5 Weeks, 19 Cities, 1 Significant Other: Life on the road with your partner

We are so excited to have our friend Shelby Leeman as our guest writer today! She is sharing her experience of road tripping across the country with her significant other and telling us all how to survive, I mean, ENJOY doing the same! 

5 Weeks 19 Cities 1 Significant Other: Life on the road with your partner


Life on the road with your partner

After 3.5 years at the White House, I was ready for a bit of adventure. Originally I imagined lounging on Caribbean beaches, drinking pina coladas with my boyfriend. But after a month of listening to his sound arguments, our plans changed as we agreed to road trip across the country together. The trip was open ended - a flexible schedule, general travel guide, mix of sleeping arrangements with absolutely no bookings (a stipulation set by my partner in crime). While I appreciated the idea of opening ourselves up to adventure and whimsy, the idea of driving across the country with no predetermined locations to sleep did generate some anxiety. Thankfully, my partner understood my reservations but insisted I push my boundaries. Trusting him, I was willing to compromise and agreed to no bookings but developed a loose (although flexible) model for the trip. What started as a condition ultimately became the best element of our trip. It necessitated strong communication and teamwork as well as provided us the opportunity to breathe, explore to our hours content and discover gems like the spa town of Truth or Consequences, NM. 

Life on the road with your partner is amazing but comes with some unique challenges. Here are a few tips to consider when planning a trip with your significant other.

how to plan a trip with your partner

Set a budget and follow it 

Money can be a huge strain on any relationship. Avoid problems by setting a budget and sticking to it! While we were flexible with our time, we were not regarding our budget. Recommendation - Use the Google Sheet app on your phone and track spending. Knowing how much money you’ve used and in what areas (I used general categories such as food, hotels, gas, activities, and other), enables you to shift spending to reduce costs or figure out when it is time to go home. 

Stay Active 

Neither my boyfriend or I had been west of the east coast before this year. As a result, we were interested in observing the differences in scenery throughout the country and secretly shopping for our future home. Early on we purchased an America The Beautiful Pass, which provided us with access to all National Parks and Federal Recreation Lands. From that point on we were able to hike in any National park without paying admittance. This not only saved us money but provided the opportunity to absorb the beautiful land (forever changing as you drive from East to West) and burn off energy ensuring a sound night's sleep. 

Visit New Places

Include locations on your trip that neither of you have been. You can create new memories in these locations together and enjoy the amazement hand in hand. 

Expect Hiccups and Be Flexible

When traveling nothing will ever go perfectly. For us, one such moment occurred during the drive from Truth or Consequences, NM to Tucson, AZ. Needing to burn a few hours in the middle of the day, we decided to visit Chiricahua National Monument as it was only a short bit out of the way. We plugged the location into google maps and were on the road again. What we didn’t realize (as we continued to find ourselves more and more isolated) was Google's shortest route took us to Apache Pass Road, consisting of approximately 10 miles of dirt road through hilly territory. Now, depending on your vehicle this may be no big deal but we were driving a KIA Optima which is not intended for vigorous terrain. With no cell phone service my boyfriend dredged on down the road; my anxiety rose in proportion to his genuine excitement. We were fortunate that nothing went wrong but we made the most of the situation at hand and made sure we snapped a few photos once safely on the other side. 

How to plan a trip as a couple


An obvious point but a necessary one. Compromise! Your trip is for both parties in your relationship. Each of you will have different desires for your experience and both need to be met. Chose a combination from both wish lists and enjoy the adventure that comes along with each opportunity.

Pick a Playlist and/or Podcast Together

When road-tripping you have to expect hours to be spent in the car with your significant other. While we managed to limit our driving stints to 8 hour maximums, we still needed some entertainment for the rides. We decided to fill a portion of the time with music and podcasts. Branching off of my last point, this is all about compromise. My boyfriend and I have polar opposite taste in almost all things, so we chose a combination of our preferred selections. 

  • Him: The Talking Heads, Kanye West, The Tim Ferriss Show, and Malcolm Gladwell

  • Her: Halsey, Gregory Alan Isakov, Tove Lo, and The Black Tapes

While I know he did not enjoy the Black Tapes (nor I Malcolm Gladwell) at all times, we listened, laughed and talked about each episode or jammed out together.

Enjoy the Silence

Every moment does not need to be filled with noise. Sometimes the best thing you can do is sit and absorb the world around you.

Many thought we were crazy, destining our trip and relationship for failure but we flourished on the road. The trip enabled us to not only see the country but to learn new facts about the other and share our dreams together. We’ve continued to apply these tips in our relationship, enabling us to successfully work together personally and professionally for the last year (yes, we now work together full time). After 6 years of dating, we love each other more today and are confident of the life we intend to build together. Our vacation was so much more than that, it was a blessing for us individually as well as for our relationship. I’m lucky to say that in 2017 I spent 5 weeks on the road, visiting 19 cities with the love of my life and walked away with much more than a handful of amazing stories to tell. 

Planning a trip with your partner? Read this first!

PaperFinch Travel TIP: Start by planning your homes away from home here.

5 Weeks 19 Cities 1 Significant Other: Life on the road with your partner
Shelby Leeman is a freelance Photo Editor and Color Specialist based in Charlotte, NC. Prior to freelancing, Shelby worked in the White House Photo Office as the Digital Imaging Specialist where she post processed, distributed and printed images documenting the Obama administration. Leeman received her BS from Rochester Institute of Technology in 2012 after studying Biomedical Photographic Communications. Recent accomplishments include color correction for images in Pete Souza’s book, Obama: An Intimate Portrait and Amanda Lucidon’s book, Chasing Light: Michelle Obama through the Lens of a White House Photographer.


Find Shelby on the web: www.shelbyleeman.com | Instagram  @shelbyleeman