Traveling with a Travel Blogger: An Exercise in Waking Up

Have you ever wondered what it would be like to travel with a travel blogger?  Because I’m going to be honest–it is a different travel experience.  And while many travel bloggers–myself included–have attempted to write about how travel blogging changes travel, we may not have accurately captured the essence of a travel-blogger trip.  It is often hard to describe an experience from the inside; the best perspective is often that of an outsider. 

Thus, I’m so happy to be able to offer you The Suitcase Scholar’s first-ever guest post–the true story of what it is like to travel with a travel blogger, told from the point of view of a non-travel-blogger.  Because I’m super OCD, I will occasionally jump in with my own thoughts [brought to you in bracketed, red print].  But for now, take it away, Dustin…

Traveling with a Travel Blogger:  An Exercise in Waking Up

written by Dustin Dreese

As the personally nightmarish year of 2012 came to a close for me, I vividly remember sitting on my couch thinking about the next chapter of my life.  That evening, my long time and recently rediscovered friend Tracy sent me a text message.  She asked if I had plans for the end of the year, and explained that she was trying to fit one last trip in before the New Year–and that she wanted me to go with her.

It seemed I had two choices.  I could take an inexpensive trip to a new city where we would spend our time taking educational tours, exploring the food and drink culture, and meeting new and interesting people.  Or I could spend the weekend sitting on the couch trying to figure out my life.  Oddly enough I think it took about 48 hours for me to say yes.

The Carnegie Museum rocks! Get it? Rocks? Ha…ha? Ok sorry. (Note: Tracy wrote this cheesy caption).

In the years we lost touch, Tracy apparently managed to build up quite a resume.  She worked for the Environmental Protection Agency (which coincidentally I learned was because they had fastest internet service she had ever used in the early 2000’s), decided to become a teacher, became disenchanted with the current state of the public education system, and then decided to try and make a living doing what she loved more than anything: traveling.  If what I wanted more than anything was to revitalize my spirit and break the stagnancy, spending a long weekend with someone like Tracy would certainly offer that opportunity.

[Tracy interjects:  I’m really not as awesome as Dustin makes me sound.  Not even a little bit.]

In what I can only assume was a preemptive strike against possible conflict, Tracy was very upfront about what the trip would look like.  She explained that as a travel blogger, she needed to maintain a schedule, that the tourism board hosting her needed a return on their investment, and that she would make sure to plan a lot of pit stops for booze.

A note about me: I’m completely uninterested in creating agendas or plans for a vacation.  Typically I’m a “go where the wind blows you” kind of guy.  A few years ago, my husband and I vacationed in Walt Disney World.  While I was excited to see the castle for the first time since I was 8, he was excited to see every single thing the park had to offer.  He created a color-coded spreadsheet with icons specifically for each park. [Tracy interjects: sounds like the perfect way to plan a Disney trip!]  Every day was planned and charted, and while I had one section on that spreadsheet marked “Dustin’s Day,” it was really just a two hour period for me to sleep in.  So, while timelines and schedules aren’t something that I gravitate towards on a vacation, it’s not a foreign concept for me.  My point?  I was prepared for a regimented schedule.

Dustin and his husband in Disney’s Animal Kingdom.

Wandering the streets of downtown Pittsburgh. We totally were not lost. We swear.

In the days leading up to our adventure, I received almost daily email updates from Tracy about the progress of our travel arrangements.  She explained her process, beginning with contacting travel bureaus, individual attractions, hotels, and other tourist organizations to let them know she would be visiting their city and writing an article about her experience. Within an hour she started to receive responses from the city regarding activity ideas and lodging options.  An hour later she wrote to let me know that she had arranged a stay in the Omni William Penn Hotel in downtown Pittsburgh.  I was surprised how quickly she was able to set up these important elements of our trip, as well as how positively she was received by the city of Pittsburgh. [Tracy interjects: this almost never happens.  The lovely people at Visit Pittsburgh and at the Omni William Penn were some of the most helpful people I’ve ever had the pleasure of working with.] Within a week she had planned out each day with well researched and exciting activities that would allow us to leave Pittsburgh feeling like explorers.  Needless to say, I was excited.

One week later, as I was driving the hilly highways that spanned what seemed to be the middle of nowhere, I rounded a curve to a surprising view of the entire city.  Pittsburgh is nestled in western Pennsylvania’s countryside, almost hidden until you’re on top of it.  You can almost smell the history as you approach.  Once in the city, it’s east to get a little rattled.  The roads are the antithesis of a grid system, which is actually something that I grew to appreciate.  The city’s design basically means that wherever you stand in it, you feel depth.  The buildings aren’t lined up neatly like in New York or Chicago; they are askew.  This seemingly unplanned urban design creates a feeling of comfort and coziness that I haven’t experienced in other cities.

