Our First Family Trip to Disney World Was SO Good—Here's Why

By Megan Sweeney
Our First Family Trip to Disney World Was SO Good—Here's Why

Source: Megan Sweeney

Recently, I was invited by the wonderful team at Disney to visit Disney World for the first time with my family. My husband and I had been talking about bringing our four-year-old daughter for over a year, but we hesitated for lots of reasons.

Will she remember? Is it worth the cost? Is now the right time to go instead of another all-inclusive family resort somewhere else?

A Disney vacation is a bucket list item for many families, including us, so we were thrilled to be able to scope it all out to know what we would visit again if we were to come back.

The highlights of our first family trip to Disney World

Although we were only in Disney World for three days, there are so many highlights and special memories it will be hard to narrow it down to just a few.

Staying at a Disney Property Hotel

photo of the disney contemporary resort at night with the monorail going through Source: Disney Contemporary Resort

We stayed at the Disney Contemporary Resort, within a 10-minute walk of Magic Kingdom. The Contemporary falls within the top tier of resort hotels and is one of the oldest. The rooms, newly renovated with Incredibles theme, were perfect for our family.

We had a water-view room with two queen beds, a large bathroom, a small sitting area and a coffee station. A gorgeous sunrise view over the lake and the pool topped off the experience. We could even see the EPCOT fireworks at night from our balcony.


Transportation from The Contemporary to any park was easy, especially to Magic Kingdom. We could walk in less than 10 minutes or take the Disney Monorail on a short loop to the front gates. The Monorail stopped inside the hotel and quickly got us to EPCOT.

Buses are also accessible from the front of the hotel and can take you to Animal Kingdom, Hollywood Studios or Disney Springs for free.

The staff at The Contemporary was also terrific. They greeted us with open arms when we arrived and made my daughter feel so special with a My First Disney pin with her name. They ensured our Disney bands were programmed, working and fit well and helped us repeatedly find where we needed to go during our stay.

I think staying on Disney property is worth it, just for the convenience of quickly getting back and forth between our hotel and the parks. There are plenty of options for different resorts depending on what type of accommodations you are looking for and where you expect to spend most of your time.

Character Dinners and Meet and Greets

Author Megan with husband and daughter meeting Mickey Mouse Source: Megan Sweeney


My daughter is four years old and was not overly interested in the rides this time. Instead, she wanted to meet as many characters as she could. So we pre-booked a few character dining restaurants to guarantee we would meet at least a couple.

My favourite souvenir we got was an autograph and photo book at one of the shops at Magic Kingdom. By the end of the trip, it was packed with signatures. My daughter was often nervous about meeting a character or princess at first, so this was an excellent way for her to start the interaction independently until she warmed up enough to give them a hug or high five.

Disney cast members have a reputation for going above and beyond, and I can confirm from our experience that this was true. I was blown away by how special they made each kid feel and matched their energy to make them feel comfortable.

Fireworks at Magic Kingdom

view of the Disney Magic Kingdom fireworks in front of the castle at night Source: Megan Sweeney

I was not expecting to be so moved by the fireworks at Magic Kingdom. We were fortunate enough to be invited to the dessert party at Tomorrowland Terrace before the show started, including a VIP spot for the fireworks. Paying for this experience is expensive, but if you want to guarantee a great place to watch the show—it is worth the cost.


The fireworks show was unlike anything I've ever seen before. The music, the lighting, the castle, and the fireworks themselves were all so beautifully presented and moving. The combination of songs from my childhood, new characters and Tinkerbell flying through the sky at the end brought me to tears.

My daughter did find them pretty loud, so I spent most of the show covering her ears with my hands. Bring noise-canceling headphones for little ones who may have fallen asleep by the time the show starts or have trouble with loud noises.

If you're traveling with more than one child, be sure to invest in one of the best double travel strollers—there's a lot of walking and all the Disney transportation options are very stroller-friendly.

The Bibbidi Bobbidi Boutique at Magic Kingdom

Author Megan's daughter at the bippity boppity boutique with the cast member who did her hair Source: Megan Sweeney

The Bibbidi Bobbidi Boutique was not part of our plan for this trip. I showed my daughter a YouTube vlog of a family who went to the boutique, and she told me she wasn't interested in getting her hair done but just wanted the dress. I didn't look into it further and assumed finding a princess dress at Disney World would be easy. I was wrong.


Since the Bibbidi Bobbidi Boutique experience is so unique, the dresses sold there are kept for guests with reservations. You can only shop at the boutique with an appointment, and very few dresses are available at other stores throughout the park.

The more my daughter saw other little girls walking around Magic Kingdom in full princess wear and hair, the more she was determined to go herself. Luckily, we got an appointment, and I will never forget that hour with her.

Experiencing the magic together as a family for the first time

author Megan with her daughter sitting in front of the castle at magic kingdom looking at it Source: Megan Sweeney

I have a video of my daughter the first time we walked down Main Street USA in Magic Kingdom, where she shrieks in sheer joy, 'Mama! The castle!!'. I could cry thinking about it while I write this.

The magic at Disney World is unexplainable. You are immediately brought back to being a kid watching your favourite Disney movies, seeing it all come to life. The days are long and exhausting, and sleep and schedules go out the window, but wow, I would do that over and over again if we could.

So, is a family trip to Disney World worth it?


My short answer is yes. Long answer, if the Disney experience means something to you and your family and you can make it work financially, I recommend it over and over again. It is one of the most magical and memorable things we have ever experienced together as a family.

Seeing my daughter's face light up whenever she saw one of her heroes at a character dinner or meet and greet, or listening to her explain to us how everything is magic at Disney, even the elevators where Mickey announces what floor you're on, or watching her transform into an actual princess at the Bibbidi Bobbidi Boutique is something we will never forget.

We only had a little time to explore all the parts of Disney World, but it was clear there is something for everyone, and you could easily tailor the trip to any group, age or budget. If we had more time, I would've packed my best swimsuit and enjoyed the resort-style pools dotting just about every hotel property in the area.

This article was originally published on May 01, 2023

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