I had learned a lot about planning a Disney trip from taking Tomatico on his trip when he turned 8. When my youngest turned 8 he was ready to go and I was back at it planning an even bigger and better trip!
Disney with my Youngest
At the time of his trip, Tomatico was a bit anxious about going on some of the more thrilling rides. I couldn’t convince him to go on some of them. My youngest didn’t share any of those reservations. He’s a thrill seeker and he wanted to go on all the rides if only to show up his big brother.
Using Touring Plans again and booking a trip just before Labor Day again in 2019, we hoped to have reduced crowds and prices like we did on Tomatico’s trip.
Tomatico and I had had a fantastic time at PopCentury as it was a great value, but we also wanted to take advantage of a benefit of my Citi Prestige card (no longer available) for this trip. The benefit allowed the 4th night free on hotel stays. At the time I could book the benefit through a concierge and get specific rates, like a AAA rate. In its current form the card still offers a 4th night free, but you don’t have access to the same types of rates and the rates are usually higher, negating the value of the 4th night in many cases. Luckily I was able to use the full benefit by booking before the change went into effect on the card so this stay.
We decided to stay 8 nights total but we’d have to switch hotels in order to get 2 nights free. We ended up booking 4 nights at the All-Star Sports hotel for $109/night. This time I booked a preferred room rate rather than the absolute cheapest rate because the cheap rooms were a LOOOONG ways from the lobby where the food court and transportation was located. It was worth the extra few dollars. I booked the second 4 nights at Pop Century, also in a preferred room for $139/night. In the end I’d be getting almost $250 back via the 4th nights free and was still paying very reasonable rates for the rooms.
For tickets we went back to Undercover Tourist to get a 9 day Park Hopper PLUS pass. This allowed us to visit multiple parks in a day like I had with Tomatico. The PLUS part also allowed us into the water parks or play mini golf or some of the other activities. We got nine of these “Plus” activities each to use over the nine days of our tickets. We could use multiple per day if we wanted (ie go to a water park and then play mini golf before going to a park in the evening).
We did the same strategy with flights at with Tomatico getting an early flight on arrival day and an afternoon flight on departure day. We were able to snag some Delta seats using points on the way down and JetBlue for our return. Interestingly I booked an aisle and a window for our Delta flight down, not booking the middle. When we took our flight, I believe that is what snagged us an upgrade to first class! They probably wanted our entire row for a family and it was easiest to upgrade the two of us (most groups were probably larger than 2 people). We enjoyed the extra legroom but the rest of the first class service was lost on both of us.
While we had signed up for the Magical Express bus to take us from the airport to our hotel, when Tomatico and I had taken it we had been stuck waiting for the bus seemingly forever. I decided we’d just take a Lyft to the hotel to get our day started sooner. We did end up taking the bus back to the airport at the end of our stay.
During our days at the parks, I had also learned from Tomatico’s trip that it was easiest to take the Disney bus into the parks in the morning, but at closing time, taking a Lyft back to the hotel saved valuable amounts of time and stress. Waiting in lines for the bus at the park at closing time could take an hour or more. I was happy to spend the $10 on the Lyft (including a nice tip!) to gain an extra hour of sleep. In fact used Lyfts much more frequently during this trip.
Comparing Trips
Each trip was different and both were fantastic in their own ways. It was amazing being able to spend quality focused time with the boys one on one. It was great bonding time. I let them take the lead on choosing activities and rides. The plans we made using the Touring Plans app helped guide us, but they did not dictate our days and we improvised quite a bit. They were most useful for planning the first few rides of the day and to help us prioritize what we wanted to see and do.
We also found that we wanted to be there at opening time (rope drop) to get as much done before 1pm. We’d often go back to the hotel to relax and cool down before heading back after dinner to take advantage of the cooler temperatures and thinner crowds.
We got a lot of counter service food so it never felt overwhelmingly expensive. We ate a lot of kids meals which are generous in size and not terribly overpriced. The strawberry smoothies from Joffrey’s were our guilty pleasure that we limited ourselves to one per day.
Being just the two of us and both wanting to be there made things so much eaiser. If he was getting tired/cranky, we just went back to the hotel. If they wanted to do more, we did more. There wasn’t a third (or fourth) person to negotiate or compromise with. We were much more relaxed than many of the families we saw in the park.
So I guess my number one piece of advice for family going to Disney is to SPLIT UP. If you have two kids and two adults, each take one. Make soft plans to catch up around lunch somewhere, but don’t be afraid to cancel them. Switch kids on different day if you want. Swap kids at noon, or whatever, just take your cues from the kids. If you can do what we did and take only one kid at a time, that could be even better!
My wife doesn’t “do” Disney so it would have been a constant adjustment and compromise. The boys would want to do different things at different times. It would have been miserable if we had all gone together for their first time and we all couldn’t be happier how it worked out by going separately.
Tomatico Travels 
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