Boston in January Makes an Interesting Vacation

Who in the world takes a “vacation” to Boston in January?  For those of you who don’t know, my husband Tyler works for a company that is headquartered in Beverly, Massachusets, just outside of Boston.  Most of the employees work remotely across the country so twice a year the company hosts company-wide meetings for all of the employees to work together in person and discuss all of the exciting business updates.  So, in January, they hold their first meeting of the year and couple it with an after-holiday party.  This company rocks and they pay for spouses to fly out to go to the party as well which is pretty rad.

I’ve never been to Boston before so Tyler and I thought we’d like to spend a long weekend there where I could explore the city in all of it’s wintery glory.  Additionally, one of our best friends Connor lived (*he moved across the country literally days after our visit) in Boston so it was a perfect excuse to stay a little longer.

We arrived on a Wednesday evening and headed over to East Boston for dinner.  We ate at a local pizza joint and had a waitress with one of the most Bostonian accents you’ve ever heard.  Tyler had meetings on Thursday and Friday so I  took advantage of my ability to work remotely and did some of that coupled with some sightseeing.

On Thursday, I spent WAY too long looking for the Boston Marathon finish line on Boyleston Street.  I didn’t want to look like a tourist using my GPS so I kept walking up and down looking for it.  I think I passed it 3 times before I found it.  At least I got my 10,000 steps in that day… I then checked out the Boston Library and did some work before meeting up with Connor for dinner.  We split the most glorious lobster mac and cheese for dinner and it was the most heavenly item I ate during my entire stay in Boston.  It was great to catch up with him and check out some of the sights around the city.  He even taught me how to ride the Subway like a local.  I’m pretty much a pro at the Boston “T” system now.


On Friday, I again met up with Connor and we took the “T” over to Harvard.  Connor and I met in the days when we both worked for KOHLER in Sheboygan, Wisconsin.  We played this fun game in Boston where I took the “T” from one location and he from another and we met up in one of the underground subway stations.  What a far cry from our old adventures in Sheboygan…

We walked all around Harvard’s campus, stopped in a couple of bookstores, had a bite to eat, a couple of coffees, and again enjoyed catching up after many months of not seeing each other.  Here are a few photo highlights from our afternoon adventures…

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That evening, Tyler and I got all fancy and headed out to the company party at the New England Aquarium.  During our walk through the aquarium which has a 3-story tank full of interesting and exotic fish, I came to the realization that I might be a little scared of fish which is great because we’re planning on snorkeling the Great Barrier Reef when we’re in Australia in March…yikes.

Apparently, this terribly awkward angle selfie and the giant sea turtle are the 2 best photos I have from this event…  Use your imagination – there were lots of cool fish.

On Saturday, I taught Tyler how to take the “T” and we headed over to Connor’s apartment where we would stay for the next 4 nights – more on that later.  Once we met up with Connor we trekked (via Uber) over to Sam Adam’s for a brewery tour.  As Connor’s mom pointed out, we’re from Wisconsin, why did we travel all this way to do a brewery tour?  Because we love craft brews and we always like to impress the locals with our extremely strong knowledge of beer and the brewing process.

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The remainder of Saturday and Sunday were spent checking out a combination of The Freedom Trail which showcases many of the historic locations throughout Boston as well as popping into local food joints and watering holes.  The snow began Saturday night and basically didn’t let up until Sunday evening.  I’m not sure most people thought walking The Freedom Trail in snow and freezing rain.  But, we’re from Wisconsin so I guess it didn’t bother us too much.

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Monday rolled around and Boston was suddenly one giant sheet of ice.  We were going to enjoy the city for a few hours before flying home that afternoon.  We got to enjoy Boston for a little while longer (2 days to be exact) when our flight was canceled 4 hours prior to when we were supposed to depart.  It was freezing cold as we wandered the city that morning, but we were able to “make way for ducklings” and hit up the only bar “where everybody knows your name”.

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Thank goodness, we had a great friend (who at this point was out of Boston on a job interview across the country) who had given us his spare key and allowed us to stay in his apartment while we were stuck in Boston until Wednesday.  Even better, our remote work jobs allowed us to enjoy these extra couple of days without interruption.  #Blessed

We finally made it home where we were greeted back in Milwaukee where it had snowed twice since we were left and our car nicely buried in the airport parking lot.  More shoutouts go to our amazing friends Matt and Laura who shoveled our driveway and sidewalks while we were away so we were able to easily pull into our driveway once we arrived home.  #ExtraBlessed


So what started as a little work trip turned long weekend turned full week vacation.  Boston was a blast and I’m excited to visit again someday…hopefully not in the depths of winter.

Here’s probably my favorite picture from the entire trip when Tyler, Connor, and I walked across the pond in the Boston Commons which was frozen over carrying Connor’s dry cleaning.  #SoExtra #SoWeird #FriendsForever


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