9,013 Miles

Four life long friends just graduated college. What was next? Straight to the real world? No, how about a four week journey from Boston, MA to Portland, OR and back.

After two years of talk and little planning until about a week before we left, I am here to tell you it is possible. I've put together a few tips that worked well for us as well as some ideas for how you can possibly make your experience better... but we had a pretty amazing time, so that's a challenge.

1. Map out your route.

People often advise against making too many plans before a road trip, but the plan we set did a good job of moving us forward when there were plenty of distractions to set us back. This is not to say you have to plan everything down to the minute, but when you have a set timeframe, a day-by-day plan can help keep you moving along. We booked out where we were staying every night all the way to Portland, so we had no option to stay longer unless we wanted to forfeit our funds to the Airbnb/hotels.

As far as the activities we did in each spot, we put together a list of possibilities before and usually decided how we would approach them the day of or a day before.

2. Budget

This may seem obvious, but it very important for everyone to be on the same budget so there isn't one person holding the group back from doing something. You don't have to do everything together, but it helps to put together a rough idea of what you will be spending money on throughout the trip. There are plenty of apps that can help budget for gas, (Roadtrippers, Mapquest, etc.) which was one of our major costs. We found it was easiest to do a rotation of who was filling up the tank. If you book out most of your lodging before heading out, you'll have a better idea of what you can spend on tours, food, tickets, and so on.

Now I would advise spending your money on experiences rather than tangible goods. I bought a few hats and a sweatshirt, but I found some of my friend's purchases to be a bit wasteful. You are, after all, doing the trip for the experience of seeing as much of the country as possible... but to each their own. I guess I'll never know what it's like to wear cowboy boots to a Cardinals game, oh well.

3. Have a theme.

This might be the most important emphasis before hitting the road. Make sure that everyone is on the same page for what they want to get out of the trip. For me, I wanted to focus on taking photos and video, doing as much hiking as possible, and trying new and interesting foods. We started off the trip with a lot more drinking than I expected, and obviously that was not a cheap expense. This being said, the first half of the trip was more city based so I expected a few drunken nights (Nashville, $1 beer night at Churchill Downs), and once we got out West, the attention shifted toward hiking and seeing natural scenes.

4. Have a good group of friends.

I could not imagine doing this trip by myself. Having grown up with these guys made the long rides much easier than anticipated. We were quick to develop some inside jokes and our delirious minds kept the mood light (and the driver awake).

Being with any group of people 24/7 for 28 days isn't going to be all sunshine and flowers so expect to get into a few scuffles/arguments, but know the people you are with. There has to be someone who can level everyone out when tempers flare. You have to expect a couple of these, but that brings me to my next point.

5. Be Flexible.

Now, you will probably see this in any road trip guide, but it is VERY important and will lead to a much more relaxed and enjoyable trip. Many of the arguments we had during the trip were due to people having their own agendas and not being willing to wait or just go with the flow. I was guilty of this early on when we were having late nights drinking and getting up later in the morning than I wanted. As we moved on, I learned to let these small things go and in turn, I began to relax a bit more and live in the moment. I was traveling across the country at 22. How many other people can say they have done that in their lifetime?!?

A few nights we ended up sleeping in the car, which, for four relatively tall guys, wasn't the most comfortable night's sleep, but it didn't cost us anything. Sometimes you just have to sacrifice a night.

6. Reach out to family, friends, strangers...

One way we were able to cut some costs was by reaching out to people in the areas we were visiting to see if we could sleep on their floors for a night or two. This added up to about 10 nights of free lodging plus 2 nights sleeping in the car, so about 1/3 of the trip we were not spending money to sleep. Often, people think direct relatives or friends, but ask around. See if anyone knows anyone. We ended up getting a place to stay from my grandmother's friend in Louisville right next to where my mother grew up.

7. Journal/Camera (form of documentation)

This trip is going to be an unreal experience! You are going to want to remember every part that you can of it. The four of us were regularly updating our journals with the events of our days and the funny stories or jokes that we were telling each other. Looking back on the entries, it is wild to me how vivid the memories are.

Having a camera to me was very important to look back on the memories with a visual reminder, but one of my friends found it important to truly live in the moment with few distractions. He just brought a film camera with a couple rolls so he was limited to pictures that brought some strong meaning to him. It is all a matter of preference, but I think it is cool to be able to share my pictures with everyone and tell my story that way. (Check out my Instagram for more pictures and videos).

This is a must!!! 8 hours in the car can get brutal. Make sure you have PLENTY of playlists with ranging genres. There is nothing worse than listening to the same song 20+ times in 2 days. Podcasts are great as well and comedy is extremely important. Many of our jokes were those based off the stand-up that we listened to in the car.

Our final drive from Chicago to Hull, MA was 17 hours. I started driving at 6 PM and ended around 3 or 4 AM. How did I do this you ask? I had the best DJ in the ENTIRE WORLD sitting next to me playing the absolute best lineup of songs I have ever heard in my entire life. If that doesn't scream the importance of this tip, I don't know what does.

Hope this helps and I wish you the best on your next trip! It is one of the best things anyone can do for themselves.