How to Rally the Troops When It Comes to Planning a Group Trip

Sixty percent of the time, you can trust strangers to take group photos with your cellphone every time

Sixty percent of the time, you can trust strangers to take group photos with your cellphone every time

Planning a trip can be a headache. This is true when just two or three people are involved, but even more so when you start talking about groups of five, six, seven, and beyond. Once you get past the initial challenge of lining up your schedules just so, then comes an inevitable avalanche of logistical questions.

When should you purchase plane tickets? Could you survive a multiple-hour car ride without pulling each other's hair out? Where will you stay? How will you get around? How will you decide what to do when you get there? Will you need to split off into smaller groups at times to fit everything in? How will you keep track of who pays for what? Will you still be friends by the time the trip is over?

I've been on a few study abroad trips with upwards of fifteen people and planning a night out in Buenos Aires or Beijing can get a little tricky when you have that many competing opinions. For the most part, however, those little international excursions were planned by the professor(s). The only time that planning a trip has practically been entirely up to me was when four friends and I flew out to Los Angeles for spring break during our final year of college.

Planning for that trip made me realize how difficult it can be just to get five people on the same page as far as travel plans are concerned. I can be a sporadic person, no doubt about it, but when it comes to putting together a weeklong trip like that, I like to have the details nailed down well in advance. As for the friends that accompanied me to LA? Well, let's just say they didn't necessarily have that same sense of urgency. Thankfully, we were able to skip that initial step of getting our schedules to line up — we all had the same week off for spring break, wouldn't you know — and were able to jump right into the logistical fray.

"The lesson here is that planning in person, if possible, is the best case scenario."

First item up? Ordering our plane tickets. Now, I still fly on planes infrequently enough that purchasing airline tickets causes me just a pinch of anxiety. Like, you're typically throwing down a couple hundred dollars or so and a lot of tickets are non-refundable, so you need to make sure every little detail is right. On top of that, if everyone in your group is buying their ticket individually — as we did — it's probably best, if possible, to physically be in the same room with one another to make sure you're getting a seat on the correct flight and that everything matches up as it should.

Personally, I had qualms over clicking that button to make my ticket purchase final before knowing that my friends had done the same. But maybe I'm just weird like that? In any case, the lesson here is that planning in person, if possible, is the best case scenario.

The next question up: where will you stay? And if you know me at all, or have read previous posts on this blog, you already know where I'm going to tell you to turn on this one. That's right, hit up the ever-convenient person-to-person rental site known as Airbnb. Even though it would only be the second time I'd ever used the website, I didn't consider any other options when attempting to find a place for us to stay in LA. It just wasn't necessary. (And as always, if you're looking to get $40 off your first trip, here's where you should go:

As you can see here, Airbnb has expanded recently to offer not just accommodations but also "experiences"

As you can see here, Airbnb has expanded recently to offer not just accommodations but also "experiences"

For getting around, I knew we would want to rent a car to avoid racking up Uber fees. Depending on group size, which, again, was just five for us, renting a car could be a good option for you, too. If it does make sense, one easy-to-use site that I've had a good experience with in the past is Turo — essentially the Airbnb for cars.

Of course, if you have too many people to fit in one rental vehicle and you'd rather not get two, Uber and Lyft are always options you can take advantage of (given you are traveling to one of the many, many places that offer those services). They are generally always going to be cheaper than traditional cabs.

Switching gears a little bit, how about what you will do when you're there? Bigger groups of people do not always have the same idea of what constitutes a good time. Sally and Jessica may want to visit the art museum while Nancy and Jennifer would rather hit up a nifty outdoor market they looked up on the Internets, and you may not have time to do both with everything else you have planned.

In some cases, maybe you'll simply compromise and someone won't get to go where they want. But I'd say don't be afraid to split up and get in the sightseeing you want to get in. Plus, you'll be able to talk about Sally behind her back that way.

However you end up spending your time, it's important to be aware of your traveling companions' comfortability with spending money. If someone was wary of spending as much money as they did just to go on the trip in the first place, maybe it wouldn't be the best idea to force everyone to eat out at a five-star restaurant every night or to automatically assume everyone will be okay with the hefty price tag associated with visiting some attraction, such as a theme park.

Speaking of cash money, there is one more important tidbit we need to get to, and that is how you will keep track of funds during your trip. Sometimes it will make more sense for one person to cover the cost of something for the whole group and, when this happens repeatedly, it's important to keep track of who owes what to whom. A great little app for this is Splitwise, a totally free way for you and your friends to keep tabs on finances whilst out on the road.

With the app, you can split bills evenly among as many people as you need to. Not everyone was in on a certain expenditure? That's okay, because instead of always blanketing the entire group, the app allows for you to pick and choose members of your party to split a bill with, too. (Side note: Splitwise is a great app for figuring out rent and utilities with your roommates, as well.)

Whew, okay! I realize this probably wasn't the most informative post you've ever read in your life, but I do hope you got something out of it. And maybe, if you employ any of the advice I had to give here, you'll be able to answer the final question I asked all the way back at the beginning — will you still be friends by the time the trip is over? — with a resounding "yes!"