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7 Steps for Planning a Road Trip

Travel Insider Guides
by Spencer Klein Sep 13, 2012
Neal Cassady style road-tripping isn’t for everyone. These guidelines can help you define a road experience of your own.

“I WOULD LIKE to take a roadtrip.” Great, where do you start? If it’s your first time, go by the seat of your pants just as you have to, and if you’re lucky enough to have any direction at all, let it be Neal Cassady babbling incomprehensibly over the headrest or off the page at night when you’re not behind the wheel, until the voice carries and everything everywhere is peaking skyward and sufficiently explosive and mad.

When it comes to that one roadtrip — absent of all inhibition and planning — shelves of travel memoirs all carry one thread (aside from misadventure): the fruits of serendipity and chance are undeniably sweet. But roadtrips are meant to mature, just as their drivers are — it’s down that road that you might plan to roll in the future. Here are a few guidelines to pave the way; take them on in order.

1. Fix a start point, destination, and route. A to B, and maybe back to A. It doesn’t take long for a roadtrip to lose it’s romance, or even become stressful when goals aren’t clear. Set down the intention, and don’t discount variables, like a return flight home, or a more economical route one way and an attraction-filled route the other way.

Your route can be subsequently modified by other guidelines, but more than anything, you are establishing a desire for a type of experience — one defined by the route you lay out.

2. Clearly define your resource bank. How much money do you have to set aside? And how much time? These two questions will frame every other detail, and they often go hand in hand, so come up with a resolute answer for both. If you’re planning to travel with a partner or two, this is often the make-or-break element for launching, or enjoying, the trip.

Remember to plan adequately for the period when you return home if you’re leaving a job, or ending a lease; the end of a trip won’t seem half as sweet otherwise.

3. Tactfully align the usual suspects. Think about the ingredients here. You have plenty of friends that are great in a group, or great for an hour, or great over a beer, but who’s good when shit hits the fan and you’re camping in the desert with a flat?

You want to be free in every sense of the word, not thumbing your smart phone because you’re unsure of the next exit, or your tank is empty.

And if Nancy and Johnny are griping, it’s your own fault you didn’t realize that he kissed her cousin’s girlfriend when they were going out six years ago. Financial alignment is also a huge factor for ensuring cohesiveness; don’t underplay the importance of means.

4. Mark the tipping point and fix the dates. Everyone has a friend who talks the talk, and then doesn’t show up for the game. Once you have the primary elements established, make the midpoint, which is also the tipping point, a definitive moment. This is crucial in a group, and alone. Make the decision by choosing and marking the dates on a calendar. Everything that follows will be much easier if you do.

5. Fill in the details. Creating a bank of waypoints is putting flesh on the trip, and when it’s done right, it will save a lot of time, gas, and energy. The concept of driving through the countryside is easily romanticized, while planning for the attractions and little stops along the way is often overlooked. It should be the opposite. You want to be free in every sense of the word, not thumbing your smart phone because you’re unsure of the next exit, or your tank is empty.

Knowing that you have a two mile loop to hike after about 60 miles definitely helps with the numb butt. Stockpile your ideas somewhere accessible, and visualize their possibility along the way. A bag of mixed nuts will probably serve if that sweet looking cafe you found is an extra 30 miles off track.

6. Reach out. Find the friends and family along the way, and get in touch with plenty of lead time. More often than not, they’ll end up reaching out to their own friends and family, and you’ll end up with more funds to live it up down the road. Homemade dinners and an uncle’s guest room are way underrated. Just remember to show up with a fresh loaf of bread, and a bottle of red.

7. Take two preventative measures. It absolutely sucks to (a) have car problems in the middle of nowhere, or (b) return home broke, in debt, with no plan at all. Do a bit of work on the front end to plan for both. Change the oil and filter, then stash some money in a savings account at the very least.

Worth checking out

Roadtrippers is a self described travel planning tool that helps you design, calculate costs, and make reservations for a roadtrip in the continental US. The site’s unique content relies on the “curation of local experts and travel writers.” For a newly launched site, the navigability and feel are surprisingly intuitive and smooth. Any preconceptions of boredom and spreadsheet-derived design quickly disappear on a platform that almost feels like a travel planning collage.

I plugged in the starting point, waypoints, and final destination of a trip I’m planning through the northwest this fall and instantly knew I’d be on the road for 1560 miles, spanning 26:14 hours, with fuel costs running $265 if I didn’t take the Leaf. Oh, but it took me through the desert. No worries there: I just toggled the route over to the I-5, so I could head through California.

With the route set, I added a variety of Places along the way that were easily filtered by their distance from the planned route, and cleverly divided into subsets that were undeniably “curated”. Among them was a health food store at the base of Mt. Shasta, an independent movie theater in Missoula, and a good river for tubing in the Bitterroots. I estimated costs for each, as well as several other stops along the way and had a great feeling for what I’d be spending.

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