A Multi-Generational Walt Disney World Resort Trip (With a Baby!)
Written By: Senior Travel Advisor, Payton Rudolph
Traveling to Walt Disney World with three generations, multiple strollers, and kids ranging from 6 months to 4 years old was no small feat — but with the right planning, it turned into a really special (and very doable) family vacation. Here’s an honest recap of our January 10–15, 2026 trip, from a travel advisor who specializes in family vacations and lived it firsthand.
The Group & The Timing
Our crew included me, my husband Cooper, and our 6-month-old daughter, Georgia, plus my parents and my sister’s family with a 4-year-old and 2-year-old. January was a great choice: mild weather, manageable crowds, and perfect pool temperatures for little ones who don’t last long in the parks.
Resort Stay: Disney’s Caribbean Beach Resort
We booked Caribbean Beach for its central location and Skyliner access, which ended up being a huge win for a multi-gen group.
I stayed in a Preferred room in Barbados (first floor, as requested). The room was clean and comfortable, though it’s definitely due for a refresh. The location, however, was very convenient for both Old Port Royale and the Skyliner.
My parents and sister’s family had Standard rooms in Trinidad, and their rooms were noticeably more updated with cuter theming. However, these are further away from the Centertown or main area of the resort. It was a great reminder that not all “Standard” rooms are equal — something I’ll be very selective about with future clients.
Housekeeping was every other day, as expected for a moderate resort, and they were quick to bring a crib for Georgia when requested.
Resort Amenities & Transportation
We only used the pool and splash pad on check-in day, but the weather was perfect and the kids loved it. Mobile ordering became our best friend for quick meals and coffee.
Transportation-wise, the Skyliner was the MVP. It made EPCOT days and Riviera visits incredibly easy — and my 4-year-old niece declared it her favorite ride of the entire trip. Buses worked fine for the other parks, but multiple stops and folding strollers can slow things down, especially with little kids.
Park Touring Strategy
We did 3-day, one-park-per-day tickets with a rest day:
Animal Kingdom (Sunday)
EPCOT (Monday)
Resort Day (Tuesday)
Magic Kingdom (Wednesday)
We purchased Lightning Lane Multi Pass for each park day and Single Passes for all eligible attractions. Honestly, with kids, I wouldn’t do Disney without Lightning Lanes — it keeps everyone happier and avoids unnecessary meltdowns.
Animal Kingdom was a slower start with no rope drop, while EPCOT and Magic Kingdom were rope-drop days with a focus on staying in one land at a time. EPCOT was especially easy, and taking a midday break via the Skyliner was a game-changer.
We skipped fireworks as it was too late for our littles but we loved the Starlight Parade at Magic Kingdom. Sitting closer to the park entrance made for an easy exit — something I always recommend for families with young kids.
Dining (With the Disney Dining Plan)
We all had the Disney Dining Plan, and for our family, it was absolutely worth it — especially since we maximized value with drinks at eligible meals.
Highlights included:
Yak & Yeti: Excellent food and drinks, we shut down the park and the restaurant with this one!
Akershus (Breakfast): A fantastic value with five princesses and a quick, kid-friendly meal served family style.
San Angel Inn: Beautiful atmosphere and great food. The margaritas are excellent!
Topolino’s Terrace: Adorable characters and a hit with the rest of the family. Spend some time on the terrace afterwards for breathtaking views of Disney World.
‘Ohana Breakfast: Fun characters and delicious array of food - plus tasty Hawaiian bread upon entering the restaurant!
Final Takeaways (From a Travel Advisor)
Caribbean Beach is a great fit for families with a moderate budget who care about location and transportation. As this is a huge resort, I’ll be very intentional about explaining the resort’s different sections and setting expectations around room requests when working with families.
Overall, this trip was proof that Disney can work beautifully for multi-generational families — with the right resort, pacing, and planning. And yes, even with a baby!
Contact Payton today at Payton@BeOurGuestTravelCompany.com