Answered by a travel agent, mom to three boys, and Disney nerd who’s been going to the parks since she was a toddler.
Planning your first trip to Disney World can feel overwhelming especially if you’re not working with a travel advisor. Maybe you’re unsure if your family is even ready for Disney yet. Today I’m diving deeper into the most frequently asked questions I get from clients planning their first family vacations to Disney World.
I’ve been going to the parks since I was a toddler. We took yearly family vacations to Disneyland while visiting family in California. Once I had my first kid, taking our own family to Disney was always on my mind. Now that we live on the East Coast, Disney World is much more convenient and once we finally went, we fell in love.
Watching your child’s face light up as they meet a favorite character, see a parade, or stay up late for fireworks after a long but magical day there’s nothing quite like it. Helping other families create those memories is one of my favorite parts of the job.
Question 1: Help! Where do I even start?
Start with when you want to go. Every family is different, so choose a time that works with your school or work schedule. If you have a flexible calendar, these are my top picks (each with pros and cons):
- Late January / Early February: Cooler weather and used to have lower crowds, but crowds have increased in recent years. The downside is many major attractions may be closed for refurbishment.
- Early September (right after Labor Day): Crowd levels drop significantly, but it’s still very hot and humid and it’s peak hurricane season.
Question 2: Should I stay on or off site?
Many assume Disney resorts are more expensive, but they often don’t factor in everything that’s included. Disney also runs promotions that can make on-site stays surprisingly affordable.
Best value: Disney’s value resorts (All-Star Music, Sports, Movies, Pop Century, Art of Animation)
Off-site only makes sense when splitting costs with a larger group
If you stay off-site, be sure to factor in:
- Parking fees (both hotel and theme park)
- Resort fees
- Lack of included transportation
Disney Resort Perks: free resort + theme park parking, free transportation (bus, monorail, Skyliner), 7 day lead time on lightning lane selections, and a current 2026 promotion: free kids dining plan with a paid adult dining plan.
Question 3: How many park days do we need?
I recommend at least one day per park, and ideally two days for Magic Kingdom plus a rest day or two.
Avoid park hopping on your first trip – it’s time-consuming and overwhelming. Stick to one park per day to keep things simple.
Question 4: What are Lightning Lanes and do I need them?
Lightning Lanes = Disney’s system to skip the standby line.
Three types:
- Single Pass: Pay per person for one top-tier ride (e.g. Tron, Mine Train, Guardians, Flight of Passage, Rise of the Resistance) (can purchase 2 per day)
- Multipass: Pre-select 3 rides and access most others via Lightning Lane
- Book 7 days ahead if on-site, 3 days ahead if off-site
- Book additional rides throughout the day after scanning into your first
- Book 7 days ahead if on-site, 3 days ahead if off-site
- Premier Pass: High price, access Lightning Lanes for every ride in one park with no need to book ahead of time or be booking during the park day
Yes, it’s complicated, but I always recommend Lightning Lane access, especially for families with young kids. It saves hours in line.
Grab my list of recommended Lightning Lane Multi Pass Selections here:
Question 5: Is the dining plan worth it?
Only if you want the all-inclusive feel. Most families don’t save money unless they plan and calculate carefully.
Exception: Bookings for 2026 include free kids’ dining plans when you purchase an adult dining plan. This can lead to huge savings if you’re planning to eat in the parks.
Question 6: Can I bring my own food and stroller?
Absolutely! Disney is very lenient about bringing your own food. Just follow their rules about coolers and ice.
Strollers are allowed, but no wagons, and there are size restrictions. I recommend bringing a stroller for kids up to age 9. It’s a lot of walking!
Question 7: What’s the best park for toddlers? Can they ride everything?
Magic Kingdom is hands-down best for toddlers. It has the most family rides, many with no height requirement.
EPCOT is my second favorite for little ones.
Also don’t forget:
- Character meet & greets
- Parades
- Shows
- Play areas and playgrounds
Grab my list of no-height-requirement rides here:
Question 8: How can I save money or do Disney on a budget?
Disney is expensive, but you can save by:
- Visiting in January or September (historically lowest ticket prices)
- Watching for hotel or dining promotions
- Bringing snacks/food
- Buying souvenirs ahead of time
- Using discounted gift cards
- Setting a budget for food and extras
- Booking with a travel agent
I’m always watching for discounts I can apply to client bookings.
Question 9: Should I use a travel agent? Are they really free?
YES and YES!
As a travel agent, I tailor the trip to your family’s needs and handle all the details including dining reservations, Lightning Lanes, itineraries, and strategy.
And you don’t pay anything extra, Disney pays my commission, so if you book directly, you’re missing out on expert help you’re already paying for.
If you made it to the end, thanks for reading! Drop your questions in the comments, or click here to fill out my free quote form and start planning today. 🌟
Nicki M Travel 
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