Paper, Planes & Pinot

In Other Words… Stationery, Travel, and All Else that Matters

Travel Thursday – Boston

Three years ago, the beau and I took a trip to Boston to celebrate July 4th.  We decided to save some money and take the Megabus from DC to Boston.  To try to get good seats on the bus we arrived at the b pick-up location an hour before the bus was scheduled to depart.  When we boarded the bus, we thought we were the luckiest pair of passengers since we scored the last 2 seats beside each other on the packed bus.

We quickly found we were not so lucky.  Not only were we in the 2 seats right in front of the bathroom, but the BF’s seat was broken and he had to pull his seat forward EVERY TIME someone used the bathroom.  Thankfully, we were young and in love, nothing could break us on our weekend adventure (not even a smelly bus bathroom and no sleep on a red eye bus ride).

Still, this experience taught me a very important travel lesson.  As adults with hectic schedules, vacations are priceless.  My tip to is to not sacrifice your time while on vacation.  Don’t be stingy.  Opt for the mode of transportation that gets you to your final destination the quickest.  Spend the extra $$ for a better flight time.  Pay a little more for convenience to get more time out of your vacation!

Now back to Boston… Boston is an AMAZING place to visit during the summer.  My first trip to Boston was for a sorority convention.  Touring the city with my sorority sisters was a ton of fun.  It unfortunately was a quick trip.

Four years later my boyfriend and I were trying to decide what we wanted to do for July 4th.  The choice to plan a trip to Boston was easy.  We had heard the fireworks show was amazing, and the Red Sox were playing.  Done deal!

As a planner, I of course did research and made an itinerary.   Here are some of the things that we enjoyed that I would consider MUST DOs:

The Freedom Trail

Walk the Freedom Trail.  It is about a 2 and a half-mile walk through the historical sights of Boston.  We did this as a self-guided tour, took our time taking in the sights, and also were able to veer off the trail whenever we saw something else that caught our eye (aka whenever we needed an ice cold beverage).  You learn a lot on this tour and are also able to see a good portion of the city.


My advice is to wear comfortable shoes.  Most of the trail is on cobble stone so although wedges can be comfy, you may struggle a bit if wearing them.  Also, the trail ends at the Bunker Hill Monument.  After walking the entire trail, you will want to cap it off by walking to the top of the monument.  To ensure you make it to the top wear good shoes!


I am not going to lie, making it to the top of this was a struggle for me.  First off, I did not take the advice that I dished out above.  I wore sandals that did not fare will with our hilly walk and the cobblestone.  Once at the monument it was a claustrophobic walk up to the top.  I do not do so well when I am hot, let alone while climbing up a monument behind sweaty children.  Nonetheless the view when you get to the top is beautiful and worth it!

New England Holocaust Memorial

Boston is full of history outside of the Freedom Trail.  The New England Holocaust Memorial is a beautiful tribute.  There are no words to explain how touching this memorial is.  Just imagine a memorial being built in the middle of a busy intersection, that many take the time to visit and absorb.  I definitely recommend taking the time to stop here and take in the memorial.

Harpoon Brewery

This is a FUN Brewery tour.  The guides bring beer with you along the tour and make sure that your glass is never empty.  Trust me, I was brown out before the tour was over.



You also get to sample beers after the tour!  I fell in love with the UFO line; you will too!

One tip is to get a reservation for your tour.  Harpoon Brewery is popular.  We ended up putting our names on the list and having about 2 hours to kill before our tour started.  If this happens to you, do not fret!  There are tons of places to eat around Harpoon, so you will be able to enjoy some fresh seafood if you have to wait!

Quincy Market

Quincy Market has tons of shops and FOOD.  This is the perfect place to spend the afternoon browsing and getting some Boston souvenirs.  There are great retail stores but also craft booths.

Mike’s Pastry is famous for its cannolis, but there are also some great cannoli choices at Quincy Market.


Little Italy 

The famous Mike’s Pastry (mentioned above) is located in Little Italy.  I unfortunately did not have the chance to make it here but I hear it is amazing!

I love everything about Italian food.  The carbs… I love.  The wine… I love.  The flavor… I love.  My advice to you about Little Italy is to look on Yelp and go grab yourself a good meal.  If your phone dies no worries, just look for the longest line and wait in it.  Trust me the wait will be well worth it!

Red Sox

A trip to Boston is no trip at all if you do not go to Fenway.  We happened to go on July 4th and it was amazing!  Nothings screams AMERICA like Baseball.




I love tailgating, but it is pretty hard to do if you are a tourist with no car!  Luckily there are tons of bars and restaurants around Fenway so you can easily get your buzz on prior to entering the stadium.



The fireworks in Boston are the BEST I have seen.  You would think that the fireworks show in Washington, D.C. would be the best I have seen, but the Boston show is 10x better.  Fireworks. On. Steriods.

I will not be posting the fireworks pictures that I do have.  It gives the show no justice.  You will just have to head to Boston to see them!

Now for the Boston fireworks struggle: we got to the show about 4 hours early and had a tough time finding a place to sit.  Luckily, it was just the beau and me so we eventually found a little plot to sit on.  1st Crisis averted.  During a period of 4 hours when you have been drinking, you will want to use the bathroom. . .so will thousands of other people.  Make sure you get in line BEFORE you are about to burst.  Also, ladies, bring toilet paper!


There is NO shortage of bars in Boston.  Anywhere you go you will have a good time, but for tourist sake you have go to the original Cheers Bar!


Wherever you choose to celebrate the 4th, I hope that you have an awesome time!  Boston has been checked off of my list, and it was AMAZING!


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