Is the destination even the point of your trip, or is the road trip itself the “destination”?

Road trips, to some, are the embodiment of freedom. You and a friend or family member or two, with a few things packed and a destination in mind that’s far enough away to feel the miles gliding by. #VanLife’s explosion over the last half-decade has pushed even the more settled among us to consider taking to the road for a long weekend, a week, or even a month or longer. I’ve spent the last eleven months and over 30,000 road miles on an extended road trip, teaching outdoor education while living out of a vehicle, and while it may seem like the simplest form of travel – just hop in and go – plenty of forethought goes into a successful road trip. One thing you need to really evaluate is whether your car is honestly up for the trip. If it isn’t, then maybe consider a car online for purchase. You will also want to consider these questions and tips before you go driving off into the sunset.

The first consideration should be the people you want to spend your road trip with. Are there three close friends you’d like to come along, or is this a solo excursion? If you decide to travel with others, make sure you talk both travel and communication styles before the trip starts. Is one of you a planner, and the other a go-with-the-flow type? Does one person in the group get aggressive when things go awry, and another go silent? Traveling with even a single person that’s ill-suited to your travel or communication style is the fastest way to invite conflict into what should be a relaxed, if not relaxing trip, so choose your traveling companions wisely. Even if everyone’s the best of friends, make sure there’s extra space in whatever vehicle you’re taking, particularly on longer trips – the longer you’re out for, the messier things get, and the more stressful keeping close quarters can be. Knowing what to expect from each other and the rest of the trip can go a long way to reducing conflict along the way. Make sure you have reliable insurance from One Sure Insurance before you set off as this will prevent conflicts should an accident happen!

Once you’ve settled who’s coming along, you can move a little deeper into planning – and expectations. Where are you headed? Up to the Adirondacks, down to the Gulf Coast, west to the Sonoran Desert? Or maybe your objective is more urban – the clubs of Atlanta, the museums of Chicago, the beer scene of Denver? Is the destination even the point of your trip, or is the road trip itself the “destination”? If you’re not really sure what you’d like to see, browse websites like for national parks, landmarks, and monuments, or try Atlas Obscura for a quirkier mix of urban and small-town destinations. Use your destination to help you figure out a budget or vice-versa, making sure to leave some wiggle room for fluctuating gas prices. Clarity on the budget beforehand will ensure you’re not leaving anyone out of the fun while you’re on the road.

The vehicle is the lifeblood of any road trip, and it’s the one thing you shouldn’t have to worry about once you’re making miles. Whatever vehicle you take, it needs to be reliable enough to get you to your destination and back safely – so consider renting one for the trip if necessary or even making a trip down to Chevy Dealerships to try and find the right vehicle for your road trip. There’s nothing worse than leaving something this important to the last minute. The choice of vehicle is what will turn this trip into the best experience ever or one you would rather forget. So pick wisely. If you’re traveling with others, who is expected to drive? What temperature will the climate control sit at? Will you be bumping music or NPR? Will you pull over for every awesome thing you see, or will you be driving straight through? Negotiate before you get on the road to make sure your drive time isn’t bickering time.

When you’ve driven all you can drive in a day, how will you spend your nights? Are you planning to sleep in the vehicle? Bringing a tent? Unpacking in a Howard Johnson or a Ritz Carlton? Whether you’re traveling alone or with friends, having even a rough plan about where you’re sleeping before you leave will go leaps and bounds towards reducing stress on the trip. Decide among your traveling companions as to what your mornings will look like – will you be packing up the tent at dawn, or calling the front desk for a late checkout? A well-rested road trip makes miles, so sleep enough to stay safe.

Upon arrival to your ultimate destination, what does making the most of that spot mean to you? Are you going to do a bunch of hiking, climbing, paddling, or are you more interested in relaxing in camp, reading a book? In an urban destination, will you be partying all night and sleeping all day? Taking advantage of the arts and history in a location? Focusing on the food scene? Budget adequate alone time for everyone during a group trip, so that everyone has the space to do the things they’re interested in and new stories to tell the group when they return. Finally, when it’s time to head home, leave room for the quiet that comes of everyone processing the adventure on their own terms so that everyone can say for certain afterward what the trip meant to them.

After eleven months on the road, visiting everywhere from never-sleeping New York City to that breath-thieving Grand Canyon, I’ve learned that stories, pictures, and the human connections you foster along the way are the marks of a good road trip. Asking and answering as many of these questions as possible before you pack your bags will help to ensure that once you return home, those connections feel stronger, those pictures are full of memories, and those stories are anything but “what ifs.”


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