Boston: Cinco de Drinko

Taking a quick break from our Cuba trip to ramble on about my most recent escapade: Boston. 

It was a two day thing, and before you ask what I already know you’re going to ask, (How can you afford it?), the flight was $138 round trip with Jetblue Airlines. The Airbnb was $229 and I split that with my friend Diana. Did you know Airbnb pays $200 for every host you refer? Yup, and I did just that so my $200 credit covered my portion of the stay. I parked my car at the airport, The Parking Spot, as parking is only $9/ day; an Uber alone would cost me $60 to and from. Note; to get this cheap fare, I had to take the shuttle to my terminal so please be aware of this when planning your departure.

Okay, so my flight was interesting as it was delayed 5 hours. Apparently there was some legal issues with the crew on board. They did not have the permission to fly directly to Boston so they had to fly us to Orlando first, switch crews, and then fly to Boston. There were a lot of angry, upset people on board but hey, what can you do? No point in being upset over the things you have no control over and I was not going to start my staycation with any ill feelings. The Uber to the Airbnb was $25.

Let’s start off with our Airbnb. It was a quaint little space; we shared it with another couple (although we never saw the guy). IT DID NOT HAVE AN AIR CONDITIONER. I missed that part in the fine print. If you know me, I sweat profusely and my apartment is always set to 65 degrees. First world problems, I know. Luckily, the weather was exceptionally nice so the windows were propped open and all was good with my perspiration. Diana and I head for brunch at a place called Deep Ellum. We noticed the majority of the food offered was Mexican, and it was surprisingly good.

We take in the environment and decor as we eat. (Yes, I consider us part of the decor.) 🙂

Once we finish, we walk to nearest station to catch the subway. The public transportation in Boston is great, traffic is horrible, and parking is horrible.

We purchase a $62 two day trolley ticket that will take us to all the historical and scenic parts of Boston. It’s a small city so when Diana asked her Uber driver what was good to do there, his response was, “Eat and drink”. Perrrrrfect. Apparently, they love to celebrate Cinco de Mayo as well. We decide to split scenic stuff and drinking/ eating over the two days. We end up having appetizers and drinks in North End, and walk around to explore this part of town a bit.


We hop back onto the trolley, it came every 20 minutes, and admire the views while we head back to downtown.

As we’re nearing our stop, we notice several bars and restaurants that are EXTREMELY PACKED. We pick one to go to and decide to eat there.


We’re pretty surprised at how packed all the surrounding bars are. It’s barely 6pm and you can barely walk into these places! We settle on a more calming setting. I stare at our bartenders attire and laugh, I have the same outfit. No really, check it out….


We decide right there to make it an early night and be home by 10-11pm. We have a couple cocktails and head to the next place. It consisted of huge drinks, tequila shots, and friendly man named Scott who was from Hawaii.

We soon realize our “chill night” was not going to be so chill. We find a dive bar with a great singer, get into some super deep and serious conversation, take a few more shots, and order an Uber.

A crossing of a railroad, a visit to a grocery store, and one purchase of a whole rotisserie chicken later…and we’re finally home.

Next morning, we arise bright and early to start our day. We must have been loud the night before; our lovely roommates placed ibuprofen and Advil on the kitchen table. (SO SWEET.)

We take the trolley back to downtown and head to a popular brunch spot. Diana’s feeling a little hungover but I tend to bounce back like a freak of nature so I order a mimosa.

Diana wants to visit Boston commons so off we go.

From there, we map out our remaining destinations to visit. Fenway park, Bleachers Bar, and Quincy marketplace…which we’re told are a lot of good bars there. We hop on the trolley and head to Fenway. We go to the bar called Bleacher’s Bar. They’ve got a Cinco de Mayo theme going and half the bar had sombreros on. This is a pretty cool place as they have a wall opened up as a front row seat to the baseball arena. Diana and I order drinks and sit and talk. She heads to the bathroom and I notice 2 guys sitting behind me with sombreros.

Me to guy #1: “Hey, how attached are you to your sombrero?”

Guy #1: “Pretty attached.”

Me: “I’ll buy you a shot for it.”

Guy #1: “No way, $700.”

Me: “$700?? Wtf…Is it an authentic hat made in Mexico or something? Bullshit. What about you?” (Looking at guy #2)

Guy #2: “No.”

Three shots later, I’m wearing his sombrero hat and Diana and I leave to the next bar.

The next place is a drive so we take in all the historical buildings and background our tour guide is giving us.

We stop at an extremely packed bar for a margarita. We’re the only Latina’s and I’m wearing a sombrero. We get a lot of looks and Spanish (somewhat) comments; it’s funny.

Then we head to Quincy marketplace and enjoy a show from some street performers. These are some legitimate entertainers, and they don’t want your $1 tip; they won’t even accept your $1 tip. $20 and up…and they absolutely got it. They must have made $400-$500 easily from our crowd alone.

We finally hit up the Quincy bars and the rest of the night is a little bit of a blur.

Warning: the following displays me as an extremely bad friend which I totally was and completely regret. I meet a group of people and while Diana is ready to go home, I am not. I ask if it’s okay to stay with them, and she agrees. Note: we have a 7am flight so staying out WAS NOT A GOOD IDEA. She takes an Uber home and I head back to their place an hour later and end up crashing there.

I wake up at 6am to 15 missed calls, 4 text messages, and a voicemail from Diana. Diana (SO CLUTCH) had to pack my bag and take it with her. She woke up like a responsible person at 4:50am and headed to the airport. She had no choice but to check my bag to Houston. (I live in dallas.) I rush to the airport, luckily where I crashed was only 8 minutes away. Rush through security and make it to my gate as they were doing last call. I feel horrible and apologize profusely and while she was initially annoyed and worried for my safety, eventually found it humorous. I’m wearing last nights clothes. It’s a mess. I’m a mess. Boston-1 : Priscilla-0

I pay her for half the Uber it took for her to get home and to the airport; and the cost to check my bag. We recap the whole night when we get to our respective homes. It was interesting, it was hectic, but most importantly….it was a blast.

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