One of the questions I get most often asked is how long it takes to plan this trip. I’m not actually sure what the answer is, as it happens over a series of days and weeks, a little bit at a time. But honestly, probably not as long as you might think. You have to be OK with your desktop looking like this for a while:

But a big chunk of the planning happens in the first two hours. Find the MLB’s daily schedule, and open a tab in Expedia, and start matching up home games and possible flights. It’s a cool, nerdy puzzle to solve. If you’re into cool nerdy puzzles.

Last June I had quite a bit more freedom simply because there were more stadiums that I could choose from. Now I’m up to 16 that I’ve already seen, so I figured adding another 10 this summer would be trickier. It was, but not by much. I think the fact that I had been through the process already helped counter-balance the fact that the planning was a little trickier.

I’ve mentioned this before, but it bears repeating: I fully admit that I have pretty much the perfect schedule to be able to pull this trip off: the school where I teach, Palo Alto High School, is finished on June 4. My wife and kids, who are in the neighboring district but one that has a vastly different calendar, aren’t done until the middle of June. So I have a couple of weeks where they’re still busting their butts working all day long while I’m riding the high of early-summer freedom. Then in August, I start back about two weeks before they do. It would be great have matching summers, of course, but that’s not been in the cards. It also helps that I have an incredibly understanding family who isn’t overly interested in baseball. I’m not entirely sure they’d want to go on this trip even if they could. This week-and-a-half has been granted to me as a gift and I don’t take it lightly!

At any rate, back to helping you plan YOUR trip. Like I said, start by looking at the MLB schedule and seeing what works. Then start punching them into a Google Doc. It might look something like this:

That’s a more polished version, but it was pretty messy for most of yesterday while I was trying to piece it together. While last summer I was mostly on the West Coast and didn’t get any further East than Cincinnati, this summer’s trip will be much more on the Eastern Seaboard. One perk there is that I’m not going to have to fly nearly as much and I can combine a couple of parks into the same visit (the Mets and Yankees, and the Orioles and Nationals). I’ve also booked the bus for two of the legs of the journey: from Pittsburgh to Philadelphia and from New York to Baltimore. Some of this was tricky of course, but most of it fell into place pretty smoothly. I only found one possible time that I could see the Yankees and the Mets on back-to-back days, and so I started with that in the middle and worked upward and downward from there. And my sister and her family live in New York, so I knew I could make that the centerpiece of the trip.

You’ll note if you look carefully (I wonder how many people are looking THAT carefully!), that I snuck a minor league park on the schedule for the first time. I don’t think it violates the spirit of the journey, which who cares since I’m making up as I go anyway, but it also will save me some money, allow me to spend a little more time with my nephews, and also save five stadiums for whenever the next trip might be. Plus I’m guessing the Long Island Ducks will be pretty entertaining! I had a shot to see Tampa that day but this will be way less crazy and it still makes 10 stadiums in 10 days.

Another lesson I learned from last year is that using ‘Hopper’ is a great way to save money. The flights listed on my Google Doc above aren’t booked yet, other than Milwaukee-Pittsburgh, but they are all loaded into the Hopper app. For nearly all of them I’ was told to wait before booking because prices would likely drop. When they change, Hopper sends me a notification that I might want to book. Maybe you all know this already, but if not, it’s worth getting.

The next step will be figuring out places to stay; if you live in any of those cities and are interested in housing a random guy (me) for a night, let me know! Otherwise my plan is always to find the cheapest possible place to stay, regardless of how few stars it has. There’s way more character in a $23/night motel than a $350/night resort. And by ‘character,’ I mean ‘weirdos.’

I also want to launch a Twitter handle (@StadiumsTen) that is specific to this journey, rather than using my personal one. I’d still love to figure out how to connect to more people along the way and make this a journey sponsored by Major League Baseball, representatives of which are surely reading this blog right now and thinking the same thing. (note to MLB reps: you can contact me via email at bwilson3560@gmail.com). Just think of how cool it would be to have me as the face of your new ’10/10′ marketing campaign. Right? I mean… right?

Looking forward to June! Maybe I’ll see you then!