Road Trip Tips & Planning 101


This time, I'm calling the shots.

After the fabulously successful—albeit stressful—Valentine’s Day trip to New York, I’m excited for a weekend road trip somewhere a little closer to home: Chicago! Since my boyfriend was the brains behind the V-Day vacay, it’s my turn to do the planning.


Booking the Hotel

We know the hotel will be the most expensive part of our trip. I’ve already looked on some travel sites, and I’ve noticed that staying in a hotel further from downtown on weekday nights far from any holiday is the cheapest way to travel. I’m booking a hotel as far in advance as possible! But even if it costs a little more, I’m not going without a Jacuzzi tub, 24-hour room service and a quality breakfast (not the cheap kind with only cereal and dried out toast—yuck!).


Prepping the Car

We have a pretty reliable ride, but I’m not skipping the trip to the mechanic. He’ll change the oil, check all the fluid levels and rotate the tires to set us up for success. Then, I’ll make sure I have my driver license in my purse and the vehicle registration and insurance cards in the glove compartment before we leave.


Enjoying the Ride

We plan to set out early—before the sun is even up—to help us beat rush hour traffic in the city. We’ve timed it out, and if all goes according to plan, we’ll arrive in Chicago in the early afternoon and avoid dealing with rush hour there, too.

We’ll need plenty of tunes to keep us entertained, so I’ll bring my iPod, car charger and a few CDs just in case. To help us save a buck, we’ll pack a cooler with all our favorite snacks and drinks. We’ll have plenty of time to eat out once we get to Chicago. We’ll make sure to bring garbage bags to keep the car from becoming a trash heap.


I’m insisting that we stop for gas when we reach one-quarter of the tank. There’s no point in risking it. And I don’t care how much he argues; we’re both getting out and using the bathroom every time we stop for gas. That’ll prevent needlessly stopping again 15 minutes after we’re back on the road. Of course, if I have to go, he better pull over, no questions asked. I’m pretty sure that’s in our relationship agreement somewhere.


Driving Safely

I’ve already sat down with my boyfriend who, bless his heart, is not the best driver in the world. I have explained that there’s no way I’m letting our road trip get ruined by a stupid traffic violation. We’ll follow laws to a T by wearing our seatbelts, going the speed limit and using our signal when we change lanes or turn. We’ve got this!


We plan to bring sunglasses so we don’t go blind taking turns behind the wheel. I just know my boy will be watching me like a hawk when it’s my turn to make sure I’m driving to the high standard I expect of him.


Well, that’s what I have planned so far! Now I just have to figure out what to wear in Chicago this time of year…