Boston’s Best|In THREE Days

Yep, I am in love. From the second I stepped into its crisp, fall air, Boston had me hooked. Why did I visit Boston? Well, after college it is easy to lose touch, especially when you and all of your friends are located in different parts of the country. So what do you do? Well we did Boston…and I believe this may become an annual thing (I hope), we pick a random city, meet up there and have one heck of a time.  If you are wondering why we chose Boston, don’t worry I’ll answer that question and more…Keep reading and see how Ileana, Megan and I took on (survived) Boston…and Halloween

WHY Boston?

  1. bostonleavesIleana and I had never been to Boston.
  2. Pinterest and Google, the more I read reviews and searched the “what to do” and “where to go” just got to me.
  3. Boston oozes with American history and I am a sucker for a good story, especially when it is told in a Boston accent.
  4. Fall. Boston is beautiful, during the fall, and I have been deprived of colorful leaves for far too long.
  5. The flights, even across country, are not astronomical. We all came from different cities and the best deals were with Delta Airlines and Southwest Airlines. I flew Delta, roundtrip, for $385.
  6. Finding an affordable/nice hotel, in a good location, is absolutely doable. It was important for us, as three young women, to be comfortable walking outside of our hotel and feel safe. (Hotel info in the next section)
  7. And again…Why not? If you like to travel, see as much as you can, when you can.

How we did BOSTON, in our 20’s

(Hotel, Restaurants, Bars, Sites and More Tourist Stuff)


The Boxer Boston

Stars(tripadvisor): ✭✭✭✭

Style: Boutique

Lobby & Bar: Quaint, warm and well decorated

Room: Deluxe Double| A little small, but just fine for three girls and our bags.

Staff: Extremely welcoming, helpful and available| The Boxer’s staff definitely made our trip easier. From booking popular attractions to genuine, personal suggestions, they went the extra mile to ensure we enjoyed our stay. 

{A few hotel pics}




{The Restaurant, the bars…and (some) Halloween.}

*With 3 days, 3 girls and a budget, we decided to have at least ONE nice dinner…We obviously stuck to that plan. Getting three girls, to be nice dinner ready takes away a lot of precious time.


Our “Nice Dinner” RestaurantAria Trattoria 

Featured Articles: Boston Globe, SceneBoston

My Order: Insalta Ceasar, Gnocchi con Aragosta…and a lot of Pinot Grigio. (The Gnocchi con Aragosta was absolutely mouthwatering.)

Overall: Aria Trattoria is cozy and intimate with authentic Italian cuisine-I’m Italian so I tend to be extremely critical of the cuisine.The restaurant is small, but that is one of its greatest charms. Make sure to make reservations.  


Sunday Night Bars…Oh and a diner

So being from Alabama, Sunday night isn’t usually a “happening” kind of night. Well, in Boston, Sunday is not different than Saturday or Friday. Obviously this was a little bit of a culture shock, but I won’t complain. One thing I will say, don’t go out in leggings, a sweatshirt and tennis shoes.  It’s a casual night, but not that casual- shout out to the Bostonian who gave us that fashion advice, you owe us all a few rounds of drinks. Seriously, but at least the bars were a BLAST. Going with the Bostonian’s advice- bar wise and fashion wise- we bar hopped and then ended the night with a greasy, delicious breakfast…Then we grabbed our bags and headed to the airport. Go big or go home, right? Below are the bars we visited (they were a blast) and the delicious (I’m being serious) diner. 

The Playwright Bar

Boston Beer Garden

South Street Diner


The Diner put your drinks in MASON JARS, I was pumped. Oh and a Bostonian friend!


With a little help from the staff, at The Boxer, we decided to do the Hard Rock Cafe Halloween Pub Crawl ($36 per ticket). Now that we all are a little older, the club scene isn’t something we wanted take on, we wanted to be in a smaller setting where we could sit and drink or dance a little…Oh and actually hear what the other person is saying.  Anyway, the tickets gave us access to multiple bars around Boston, some of which offered amazing drink specials. We had a blast, to say the least. Below are a few photos from Halloween 2015↓


I obviously didn’t get the Super Hero memo. (Ileana– Wonder Woman, Megan– Supergirl)

This was my face for most of the night. No I did not realize trying to look “vampiresque” would be so difficult. In some photos I look like I ate dog poop, not attractive…My husband is so lucky and so are these lovely ladies ↑


See, what is with my face.

 {Site Seeing|| Being “Those” Tourists}

Yet again, the staff at The Boxer helped us figure out what we should/could see with the short time we had. We opted to purchase tickets for the Old Town Trolley Tours. This trolley takes you along the Freedom Trail that goes all around Boston. The first day we just road the trolley and took notes on what we absolutely wanted to see, since there was so much to see. The second day, after recovering from Halloween and running low on time, we rode the trolley to our absolute, HAVE-TO-SEE sites. The trolley runs from 9am-5pm, so naturally we hopped on at 1:30pm (BOTH days). In all honesty, I can’t complain. We were able to see a lot from just riding the trolley and one of our guides, hands down, was the funniest/sarcastic person I had ever met- that alone made the trolley pricele$$. Below are pics from the “few” sites we were able to see. Again, no regrets. We had a blast!


In Front of Trinity Church


Massachusetts State House


The Children’s Museum


On the Replica Boat at the Boston Tea Party Museum



The Old State House, Site of the Boston Massacre

A {Few} Outfit Details


Sweatshirt: Stress Less Hoodie

Vest: Excursion Quilted Down Vest (Similar)

Pants: MOTO Super Ripped Jamie Jeans

Shoes: ‘Benicio’ Ankle Boot

Purse: Cedar Street Maise

Hat: Crochet Beanie

Sorry for the blurry picturebostonteaparty

T-shirt: La Luna Foiled Muscle Tee (*On Sale)

Button Down: Flannel Shirt

Vest: Factory Quilted Puffer Vest (*On Sale)

Pants: MOTO Authentic Ripped Jamie Jeans

Shoes: Grey Del Rey Sneakers (Slowly becoming my favorite shoes)

Scarf: Brixton Grace Knit Scarf

The Random Pictures





Replica of the Boston Tea Party Ship


Taking Selfies= Tourist Rite of Passage



Isn’t She Just Adorable? 

I would have liked to take more pictures, but my camera succumbed to the “shift” in the overhead bins…Yeah, it’s broken. Apart from the injured camera, this trip was a success! Boston was everything we could have imagined. The city is unbelievably beautiful, there is always something to do/see and it’s not overwhelmingly large (easy to get around). Hands down, this city is full of character and I cannot wait until my next trip to Boston. There is so much more I want to see! I will visit again, soon. Until then, Boston, you were awesome.




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