Traveling for Work

Can it also be for pleasure?

As summer approaches, I look back on my last few summers and think about how I spent many of those weeks away from sunny Long Island because I had to travel to Upstate New York for work. Anyone who knows me will attest to how much I complained about having to do it, but when I was there, I promise I did try and make the best of being there.

When I agreed to travel for my previous job I had imagined it would be trips all around the United States and maybe even international trips every once in a while. Nope. They gave me a bunch of clients in Upstate New York. I was mainly sent up to Poughkeepsie, NY (approx. 3 hours from home) and Ithaca, NY (approx. 5 1/2 hours from home) for client work. We also had to travel a few times for trainings, and those were in different US cities, so at least I got my travel wish for the trainings.

Poughkeepsie was my first out of town client, and it was only for one week, so a week away seemed like fun and it honestly was. I went with a coworker who soon became one of my good friends and who I still talk to almost daily even though I don’t work there anymore. It wasn’t his first time to Poughkeepsie for this specific client, so he showed me all of the delicious local restaurants and some cool spots to see after work at night. After my first fun week there, I found out I would be going back for a few more weeks of work, but this time I wasn’t as excited since it was for five weeks instead of one.

Celebrating my birthday in Ithaca!

Everything sort of snowballed after that. Once other managers saw I was willing to be out of town for one job, I got picked up on a few more jobs that kept me away from home for about 13 weeks total from May – October. If you aren’t from around here, Long Island’s prime season is basically the same exact time, so I was missing valuable summertime with my friends and family. To make it worse, I spent a few of my birthdays away from them too. Luckily, I had amazing coworkers that became friends, and they always made sure I got a birthday celebration! Even though I got to spend this time away with these friends, going away went from being one fun week away to essentially living out of town the entire summer, so I got pretty cranky about it pretty quickly.

Even though I would complain endlessly about going, there were definitely positives about having to travel for work, even if it was just a few hours away from home. I definitely did some exploring after work, and sometimes on the weekends if I drove up early enough on the Sunday before. Here’s a little tidbit about each place I worked from:


Since I spent so much of my time here, I feel like Poughkeepsie, even today, holds a special place in my heart. Maybe the food won me over though, I don’t know. I still miss the restaurants from here; they were always my favorite part of going up there. Another great spot is the walking bridge that offers some amazing sights.  It’s a really relaxing walk in the evening, and a perfect spot to watch the sunset! Any night I was able to sneak out of work early (which to that job meant before 7…gross), I would head over to the bridge for a little stroll. At the bottom of the bridge there are a few restaurants, and one of my favorite spots, Lola’s, is there! My manager from this client still sends me the menu with the daily specials every now and again when he see something we use to regularly get, that is how great this place is. (PS we both don’t even work at that job anymore)


  • Lola’s Cafe
  • The Mill House Brewing Company
  • Rossi’s Deli (the biggest sandwich you’ll ever see in your life)
  • Walkway over the Hudson


Cayuga Lake, NY

Ithaca is probably where I spent the most amount of time after Poughkeepsie. Ithaca is a bit further upstate, so there is a completely different atmosphere up there. Everything is much more relaxed and quiet, and there are many more places to go to participate in some outdoor activities like hiking, kayaking, paddle boarding, etc. There are a bunch of different hiking trails to keep you busy while you’re there. A majority of the hikes are relatively simple and always offer some incredible sites. The first hike I went on up there was not that simple, and it was essentially what I think of as a million steps. I want to say I’m not exaggerating, but I know I am. It really pointed out how badly I needed to work on my stamina! One of my workers and myself laughed at ourselves the entire way through it, while our other two coworkers laughed at us for how badly we were struggling to finish it. That’s a memory from being in Ithaca that I will never forget. After the hike, we went and got a well-deserved dinner in the downtown area, which is flooded with a bunch of yummy spots to go to. If you want to stray from the downtown area for dinner, I recommend making your way to Ithaca Beer Co, which is the local brewery there. The food is delicious, and the beers are even better! This brewery is where I discovered my love for sour and fruit beers.


  • Hiking Trails/Gorges
  • Ithaca Beer Co.
  • Downtown Area – restaurants galore!
  • Gorger’s subs (and Gorger’s tacos – RIP)


Boston Cream Pie; Omni Parker House

I went to Boston for my very first week ever at my old job. It was where they were holding the training that year, and I was beyond excited. I had been to Boston once before and absolutely adored it. Being it was the first week of the job, it was also the first time meeting some of my future coworkers that week, and we got to make great memories together right away. One of my favorite memories from this little trip is remembering my first ever Boston Cream Pie IN Boston at the place of origin of the pie, The Omni Parker House (originally it was called “Boston’s Parker House”). It might have been one of the most delicious desserts I had ever eaten in my life, and I cannot even explain why I waited until I was 21 to try it. I’ve been to Boston for both work and pleasure, but since this post is about work related trips, my highlights in this post will only focus on things I did/places I went during work.


  • Omni Parker House (and did I mention it’s haunted for all your horror lovers out there)
  • Museum of Science
  • Faneuil Hall Marketplace


St. Charles, Illinois

Our annual training was held outside of Chicago in a city called St. Charles, but we always would just say we were going to Chicago because it was just easier than to explain where St. Charles was to everyone who asked. Every once in a while a few coworkers would get together and organize a little trip to the real Chicago for a few days before the training in St. Charles. There is no better way to get to know your coworkers than to be on a trip with them especially since the first few days of the trip were technically not for work. Like I said, we went on these trainings annually and it was usually with the people we started with, so you tend to go with the same group of people every year, and it gets better every single year. When we went to Chicago for the last training we all went to together we got an early, early morning flight in and took advantage of every second we had there. Downtown Chicago has endless restaurant options, and I would love to recommend the place we went for brunch, but to be quite honest I don’t remember what it was called because the mimosas there were THAT good. I think I do remember them not being bottomless, but we didn’t let that stop us! I’ll have to do my research and come back around to that another time. After that we went bar hopping around town and had an absolute blast just making the best of being there all together even though we knew it was technically because of our training in a few days. We also took our opportunity to get to a Cubs game at Wrigley Field, which is a must-do!


  • Wrigley Field & Wrigleyville
  • ACME hotel (the décor here is incredible)
  • Rock Bottom Restaurant & Brewery (great rooftop bar!)
  • Giordano’s Pizza
Wrigley Field with some of the best coworkers turned friends I could have asked for!

So can travel for work also be for pleasure? The simple answer to that is yes, but of course it will only be a enjoyable as you let it be, so focus on having the best attitude possible if you’re in a situation where you’re being sent somewhere you really didn’t want to go like I was. Every town/city, no matter how far or how close, can teach you things you’d never learn from your hometown. You might try a new food, see some local art, see a new animal that you don’t have in your local area, literally anything can happen when you open your eyes and just give it the chance. I cannot deny the fact that I complained way more than I should have about traveling for work, but looking back, I am happy that I did and have learned to appreciate any form of travel. I do have to say, I am extremely happy to not have to travel for work anymore because it makes personal travel that much more exciting, but I am grateful for the experiences I had and I will always cherish the memories I made with the people I got to spend that time with!

Do you ever travel for work? Where do you go? >> Comment below!

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