Initially, the flight was going to be from Washington, D.C. to Boston, Massachusetts but herein lies the trouble with flying standby: it’s never a guarantee you will get on the flight you want.

The night before we were leaving for Boston, we looked up the flight schedules to see what they looked like.  D.C. to Boston was not going to happen.

To work around this, we took a 40min Uber ride to the Maryland airport – only $40 – with a likelihood of getting to Boston.

Well, just our luck, we were not making it to Boston right away.  Going to Providence first was our best bet, so on we went.

Providence, Rhode Island

I’ve never heard anything remarkable about Rhode Island to begin with, and my honest opinion?  It’s not that remarkable.  GRANTED, we were only there for a quick bite to eat and stroll around town.  We were probably there two hours, tops and that’s one city in one state.  To me, it seemed Brown University is Providence’s shining glory.

I may have a bad taste in my mouth about it because the goal was to hit up Boston and check out RI only once we had picked up our car.  The unscheduled detour was no fun to me and with a glitchy day of three missed flights and a crappy Uber experience, I had written off the city.  That’s unfair of me.

Oh, the Uber experience?

We got in her car, after she told us she had stuff in her trunk so we’d have to put our luggage in the backseat (where are we supposed to sit?).  She proceeded to tell us in a thick Jersey accent that due to “new Uber policy” she couldn’t drive us to Boston.  Okay, so can you cancel the trip?  No, because it already started.

It was pretty bogus so I had her drop us off down the street, then proceeded to send Uber a message.  Go Uber – they sent us a full refund ($2.86 each. Yea, baby!)

A 1.5hr train ride to Boston was a possibility, but we decided we’d just try Uber one more time to see if that driver just happened to be full of shit.  And guess what?  She was.

FINALLY, we were headed to Boston.

Boston, Massachusetts

One thing I was really excited about going into Boston is that my favorite artist (Amanda Palmer / The Dresden Dolls) is from Boston.  If you’ve never heard of them music, give it a listen.

I was listening to The Dresden Dolls song “Boston” as we were approaching and heard her lyrics “in my apartment in the south end” and lost my shit because, unbeknownst to me, her old apartment would be a mere FOUR MINUTE WALK from the AirBnB we had booked… in the south end.

The apartment is called the Cloud Club and Amanda Palmer writes about it in her book The Art of  Asking.

That’s it!  I know it may not look like much but there’s a huge garden in the back.  The building is composed of seven studios and it’s essentially an artist commune.  Very cool for me to see.

By the time we had arrived in Boston, it was already nighttime so after a 30min stroll around town, we went back to the AirBnB to crash.

The next morning was the start to an ambitious day.  We were going to try and see as much as possible in Boston, then pick up a rental car in the evening for our drive to Portland, Maine.

Our first cool sight was a community garden… in the city!

It went on for the length of probably two blocks.

After more walking, we ended up in Boston Commons, where the Freedom Trail began.  The Freedom Trail is essentially a red cobblestone line that goes from one point of interest to the next, all over Boston.

This awesome dude greeted us as we entered the Commons:

How can you not tip this guy?  This is artistic dedication.  Man has a vision.

The Boston Common itself is beautiful and inviting.  Look at those boat rides!

From there, we bumped into the Cheers bar.  Neither my companion nor I drink, so we didn’t need to stop in for a beer, but we did skim through the merchandise and look at the bar.  I never really watched the show but I’ve seen an episode or two.  Still cool to see!

Then we got lost wandering down the cobblestone-paved sidewalks.

Capitol building with a dome (reminiscent of Temple Mount in Jerusalem).

Ben Franklin’s tomb:

Poor John Hancock has the most phallic tombstone of all time.  And then it says “This memorial erected.”  My God.  They must have hated him.

Site of the Boston Massacre, where British soldiers killed 5 people while under attack by a mob:

It’s really cool to see these super old buildings in the midst of a growing city.  I found Boston to be beautiful in both its history and personality.  VERY busy this time of year, though (July).

The home of Paul Revere (below).  They had tour groups going through it but the crowds were insane, so we decided to pass.  In a less busy month, I’m sure it would be really neat to see!  If you’ve seen it, write a comment down below to let us know how it was.

Also, I’m aware this photo’s composition SUCKS, but the it’s basically pressed against the brick building behind it and the views from the front were no good either.

The end to our trip was getting cannoli at Mike’s Pastry – $4 worth of goodness.

They had all kinds of flavors, from strawberry to pistachio to peanut butter.  LOTS of options, but a HUGE line.  Line moves quick though, so don’t fret.  And remember to bring cash, because they don’t accept credit cards!

From here, we took an Uber to the airport where we picked up a rental car and headed to Maine.

Boston is absolutely a city I could see myself living in.  It has its quiet neighborhoods just outside the city, its historical significance, delicious sweets, large parks, and cobblestone roads.  I would love to get back there some day.

Providence?  Maybe it deserves a second chance.  Please feel free to rip me a new one in the comments.  Or just comment on the post itself with questions, concerns, or anything else!