Finally Visiting Boston

I've flown into the Boston airport a few times on my way out to Cape Cod (where my company, BackOffice Associates, is headquartered) but have never actually seen the city.  A few friends from the company have been inviting me to come up to hang out and I finally found time to make it happen.  After my recent breakup, and the discovery that she was already in another relationship, I really needed a weekend to get my mind off of it and distract myself with something new.

Liberty Hotel lobby and former jail

Instead of flying home to California for the weekend, my client bought me a train ticket to Boston on the Acela (bullet train).  It took about 3 hours and I tried to work on the ride but the internet signal was way too inconsistent to get anything done.  I had never taken a high spreed train and I'll definitely do it again if I'm going to one of the major east coast cities.

I took a subway from the train station to a stop right near the hotel where I'd be staying Thursday night.  My Starwood points got me a free night's stay at The Liberty Hotel. Since the guys from my company worked similar schedules and were traveling in on Thursday night, we all agreed to meet up on Friday afternoon.  I had almost an entire day to myself to explore and sightsee on my own.

I had no idea how cool the hotel would be... it was re-purposed from the Charles Street Jail, built in 1851.  There are placards and videos that tell you about its history.  The hotel is very upscale and I definitely recommend staying there - it's really nice (especially if you can stay for free using points because it is kind of expensive).  I had dinner in one of the hotel restaurants and then wandered around Boston Common after dark since I didn't have anything else to do.

Tour guide in front of Paul Revere's grave

The next morning I retraced my steps to Boston Common for a Freedom Trail Walking Tour (~$15).  It started at a kiosk along the edge of the park and took me all through downtown Boston.  The guide knew a lot about the history of architecture, politics and characters that gave Boston its prestige over the ~2.5 mile, 2 hour time.

A few of the highlights of the tour included a burial ground where John Adams, John Hancock and Paul Revere were buried.  Note that Paul Revere's place in history is a lot of good PR!  There were other riders that night but he's the only famous one.  The Old State House was where the Declaration of Independence was read for the first time.  The Boston Massacre occurred just a few blocks away.  I hadn't heard about many of the people, places and events since at least US History in high school so it was cool to brush up and see them in person.  It's a cheap and informative tour to take and a MUST DO in Boston.

Rooftop panorama of Southie

After doing a little wandering of my own around the campus of Harvard, I went over to Martyn, Chris, Brian and Mike's condo in Southie to meet up with them.  A few of them had gone to school in Boston and all were from Massachusetts.  Chris and I actually took our first training class with BackOffice together in 2008 and Martyn had been our teacher. We caught up for a while and then went out to some bars that they frequent.  Our first stop was Jillian's right next to Fenway Park.  I honestly don't remember the names of the other places but I do know this... those guys know someone at every bar, whether it be a bouncer, doorman, bartender or waiter.  They're definitely awesome tour guides and have the hookup on cool places and drink deals.

Sailboats with Boston's skyline

The next day was a slow one to get up.  We drove around the city a bit and then took a Boston Duck Tour ($30) in the afternoon which is something a few of the guys had never done.  It was fun to be outside and the driver was entertaining, but I don't think it was worth the cost.  We got cleaned up and dove into some seafood at Legal Seafood.  Chowder, clams, mussels, shrimp, you name it, we got it.  Seafood is definitely another must do in Boston.  After that we hit the bars again... and again, I don't remember the names.  The next time I go back I'll have to note them down.  All I know is that they knew a bartender, 5 of us sat in a bar for a few hours and our tab was $60.  Awesome.

On Sunday morning I linked up with my friend Dana, a former coworker at CNN.com that moved to Boston a few years back.  She invited me to watch the Head of the Charles Regatta on the Charles River near Harvard's campus.  Dana rowed in college so she could explain all of the rules and strategy as the different classes and teams raced down the river.  The weather was perfect and her friends were tailgating for the race.  It was a nice relaxing end to the weekend.  I'm definitely going to hit the city up again.  The guys were great hosts and really showed me a good time.

Our tailgate spot for the Head of the Charles