6 Ways To Guarantee An Awesome Road Trip


“Nothing behind me, everything ahead of me, as is ever so on the road.” – Jack Kerouac.

1. Have Good Company.

This one is a no-brainer. Any group can go on a road trip together but the successful ones are the ones who mesh well before the trip. If you’re going to be spending a lot of time in close quarters with each other it’s certainly a good start if you all know and like each other to begin with.

2. Have a Plan.

I’m a fan of the 24-48 hour rule in terms of plans. Have a general idea of where your life is going to take you in the next one to two days but don’t overthink it. Also it’s a safe bet to know generally how you’re going to get to your destination. If you’re heading out east to New York and you’re enjoying watching the sunset in front of you every night then you may have made a mistake or two. Do a little bit of research, find out where are some cool and safe places to stay the night and do some exploring.

3. But Not Too Much of a Plan.

With that said don’t gnat’s ass your entire adventure down to the minute. I know some people are super organized and need to have every little detail planned well in advance but let’s be reasonable here. A road trip is about adventure and excitement and venturing out like Kerouac into the unknown is a wonderful and wondrous part of life we should all be grateful to partake in. So stop into some sidewalk bistros without looking them up on Yelp first, order a local beer you’ve never heard of, eat something with a name you can’t pronounce, go spelunking in a cavern, the list is endless. Challenge yourself and your group to do something well beyond the boundaries of normalcy.

4.  Stay Hydrated.

A charley horse in your right leg when you’re going 80mph or faster is terrifying. And certainly having a wasp fly into your car on the highway should go without saying – so keep the windows up too, if you can.

5. Music is Life.

I know Ted and Marshall in “How I Met Your Mother” showed us how great a road trip can be when you blast “I’m Gonna be (500 Miles)” by the Proclaimers, but make sure you have a little more to go on than just that classic hit from 1988. A well-stocked iPod and an aux cable will do your wonders; likewise, a book on tape (provided you all have similar interests – see #1) can be a great way to help pass the highway miles.

6.  Always Remember – It’s an Adventure

You’re not going to like every part of a road trip. The highway miles can get boring, your friends may annoy you from time to time, and you’ll probably get a little sick to the stomach from trying so many new things. But don’t worry – it’ll be worth it when you’re toasting hurricanes and hand-grenades and eating oysters on Bourbon Street in New Orleans, or devouring a 72oz steak in Texas, or losing your life savings at the Bellagio in Las Vegas, or whatever it is you all set out to do in the first place. Life is certainly a grind, but it’s also an adventure, like Jack Kerouac said in On The Road, “But why think about that when all the golden lands ahead of you and all kinds of unforeseen events wait lurking to surprise you and make you glad you’re alive to see?”