying for flights, a hotel AND a car, is pretty big!

Bring snacks into the parks with you. The food is expensive (though, when you think about how massive Disney is and what their upkeep must be as well as paying all of their employees – which, by the way, I didn’t encounter a single rude employee there – everything is probably actually really reasonably priced, haha), and having snacks to help hold you over can help cut down on food costs! Lily and I mostly just snacked throughout the day and then had a good dinner in the evening and that was enough for us!

For holidays or birthdays, ask for Disney gift cards! They can be used *anywhere* in the park, and can help you reach your savings goals!

I used my actual camera rarely during the trip, and used my phone most of the time. That worked out just fine for me, and I asked the park employees who did the photo pass to take a photo with my big camera after they took one with theirs! I love these few photos we have together. They mean everything 🙂

I’m not an expert by any means, but I wanted to share details of exactly how much we paid for everything, in hopes that it’ll be helpful to someone!

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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You can usually find me adding books to my never-ending “to read” list; challenging myself to do things like not shop for a year; sneaking crispy m+ms from my secret hiding spot so I don’t have to share them with my daughter; and melting over seeing my children smiling at each other.

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