Road Warrior: My Top 5 Favorite Places to Travel to For Work

Posted by
person holding smartphone riding airplane
Photo by Jason Toevs on

Being in sales, it is very important for me to travel so I can meet prospects, partners, and clients face-to-face. This is true for a number of reasons. First and foremost, trust is built (both ways) the more you actually get to know people. Too much is left to the imagination about someone else’s personality if all interactions are handled digitally. You cannot read their body language, a key indicator into how someone is really feeling about a thought or idea. Second, more gets done this way. People just take meetings more seriously when they are staring across from someone rather than sitting in a WebEx. Lastly, it shows a commitment to travel to see people and shows them that you value their business and their time. I genuinely enjoy getting to know the people I talk to and actually would say it is my favorite part of my job.


Over the course of my nearly ten years of being in sales, I have traveled to many different places and have been fortunate to see a lot of the country (and the world). Work is work, but there is still something exciting about traveling and being able to take advantage of seeing other places. For example, as I write this, I am en route to Salt Lake City for work meetings with my boss. The next day, we are taking a day off to go skiing. Sometimes, I am fortunate enough to be in a different city when one of my beloved Boston sports teams is playing there – like when I saw the Patriots play in New Orleans or the Bruins play in Toronto. And yet other times, I get to just be a tourist.


Work travel has taken me to many places, and some of the largest city in the US, like Los Angeles, San Francisco, Dallas, Chicago, Miami, Philadelphia, Washington DC, Boston, and New York City. It has also taken me to places I would not have expected to visit otherwise, like Overland Park (Kansas), Tulsa, Birmingham, and Little Rock. No matter where it is, it’s not always as glamorous as I want it to be, and it can be exhausting. And reflecting upon all of these places I have been to, I decided it would be fun to build a top 5 list of places I love to go to for work.



  1. Louisville


I only have got to go here once, but it was a really good time. There is something about being from the northeast and going somewhere where the people are infinitely friendlier that just sticks with you. I really love the whole history here and the racing aspect, and there is a really fun downtown area where everybody hangs out – kind of like a miniature version of Bourbon Street. I’d really love to have an excuse to come back here someday.



  1. Boston


I love visiting Boston because it’s where I come from. It’s also an easy trip for me to make from New York City. But there’s no doubt that I love getting a chance to see my family and friends. Couple that with the possibility of seeing some of the hometown sports teams in action, and I get even more excited.


Even though I am a homer, I would still say Boston has a lot to offer any traveler. There is a lot of history in Boston, and so many things to do for someone with some time to kill. Unlike in NYC, it’s actually kind of doable to get a good understanding of what the different neighborhoods are like in Boston in a very short period of time. Whether it’s in the historically Italian North End, the Theater District, or the more upscale Back Bay with its infamous Newbury Street, there is a lot to do in town without feeling utterly overwhelmed.



  1. New Orleans


New Orleans is just my favorite city in the United States, period. I love New Orleans for these (non-exhaustive) reasons:


  • It has an intangible character to it.
  • Its people are truly awesome and I love how passionate they are about their Saints.
  • The food is just the best there is to have. You cannot beat Cajun in NOLA.
  • Awesome live music almost anywhere you want to go.
  • It is very affordable.
  • They let you carry a drink on the street!
  • Bourbon Street is one-of-a-kind, even if it kind of smells like urine and just looking at it gives me a headache.
  • There’s no shortage of fun things to do here, and even getting out to the bayou is pretty cool to see some gators.



  1. Miami


Sunshine, happy people, Cuban food. These are three of my favorite things. Need I say more?



  1. Las Vegas


This is probably a polarizing choice, but it has to be my number one. I meet people from time to time who say they hate going to Las Vegas for work (or otherwise). These people must be the most unpleasant, boring, fun-hating human beings on earth. Let me explain why.


Vegas has offered me different joys in different times of my life. When I was younger, it was more the partying scene that attracted me. As I have gotten a little bit older, I still dabble with the parties from time to time, but it’s really about a lot more. The best of everything is at your fingertips in Vegas – much like it is in NYC – but with much better weather and happier people. There is an eclectic variety of some of the finest restaurants you can possibly visit and also the best fast food, right next door to one another. You could literally eat steak at a five star restaurant and then walk across the street to an In ‘N Out Burger. There are all sorts of ridiculously talented people performing stand-up comedy, Cirque du Soleil, or magic. It is the capital of entertainment. Which means you need to hate being entertained to hate Vegas.


You can go to the pool. You can have the most lavish brunch buffet in your life. You can gamble. You can gamble on sports! You can go to the spa. You can go to the Grand Canyon. You can ride in a helicopter over the strip. Seriously, if you cannot find something you like to do in Vegas, you do not like doing things, in general.


The people who rip Vegas often do so because they think it is sleazy or smells like cigarettes. I have news for those people: you don’t need to stay at the Excalibur. If you complain so much like a Yelp reviewer, then you can fork over the money to stay somewhere nicer where you do not need to deal with the stuff you do not like, such as the smell of cigarettes, or even a resort that has a casino. I personally find the gambling to be exciting (in moderation), but there are many family-oriented resorts without casinos that have great pools and other places to relax and not be a complaining little Grinch who hates fun or the mere idea of other people having fun.




So that’s the top 5. Let the debate begin. Maybe the next blog, we’ll cover the Bottom 5.

Leave a Reply

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s