1. Choosing whose car to go in
Always go in your car. That way you are in control of who drives and that could end up saving your life if the other person is a bad driver.
This past weekend for the dive trip to Shevlin, MN I found myself praying to whoever would hear me that I wouldn't get killed because of the girl's crappy driving. She hit the rumble strips more times than I could count and we found ourselves on the wrong side of the road a few times.
If you know the person and you know their driving won't kill you, then your next items to consider are gas mileage and interior space.
2. To room together or not
First question to ask yourself is, do you know this person well enough you would feel comfortable to room with them. If the answer is yes, then you should be okay. But you also have to consider when they go to bed, will they talk your ear off until midnight as you try to sleep? Stuff to consider.
I ended up rooming with this girl and her mother came along. Biggest hotel mistake ever. She talked my ear off until midnight and when I pretended to be asleep they just yelled my name so I would "wake up." I was so tired I started grunting in response to what she was saying.
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Another thing you need to take into consideration is, do you need to get stuff done while on your road trip vacay? Stuff can be anything from homework to typing up a blog post.
I needed to do homework, so I went out into the nearby woods on a trail to do it because her and her mother were watching Madea. Let me tell you, there is NOTHING funny about a black man dressed as a fat, old, black woman.
When I came back from doing homework and consequently being eaten alive by the mosquitos I wanted to go to bed. They kept the TV on. TV + Attempting to sleep = Bitchy Niki in the morning.
3. If the other person's mother is coming don't even attempt to go together
Chance's are that person is co-dependent on their mother and their mother enables child like behavior from them. It may even be possible that the mother doesn't know how to take care of herself without her child. So watch for that when road tripping with someone.
If you even suspect that might be the case, save yourself the trouble with having to deal with ignorance and go by yourself. Sure it'll be more expensive because you won't be splitting gas or hotel costs but your sanity is worth those extra dollars.
Bonus: Always have a backup escape plan
I am fortunate enough to be able to fly just about anywhere, so I can always hop on a plane and head home if my sister "suddenly becomes deathly ill in the hospital." That's another thing, always have a very plausible story to go along with your fast exit.
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For the rest of you who are not that fortunate, you could always rent a one way car if it is that horrible. Car rental companies usually always have cars that need to go in one direction or the other. Call around and you'll find one. Most, not just Enterprise, will pick you up.