When people start planning a Disneyland vacation, one of the first questions that usually comes up is: “Should we stay on Disneyland property, or should we choose one of the nearby Good Neighbor hotels?” And honestly, it is a great question. Disneyland is very different from Walt Disney World in this way. At Walt Disney World, staying on property often feels like the obvious choice because of the size of the destination, the transportation system, and the overall resort layout. Disneyland, on the other hand, has many nearby hotel options within walking distance of the parks, which can make the decision feel a little less clear.

Planning your first Walt Disney World vacation is exciting — but it can also feel completely overwhelming. Between the resorts, dining reservations, Lightning Lane, park tickets, transportation, stroller decisions, early mornings, late nights, and all the opinions online, it is very easy to feel like you are already behind before you even start. Even as someone who now helps families plan Disney vacations every day, there are things I wish I had understood better before planning my own trips. Things that would have saved stress, helped me set better expectations, and made the trip feel a lot more magical. So if I were planning my first Walt Disney World trip all over again, these are the ten things I wish someone had told me.

Solo parent travel has such a special place in my heart. And when I say solo parent travel, I mean that in every version it can come in. Maybe you are a single parent. Maybe your spouse cannot take time off work. Maybe you are divorced or co-parenting. Maybe you are widowed. Maybe you just really want to take your child on a special trip and you are the adult who is making it happen. Whatever the reason, I want you to know this first: I love it. I support it. And I do not think you should have to talk yourself out of it just because it feels intimidating. Traveling as the only adult with your child or children can feel like a lot. You are the planner, the packer, the navigator, the snack holder, the bathroom finder, the meltdown manager, the memory maker, and the person who has to keep everyone’s documents, tickets, meals, sunscreen, and sanity in order. That is not a small thing. But it can also be one of the most rewarding ways to travel. There is something really beautiful about getting that one-on-one time with your kids. No splitting attention. No group voting. No trying to make the trip work for ten different opinions. Just you, your child, and the chance to make memories that feel completely your own.

Disney’s Caribbean Beach Resort is such an incredible asset to the moderate resort category at Walt Disney World. It has so much going for it, especially for families who want more than just a place to sleep at the end of the day. Between the relaxed island atmosphere, great dining, fun pool area, Skyliner access, and rooms that can sleep up to five, Caribbean Beach can be a really strong fit for the right family. But — and this is a big but — this is also a resort where the layout matters. A lot. Caribbean Beach is large. Very large. It is spread out across multiple villages, with several buildings within each section. Depending on where your room is located, getting to dining, transportation, the pool, or even your morning coffee can require some extra walking. For some families, that feels peaceful and resort-like. For others, especially after a long park day with tired kids and a stroller, it can feel like a lot. So let’s talk about who this resort is amazing for, and who may want to think twice.

Disney’s Caribbean Beach Resort is such an incredible asset to the moderate resort category at Walt Disney World. It has so much going for it, especially for families who want more than just a place to sleep at the end of the day. Between the relaxed island atmosphere, great dining, fun pool area, Skyliner access, and rooms that can sleep up to five, Caribbean Beach can be a really strong fit for the right family. But — and this is a big but — this is also a resort where the layout matters. A lot.

Group trips sound like a dream… until you’re the one trying to plan them.

More often than not, they don’t fall apart because of the destination. They fall apart because of the planning.

If you’ve ever felt like you’re doing Disney wrong… you’re not alone.

Somewhere along the way, planning a Disney vacation stopped being about your family and started being about doing it “right.” Social media is full of tips, hacks, must-dos, and perfectly curated itineraries that make it feel like if you’re not doing everything, you’re doing it wrong.

But here’s the truth: that pressure is one of the biggest reasons families come home from Disney feeling exhausted instead of fulfilled.

Let’s talk about one of the biggest misconceptions in cruising right now.

“Virgin Voyages is just a party cruise.”

I hear this all the time—and I get it. The branding is bold. The vibe feels modern and a little edgy. Social media tends to highlight the nightlife, the energy, the fun.

One of the most exciting parts of planning a Disney Cruise Line vacation is choosing the right stateroom. While every cabin onboard Disney ships is thoughtfully designed with families in mind, the type of stateroom selected can really shape the overall cruise experience.

For many families, the idea of a Disney vacation feels equal parts exciting and overwhelming — especially when sensory needs, big emotions, or neurodivergence are part of everyday life. As both a parent and a travel advisor specializing in Disney vacations, I want you to know this first: You don’t need a “perfect” plan to have a magical trip. You need a supportive one.