The #1 Thing: Who You Bring on Your Road Trip Can Make or Break It!

"I have found that there ain’t no surer way to find out whether you like people or hate them than to travel with them."
Mark Twain

It’s something that everyone knows, but seems to completely forget when planning a trip – especially a road trip. Who you travel with is the number one thing you should figure out before you decide anything else.

Road Trip

Okay, so you might be saying – if I go with my best friend everything will be perfect!

Wellllllll…. that’s not always the case. Take the time I went on a spring break trip with one of my best friends in the world, my cousin, Yvette. She is a wonderful and brilliant person, but she was the worst possible choice for a wild Spring Break vacation.

First of all, she was getting over a tough breakup and wasn’t “fun” right then at all. A quiet vacation at a mountain retreat would’ve been more up her alley. Second, and more deadly, she had never gone in for the whole crazy party scene even when she wasn’t depressed. To put it plainly, she hated it.

We had other great trips together, but that one wasn’t a good one due to bad timing and her generally low opinion of wild parties.

Another road trip I took with a bunch of friends was a huge success – because they were the right bunch for it. It was up the East Coast and over to Block Island. Everyone was into having a great big “party on wheels” and no one wanted out. We sang songs loudly all the way, tried every restaurant and bar that looked interesting, stayed in a dumpster of a hotel that we all ended up joking about, and generally had a blast.

I list these two because they are so similar – “party” trips. I’ve taken all kinds: romantic, family, destination, and mellow trips with friends. In every case, it really matters who you choose to bring.

If you don’t have a choice (your family, for instance) or you insist on going with that person (best friend), make sure that the trip itself is a good fit for the people going. Kids are going to get antsy and irritable going on a museum-tour/fancy B&B type road trip and you’re better off avoiding one long party scene if you’re with your significant other. Take their personality and interests into account when planning your trip and destination. The destination and the people traveling together must be a good match if you want it to be a great time for everyone.

Also be sure to clear up any old resentments/arguments before you go – anything that’s been bubbling under the surface. I can guarantee you that whatever it is, it will come out while you’re on the road if you don’t get it out ahead of time and it can really ruin your trip.

Every bad argument I’ve had with one of my friends took place on a group trip – one trip was two weeks long driving all over Ireland (southern) and the other was a trip up the California coast from LA to Carmel. All that time with the four of us crammed together in one car, having to constantly make group decisions, everyone trying to get along; it all took its toll. She had issues with me, and when you put problems in the pressure cooker of a road trip, they explode! She sniped at me, I stormed off, we had it out – phew!

Try to sit down before you go and hash any problems out. If you really don’t want to talk about whatever it is, reconsider traveling with that person. A vacation is supposed to be fun, and it won’t be if you end up arguing the whole time.

You will find if you take enough trips that you have people you prefer to ride with and those you would rather leave behind. It doesn’t mean you’re not friends or that you don’t love each other – it means you’re not the best fit for a road trip. Road trips are real litmus tests of how compatible you are.

In fact, I think it’s a good idea to take your fiancé/fiancée on a road trip before getting married. While we were still dating, my husband and I went on a trip through the Florida Keys and learned so much about each other. One thing’s for sure, my husband isn’t happy unless he has a tropical drink in his hand and is lying in a hammock strung between two palm trees on a beach!

You owe it to yourself to take the time to figure this out. The choice of your road trip companions will make or break your trip – choose wisely!

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