Boston (Work Trip) Guide

To the Interested Traveler,

Lobster rolls, Red Sox, Beacon Hill, Tom Brady…that’s right I’m talking about BOSTON! Last week, I spent a whopping 24 hours in one of the most historical cities in the United States for a work trip. It was my first ever overnight work trip, so getting to travel to a city that I had been to before and loved was already so great and of course I had all the lobster on my mind.

My whole purpose here is to try to be as helpful as I can, and even though my trip was short, it was JAM packed, so I thought I could be a trusted resource by breaking down how I packed for a 24-hour work trip and the cool places we went while in Boston. All you newer professionals or world travelers out there, I hope this can spark some ideas for your next trip to Beantown.

Where I Stayed:

We were a little concerned about where our hotel would be situated in the city because if you’ve ever been to Boston before, you know it’s a spread-out city. But the Marriott Long Wharf was perfect. Not only did it back right up to the harbor, which boasted amazing views of the water, it is also located far enough in the city where it’s not as crowded but still provides a great pathway to shops and cool sites to see. The hotel is newly renovated, super clean and has one of the best hotel restaurants to sit and have lunch. I had an Acorn Squash and Goat Cheese salad with Salmon, and it was to die for. Also, one of the best sleeps I’ve ever had in one of the most comfortable beds I’ve ever slept on. Is it weird that I was off put by the front desk associate calling me Miss Thompson the whole trip? Lol

Where I Ate:

As mentioned above, we started with lunch at the Waterline restaurant, which is right inside the Marriott Long Wharf hotel. This would be a great spot to grab a drink before heading to dinner too because the bar in the restaurant is hugeeeeee. For dinner, we went to one of the premier steakhouses in the city called Grill 23. As soon as you walk in, you get that historical, old-timey, wood encrusted, grand staircase, classic vibe. I chose from the ample wine menu at the bar area, which is a popular Happy Hour spot, before being seated upstairs. For our meal, we did a little bit of everything. The sides and apps are meant to be shared family style so you can try many different options. My favorites of the night were my Halibut entrée which came with steamed mussels and the Lobster Mac n Cheese.

Where I Grabbed a Drink:

After dinner, we knew we only had a few more hours in the city, so we decided to grab a drink before bed somewhere close to the hotel. A local Bostonian referred us to the Envoy Hotel, which they claimed has the best skyline views of the whole city. Let me tell you, they were no lying as you can see from the first picture above! The hotel itself was very sleek and contemporary and then you go up an elevator to the trendy rooftop cocktail lounge. Great music and great drinks. It was such a cool spot to look past the Fort Point Channel right into the city.

What I Packed:

When I was packing for such a short work trip, I wanted to keep two things in mind – pack light but pack with intention. I’m the type of person that needs to have options, so I packed very strategically with five staple work pieces that could all be paired differently with one another: A blazer , a black work-appropriate dress, classic blue jeans, black trousers and a printed blouse.

All the combinations I could have worn with those pieces:

  • Blazer with dress
  • Blazer with blouse and jeans
  • Blazer with blouse and trousers
  • Blouse and trousers
  • Blouse with jeans
  • Just dress by itself

 One pair of Mark Fisher heels and that was it. I packed everything in a small, carry-on sized suitcase so I didn’t have to worry about the hassle of checking a bag. I would say, as a habitual over packer, I did pretty great for my first ever work trip.

This is a very random note to end on, but as this was my first work trip, I was very hypersensitive to my surroundings. I usually don’t fly with airlines that have a First Class section, but this one did. I noticed both flying to Boston and back home, the only type of person sitting in First Class were men, and men you could tell were traveling for business. I don’t know why this bothered me so much, but it made me think of how representative that is to what we are seeing in society every day. We need to get some more women up there enjoying luxury 30,000 feet in the air. Just some food for thought. All in all, Boston was amazing and I definitely need to go back for fun soon!


2 thoughts on “Boston (Work Trip) Guide

Leave a Reply