#107. Boston (Friday, July 31, 2015)

What was your best day…of taking an average family trip?

Thanks to the deep regret that remained from my younger years (#111), my mom could’ve suggested literally anywhere for this five-day family trip and I would’ve been down.

Still, Boston turned out to be one of the better possible picks.

We packed a lot into the trip, visiting most of the notable Boston landmarks along with Newport, RI and West Point, while staying at an absolutely massive hotel in Burlington that was an experience in itself.

But the highlight of the trip would have to be the second day, where in the span of a morning and afternoon we went on tours of Harvard, MIT, and Fenway Park – the (only) three iconic things I’d associated with that famous city for as long as I can remember.

Even though my brother was the one going into his senior year of high school and applying to universities in the fall, Harvard and MIT were more for me than him. I’d tried the whole “do the SATs and apply to Ivy League schools” thing eight years earlier and failed miserably, and so in a way I was hoping to live vicariously through him getting accepted to one of those schools – even though he never really had a strong interest.

In any case, actually setting foot on the campuses and interacting with them did a lot to break the (insecurity-based) aura I had placed around the schools since my rejections. It was the usual “these are all normal students and people just like I was/am and these are ultimately just universities (nothing more) like the one I attended” experience that comes around to everyone sooner or later. But I was legitimately surprised by the very cool yet down-to-earth MIT vibe, with thanks to the most self-deprecating tour guide I’d ever had. (Though this was detracted in part by the members of some Chinese cultural group aggressively accosting my brother and I while we were waiting for our tour.)

As for Fenway Park, beyond the awesomeness of walking through ever odd corner the hundred-year-old ballpark, the coolest part was during tour when we saw a long line of Red Sox players standing along the left field foul line – in the middle of doing the Ice Bucket Challenge. All the while, Chris Archer from the visiting Rays was just chilling in the outfield by himself not noticing all this while methodically doing his drills.

But if that wasn’t enough baseball for one trip, that day also happened to be trade deadline when the Blue Jays acquired David Price and a several other key pieces that immediately led to a wild two-month playoff push. Two months whose pure magic all felt like a continuation of this already pretty great visit to Boston.

Much more on that later.