After I made my way through the dense, winding, and picturesque city streets to the Omni William Penn Hotel, I was immediately impressed with the accommodations Tracy had arranged.  The hotel was, in a word, grand.  Decorated beautifully for the Christmas season, the lobby was wonderfully ornate, bustling with travelers.  A giant gingerbread replica of the hotel was displayed across from a floor-to-ceiling enormous Christmas tree.   One wouldn’t necessarily think of Pittsburgh as an invigorating city, but I felt the energy and it was fantastic.

[Tracy interjects:  Pittsburgh is freaking awesome. Click that link to find out more!]

After a warm hug and after settling into our room, we decided to walk to a sushi restaurant for dinner.  We needed to go over our plan for the next few days.  Tracy put together a list of must-see attractions–museums, restaurants, historic landmarks, etc.  She again reminded me that while we would be having plenty of fun, we did have a purpose and a responsibility to the city.  I was ready to contribute in any way I could.

We call this photo ‘handsome, with a sandwich’. Dining at the Market Square Primanti Brothers.

The next morning we woke up, got ready, and went out the door to start exploring.  It was weird for me to have an actual purpose on a trip like this.  I mean, I’ve been on many trips, and while relaxation and decompression were on the agenda, a purpose was quite another feeling.  It actually made me more energized and ready to experience things, not just observe them.  Having just come off a long stint of being an observer of life, having a purpose was a welcome feeling.

At first, Tracy seemed almost apologetic about how much she wanted to accomplish, and she checked in frequently to make sure I wasn’t annoyed by our task and schedule.  After a few rounds of reassurance and after explaining that I was here to help, we fell into what I can only describe as a “groove.”  We went from attraction to attraction, soaking in the educational wonderfulness, laughing and talking as we explored Pittsburgh.  I would drive, Tracy would take photographs.  We talked with people we met about the history of the city, and both of us would discuss topics to write about and the angle from which to write them.  I would look up walking directions on my phone and then we would get lost anyway.

One of the many things I noticed about Tracy was her discipline.  She would take notes on her iPhone every place that we went.  A lot of notes.  Had she told me about this process before I went I would have been preparing to have broken and interrupted interactions for the whole trip.  However, most of the time it was so fluid and quick that it just felt like a natural reflex for her.

In addition, she developed a great eye for photography.  I’m one of those people who loves having an expensive camera, but when push comes to shove I find myself thinking shit, why didn’t I take a picture of that while I had the chance?  But Tracy would stop in mid conversation to snap a walking photograph and then quickly re-enter the conversation as if nothing happened.  She was the very definition of a multi-tasker and I was impressed by the process she developed.

Tracy interjects with a caption: Dustin was making fun of me for taking photos of everything. And then I caught him doing the same. So of course I took a few photos of that!

My point is: it was easy.  Relaxed.  My time with a travel blogger reminded me, in a wonderful way, what travel is all about.  It’s not about going somewhere new, eating the food, seeing the sights, and then leaving.  It is about connections.  It’s about taking an experience and letting it alter your perception of the world–something that is scary for most people.  Something that, until you’re reminded how much beauty these kind of connections add to your life, you unfortunately are content without.  Or so you think.

I am so happy that I reconnected with Tracy and I am so happy that she is a travel blogger. [Tracy interjects:  So am I.  On both counts.]  I am proud of her for doing amazing things with her life, and while I know she is tough on herself and uncertain about the path she walks, she is an inspiration.  She served as a loud reminder to me that while life can beat the shit out of you, life can revitalize you as well.

I am more observant because of my time with a travel blogger.  I am more motivated because of my time with a travel blogger.  And perhaps most exciting, I am more awake because of my time with a travel blogger.  And so, I give a heartfelt thank you to my wonderful friend Tracy, and the fantastic city of Pittsburgh.

[Tracy interjects:  I love you, Dustin.  You are a fabulous travel blogging companion.  Where shall we go next?]

I asked Dustin to write this post before we even arrived in Pittsburgh.  I thought it would end up being a post about how miserable he was traveling with me on a blog trip.  Clearly, he was not miserable.  He sent me this post on Valentines Day.  It was, without a doubt, the best valentine I ever received.  Thanks, Dustin–for this post and for a wonderful long weekend.  Oh–and even more thanks for driving me around snowy Pittsburgh in your awesome car with heated seats (and the GPS you occasionally ignored).