Grumpy Old Men on Tour: Walt Disney World

NOTE: The events in this post and the following series all took place pre-COVID. Many of the rules and planning for a trip to Walt Disney World (WDW)have changed since my last trip. Be sure to do your own research as things change frequently right now at WDW and any destination in general.


“Do you want to go to Disney World?” my friend Bob casually asked.

“Always, you know that,” I replied.

“No, I’m serious. I think that I’ve waited long enough and I’m ready to give Disney a try,” he said.

Did I hear that right? Has Bob finally given in? Is he ready after all these years to head down to the land of the mouse? I looked across the table at him. He seemed sincere. But Bob is a good actor. I looked at his face carefully for any signs of deception. No, I really think he means it.

Just to give you a little background, Bob and I have been friends nearly our entire lives having first met in the fifth grade (he says it was the fourth). We grew up together, participate in the same activities – mostly community theatre – enjoy Star Trek, Star Wars, anything with “star” in the name really, comic books, and pretty much everything geek. If we diverged in our geekness at any level it was that I was a Disney kid and he was, I thought, indifferent. I’m also DC and he’s Marvel, but that’s not the point of this story. However with every trip I took to Walt Disney World one thought often popped into my head, Bob would enjoy a trip here. Finally, deep into our middle age, the time had arrived.

“I just think that what with the new Star Wars land opening and all that I’d really like to go,” he continued, “You’ve been several times so I can’t think of anyone else I’d rather go with. So, do you want to go to Walt Disney World?” he repeated.

“Absolutely. When do we leave?” I said as I did a little happy dance in my head.

The Planning

Planning a trip to Walt Disney World is like planning an expedition into the back country. The more you know before you go and the more you’ve planned the trip out the better your results will be. It’s not something most of us can do spur of the moment for a couple reasons.

We set a date several months out, nearly a year if I recall correctly, and decided on February 2020. Bob took to researching the hotels, attractions, food, shows, everything we could think of. My mantra during this process was “it’s Bob’s trip, I’m just along for the ride.” I have had the good fortune of being able to visit both WDW and Disneyland many times over the past 40 years or so starting with a family vacation to WDW and Florida in 1975 (pictures from that epic vacation below). So I enjoyed watching Bob digging in to find out as much as possible about the “world” before we left. I was more excited that I thought I might be – I may be a veteran but I’m not jaded – and it had been about 20 years since my last dedicated trip to WDW. I had been mostly tacking on a day or two at the resort to various business trips and other visits to Florida and a few trips to Disneyland since then.

It has never been easier to research going anywhere today, but especially to WDW. Not only is there the official Walt Disney World website but there are a variety of “fan” sites and blogs that can tell you almost anything, and almost too much, about every aspect of WDW. A couple of my favorites are The Disney Food Blog and Helping you plan your Disney Vacation is an industry unto itself these days.

Money: Walt Disney World is expensive. Yes, you can save a buck or two here and there even on your hotel stay by researching discounts and promotions that might be available when you are planning to go. In our case we doubled up and stayed in the same hotel room, but food and park tickets couldn’t be shared. We figured that we were looking at $2,000 each for our trip easily. Which in terms of Disney wasn’t bad especially when you considered we would be staying 7 nights which gave us nearly 8 full days to enjoy the parks and Downtown Disney.

Hotel: My preference has always been to stay on property because of the access to transportation and not needing to deal with traffic around Orlando on a daily basis. Bob was in agreement and we settled on the staying at the All Star Music resort. I’ve stayed at a couple different resorts at WDW and the Fort Wilderness campground in the past. For my money the All Star resorts are the best on-property hotels to stay at. They have the same amenities as most budget motel chains and are only missing a “free” breakfast in the morning, a microwave, coffee maker, and refrigerator (hint, hint powers that be at WDW). They have pools for that sometimes needed down time and reasonable on site dining. The only disadvantage is that they are a little far from the parks themselves so you do have to plan on at least a half-hour to an hour to get anywhere if you are using the on-site transportation, which I recommend. Driving and parking around WDW can be a hassle. Even if you arrived at WDW by car you will likely find it easier to keep it parked (there is a parking fee) than to hop between lots all day.

Some people really like to stay at a more upscale resort. This is fine if you really want the additional room decor or whatever. However, to my way of thinking there’s no need to spend extra money if you aren’t going to be spending much time in the room anyway.

Food: We also decided on something I had never done before and that was to get a Dining Plan (which worked out to 1 sit down meal, 1 quick service and 2 snacks per day). Doing the math we realized that we would not likely save any money doing this but we liked the idea of not worrying about paying for meals while at WDW. In my opinion this turned out to be one of the best choices we made and this old dog learned a new trick. Because of this we went to several restaurants I never would have gone to on my own and because we could make reservations well in advance of our trip the only decisions we made each day was were to eat lunch and get our two snacks a day! Breakfast wasn’t included in the plan so we also packed some instant oatmeal cups and a variety of granola bars along with a small travel sized coffee pot for hot water so we didn’t have to buy breakfast each morning at the hotel.

Parks: We chose the park hopper option (currently limited) so we wouldn’t be tied down to any one park and could be flexible if we decided to go somewhere else on any given day. Though the park hopper option is more expensive to me having the flexibility to go to any park we chose or more than one park on any given day is priceless. This may not be true of a one day spur of the moment visit – though I once visited three parks in one day – but is definitely worth it on a longer stay.

Other Considerations: We arranged for an early flight on our arrival day since our park tickets were good when we arrived even though our room wouldn’t be ready until later in the day. Likewise we were catching a late flight out on our last day as our park admissions were good all that day, too. Though we planned out our Fast Pass choices (currently unavailable due to social distancing) for most days we left the last day open as a “catch whatever we might have missed” day. At the time we traveled WDW still had the Magical Express, which as of this writing is scheduled to be discontinued, so transportation from the airport to our hotel was taken care of.

We also made sure to pack ponchos in case of rain, I was taking my trusty “fanny” pack to hold a portable phone charger, my phone, emergency credit card while in the park, sunscreen, and a couple granola bars. Bob was taking a larger backpack for a refillable water bottle, the aforementioned ponchos, and room for souvenirs. We also made sure that we had extension cords for our respective CPAP machines. In my experience you can’t always count on their being a power outlet conveniently located near your bed.

After a very long January and counting down the days to the trip, finally the time had arrived.

Our adventure was about to begin.

To be continued…

3 thoughts on “Grumpy Old Men on Tour: Walt Disney World

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