Boston Travel Guide

B is for Boston

Elle Magazine named Boston one of the most instagrammable cities. In my best 2 Chainz voice, I’d have to say,” Truuuuuuuuu.”

When my friends Thomas and Ty invited my friend Alan and I to Boston this year, I of course had to move some stuff around to make sure I didn’t miss out on our annual Boston trip. Boston has easily become one of my favorite cities as of recent and I really think you should add it to your list of to-dos.


I am lucky enough to be able to crash with my besties when I come to town, but there are plenty of Airbnb and Hotels options. My biggest suggestion would be to stay somewhere centrally located so that you can easily walk to attractions or catch the train. You can Priceline express deal a hotel in the city for about $80/nt on average or rent an entire home on Airbnb for as low as $70/nt.


From the airport into the city I’ve always ubered. Expect at least a $30 ride, but if you travel with a group you can obviously split and make it cheaper. Once you’re in the city Boston has several modes of transportation.



The T (train): rides are about $3 per trip.



Water Taxi: I’ve never done this but you can take a water taxi from downtown to airport & I absolutely plan on doing that next trip.


Quincy Market – an indoor food hall with like a billion different options of food to eat. Quincy Market in is Faneuil Hall and there are plenty of restaurants and shopping all around the market. I literally made the boys stop with me at Sephora to get a new lipstick before heading to an Irish Pub.

Parish Café – bomb (dot) com sandwiches & tasty drinks. The eggplant parm is to die for.

Union Square Donuts – if you do nothing else on your trip to Boston, get a Union Square Donut.

Article 24 – I think I love this place because they have a live band that performs in the evenings. This restaurant is two stories and has a different menu on each floor. We got drinks on one floor and ate dinner on the other. Be sure to check it out and rub the furry painting downstairs.

Tasty Burger- after a long night of turning up. Tasty Burger will be your bff. They have amazing burgers, but literally one of the tastiest Veggie Burgers I’ve had since I stopped eating meat. Some locations even have a bar so you can continue partying after you leave the bars.


One of my fave things to do in Boston is pub crawl. With Boston being such a walkable city you can easily just do this your entire trip. From rooftops to speakeasy’s you can easily find a drink or two to fit your fancy.

Top of the hub restaurant at the Prudential Tower – Do you want fancy views of the city while drinking a champagne infused drink? Well of course you do. I love a good elevated view of the city while sipping on a drink with my pinky out. Make sure to go during the day to “instagrammable” photos of the city.

Painted Burro – 4 words: Spicy El Diablo Margarita. I loved Painted Burro because they had some of the most unique Margaritas I’ve come across. They also have a free photobooth that we heavily took advantage of and for a small fee you can control the bars music through touch tunes. My friend Alan chose to play Christmas music, it’s spring time.

Carrie Nation – Old Speakeasy bar. This bar reminds me of a bar where Beyoncé would have performed her routine for the song, “Dance for you.” Very dimly lit and grown and of course sexy. I love the speakeasy feel and grown up vibes.

Hong Kong – home of the scorpion bowl. My number one suggestion would be to not drink an entire scorpion bowl by yourself. This is your typical bar, but downstairs you can sing karaoke and of course dance your life away. Always one of my fave stops on a Boston Trip.



Harpoon Brewery – Harpoon is prob my fave brewery. Mostly because of the warm pretzels, but the vibes in here are such a good time. Every time I go to Harpoon I meet new and interesting people. The line to get in Harpoon can be a little lengthy but well worth it. Whoever the DJ is in here is all my best friend forever ever, even though we’ve never met. I’ve never done a tour of the brewery, but might be worth it for you nosey folk.

Aeronaut – I loved Aeronaut because everyone was playing games. My group brought an intense game of Jenga with us that kept us pretty entertained. But if you don’t happen to have playing cards or a random set of monopoly with you, they do have a Nintendo 64 that you can play with. The flights of beer are tasty and tons of different options. They also have food for sale and like a mini chocolate factory thing in the back room near restrooms.


The boys are really really cute in Boston so, going out and mingling is always well worth it. Some of my go to places are:

Cask & Flanagan


The Lansdowne

Bill’s Bar

Bell in Hand

  • One of these bars we def got kicked out of. Obviously because we were the coolest kids in there and they wanted the locals to get their shine. But nonetheless always a good night in Boston.



Fenway Park – If you are lucky enough to be in town during baseball season def make your way to Fenway park for a game. We bought tickets 30 mins prior to the game for around $10 and even got free bobbleheads.

Bowl Haven –I suck at bowling in real life. But I literally beat the brakes off the boys at Bowl Haven. This place in old school candlestick bowling with little tiny balls you roll at candlestick like pins. They also have the best flatbread I’ve ever tasted if you’re hungry.

St. Patrick’s Day – St Patty’s in Boston is a whole different animal. The streets are lined for miles in “Southie” with everyone anxiously anticipating the annual parade. My friends and I pregamed for this parade and then just sat on the stoops as we cheered the paraders on down the road. I had a flight directly in the middle of the St. Patty’s festivities, but def something worth experiencing.

Boston Marathon – Marathon Monday might be the craziest athletic event I’ve ever experienced. When my friend Thomas told me to bring 70s workout gear I was a little confused, but I love dressing up so I didn’t ask too many questions. Apparently, you dress up to encourage the runners and give them something else to look at. Cool.

You also pregame, tailgate, day drink, etc. for this Marathon. Like the Boston Marathon is a city wide holiday, schools are out, streets are closed down…so, drop everything and party.

We smarted at mile 21 and made our way to the finish line. With drinks in hand of course. I encouraged runners by screaming “U-S-A and You Go Girl.” So much fun. I also got hive fives from some really cute military guys. If you plan on running a marathon or know someone running, Boston is the place to do it and that’s no exaggeration.

I hope to make another trip to Boston sometime soon. Have any tips or tricks…please leave me a comment.

1 Comment

  1. September 11, 2018 / 5:19 am

    thank you so much this has given me ideas on an ideal itinerary to put together for my trip – I want to take a week long trip there next year.

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