on the road: the art of planning a road trip


Fourteen. The number of states we drove through. Five. The number of days it took us to do it.

For as long as I can remember, I have idealized the road trip. Packing whatever you can fit into a bag and heading out onto the open road has always symbolized freedom to me. Those of you who spend most of your days behind a desk like I do, will understand. Monotony has its limits, and when the empty glow of florescent lighting grows dim, it’s time for a little adventure.

Road trips always seem to flourish organically. A word; a sentence; a story. Whatever it is, it ignites an appetite to seek out whatever it is we’re looking for. In our case, it was one sentence: “I’ve always wanted to see the south.” And we were off.

There were four of us, and soon our route was set. Five cities in five days: Nashville, New Orleans, Panama City, Florida, Savannah and Charleston. Ambitious? Maybe. Worth it? Absolutely.

We wanted our road trip to be spontaneous and unplanned. Classic. A nod to road trips of years past and the simpler times held with them. However, as much as we had romanticized the thought of driving off into the sunset, there were things we needed to consider. We had mortgages to pay, pet-sitters to find and jobs to get back to in time.We soon realized that we had to succumb to the times and forge some sort of plan.

Here are some things to consider if you too, would like to plan a modern-day road trip of our own one day:

Accommodations. To book or not to book? 

If you go the classic road trip route, you’ll probably be more inclined not to book your accommodations in advance. We set off not booking anything in advance and while that was fine because it gave us the freedom to arrive in any city whenever we wanted (and definitely kept within the confines of a “spontaneous” road trip), when we finally made it to Nashville that first night, we had to do a fair bit of searching before we found a hotel that fit into our budget. I will say that I enjoyed the “thrill of the hunt” though. With that said, if you decide not to book your accommodations in advance, remember that you will most likely  be staying in a tourist-heavy area, so prices are bound to be high. Also, make sure that there aren’t any holidays or festivals happening in the city at the time you arrive. I’ve heard horror stories of people not being able to find any accommodations, which would definitely be disheartening.

If you’re on a tight budget, I’d suggest booking most, if not all, of your hotel rooms ahead of time. Booking online is almost always the most cost-efficient way to go.

Plan Your Route Ahead of Time

Definitely plan your route ahead of time. One thing that can really damper a road trip is being stuck in traffic for hours on end, making a long drive even longer. First, consider the time of day you’re leaving. We live in Toronto, a congested city on a good day, where rush hour peaks at 8:00 a.m. Because we were leaving on a Tuesday, we decided to leave at 5:00 a.m. to beat rush hour. We also had to cross the U.S. border, and anyone who has tried to cross any border into the States from Canada knows that time is always of the essence.

Also consider construction zones. Because you will most likely be traveling on major highways or interstates for most of your trip, it’s a good idea to take a look at what areas are under construction and plan alternate routes if necessary. Google Maps is a great planning tool, because not only does it help map your route, it shows you the areas under constructions on the way to your destination.

Your Budget

I don’t think most people set out on a road trip with copious amounts of money, so budgeting is always a great idea.

If you’re traveling with a group of people, decide how the trip costs will be funded in advance. To cut out any awkward money moments, we each put the same amount of money into our trip fund and used it on gas, accommodations and food. As we neared the end of our trip and our funds, we each tried to split evenly the remainder of the trip expenses.

Balance coupled with compromise, our road trip was successful. By the end of our trip, we had traveled through fourteen southern states in five days, each of us getting our fair share of southern charm and sweet tea along the way.



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