Power Trip: What to do in Boston (when you’re stuck on a work trip)

What to do in Boston? Visit the Boston Public Library on a partly-cloudy day.

As a career girl whose goal is to travel the world with a full time job, opportunities to travel can be limited to my paid holidays, vacation days, and personal days.

It’s not like it’s my job to get paid to travel.

Until it is. My employer asked me to attend a conference for work [cue victory dance]. The destination: Boston.

My top priority was work. That was my number one commitment. But I still made it a priority to experience the city, so I did my best to figure out where to eat in Boston and what to do in Boston with limited time while on a work trip.

Here are a few tricks to maximize your work travel to incorporate some fun travel:

Arrive earlier. The early bird gets the worm. If you really want to take some extra time to explore the local area, plan to arrive at the earliest convenience. For this particular trip, I needed to start working in at 2pm on Sunday. I woke up at 3:30 am that day to catch a 6:30 flight to land at 8:15. Five hours was plenty of time to get breakfast at Flour Bakery + Cafe, stroll around the Public Garden, visit Boston Common, and begin walking along the Freedom Trail.

Leave later. Rather than turn and burn after the last session of the conference, I planned a late night flight home so I could spend the afternoon exploring. Was it a late night? Yes. Was I exhausted at work the next day? Slightly. Was I glad I got to tour around Boston on a trolley and indulge in the best lobstah rolls in town? You bet.

Find out where the party’s at. I quickly learned that several companies sponsor parties to entertain clients, impress prospects, and network with attendees. Though I didn’t have any invites prior to the conference, a few conversations on the exhibitor floor led to more information and list of invitations. Because of these parties, I was able to visit Fenway Park, Cheers, and House of Blues. At no charge!

Plan meetings offsite. Have an important meeting? Rather than meet at the convention center coffee shop or meeting space, suggest meeting at a local restaurant – you know, a place that you really really want to eat at. Lucky me, I got to eat at an amazing Italian restaurant in the North End for a business meeting.

For an in-depth dissection of how to maximize business travel for fun travel, read: Desk Departure Tip: make personal travel an extension of business travel.

I’m still amazed at the amount of things I was able to do in Boston during my 3 night stay, but when I calculate the amount of “free time” granted after the work day and industry parties, I had saved up a solid 16 hours of free personal travel time.

Here’s what I managed to do in Boston

Where to Eat in Boston (when you’re stuck on a work trip)


Flour Bakery + Cafe

Approximately 30-45 minutes.

When searching “best breakfast in Boston,” Flour popped up on several lists. This place was packed. I was lucky to get a seat, as much of the place was standing room only. It really isn’t a sit down restaurant. You wait in line, order at the front, and wait until your name is called to pick up your order. I tried the breakfast sandwich and oh. my. goodness. Can I get a Flour in Detroit? The all natural egg square was so light and fluffy (almost buttery), the bacon was thick and crispy, the hollandaise sauce added a vinegary zing, and the bread was carbolicious.

Italian Restaurant

Approximately 1.5 hours.

The North End of Boston is home to some of the most incredible authentic Italian ristorantes, gelaterias, and cucinas. If you’ve ever indulged on the culinary delights of Italy in Italy, your tastebuds will think you’re back in the fatherland.


Neptune Oyster

Approximately 1.5 hours (if you’re not dining at peak times)

I made a promise to myself that I would save my first lobster roll for New England. And because I couldn’t just eat my first lobster roll at any corner store, I did my Google research of “best lobster roll in Boston” and sure enough, Neptune Oyster came fiercely recommended. In fact, according to the internet, don’t bother to waste your time anywhere else. So I made the hike and waited 30 minutes at 1:30 pm on a Wednesday – it’s that busy and that popular. The space is small and narrow, with only a few tables and a long bar. This lobster roll changed my life.

What to Do in Boston (when you’re stuck on a work trip)

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Walk in the Public Garden and Boston Common.

Approximately 1.5 hours.

Both the Public Garden and Boston Common share the title of “first in America” for public botanical garden and public park, respectively. Boston is considered to be one of America’s most walkable cities, and that becomes apparent when you stroll through the centuries old paths.


Meander along the Freedom Trail.

Approximately 1 hour.

Purchase tickets for a guided tour, or walk yourself by following the red bricked line. The Freedom Trail is a 2.5 mile track that cuts around Boston along historically significant sites. It begins in Boston Common near the Visitor’s Center; this is a sensible transition from my previous suggestion.


Visit Fenway & have a drink at Bleacher Bar.

Approximately 2 hours.

Sports tourism isn’t my niche, nor do I have much interest in athletics, but I care about history and what is unique and important to the local area. Fenway Park is one of those places. Fenway Park is listed on the National Registrar of Historic Places because of it’s deep roots with American sports and famous American athletes (think Babe Ruth). Baseball is America’s pasttime, and Fenway is one of the remaining stadiums from the golden age of baseball. Not interested in visiting for game? Drop in for a drink at Bleacher Bar, where you’re nearly inside the stadium.


Say cheers at Cheers

Approximately 1 hour.

Confession: I’ve never seen Cheers. I have no idea what the premise of the show is, but I guess it’s one of those “American Classics” like Seinfeld and Friends (neither of which I’ve seen – strike 3?). Regardless, it was a fun time.



Take a Trolley Tour.

Approximately 5 hours.

Yes, it’s a hefty $40 and yes, some of the drivers are ridiculously corny, but hop-on-hop-off Old Trolley Tours easily pay for itself with the convenience of transport, historical narration, and simple way to orient oneself in a strange new city.

If you were to sit on the trolley and never get off, the entire trip would take about 2 hours and 15 minutes. Since my time was limited (only about 5 hours of free time), here were my favorite quick stops:

Massachusetts Institute of Technology


Beacon Hill & Acorn Street

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North End (home of Neptune & Italian deliciousness)

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Trinity Church & Boston Public Library

This place is amazing. I recommend spending as much time here as possible.

This place is amazing. I recommend spending as much time here as possible.

If you have a work trip to Boston, lucky you. Whether you’re there for a few days or only have a few hours to spare, I hope these suggestions on what to eat and what to do in Boston serve as a work trip guide to maximize your time in Beantown.

Here’s a Google Map of all the places mentioned in this post!

Don’t forget to pin it!

what to do in Boston

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