#Upandcoming #Quarterlifer

Reclaiming the quarter-life crisis, one hashtag at a time

#Quarterlifer How-Tos: How to Plan a (huge) group trip! (And not want to kill everyone involved)

Why hello there, friends! I feel like I sound like a broken record every time I post here, but I bear the same message: it’s been a while. Gosh, what have I been up to since last we talked? I moved, the bee eff moved in, had to soothe the poor traumatized no-longer-man-of-the-house kitty, weekend-long workshops to plan, leadership seminars to attend… Whew! And oh! The topic at hand: …HAD THE MOST EPIC GROUP TRIP EVAR!!

A little back story if you don’t know: I’ve got this pretty excellent group of friends.  Because we’re spread out across the country (ok, and Canada) it’s pretty rare (though maybe not as rare as it should be given the state of some of our finances) that we can get huge groups of us together. And, even when we do, it’s usually crashing on floors, sleeping 3 to a bed, only to be traipsing off to our respective homes a short few days later. So, for the last couple years, we’ve made a point to take time off around Memorial Day to get together and split a beach house with gorgeous views, random games, drinks a plenty and y’know, actual beds for most people. This year, I decided to take the role on planning the shebang.

Now, mind you, despite the fact that I love my friends and that most are PRETTY easy to reach online and via all forms of social media– planning a 5-day, 4-night trip to a location that none of us are from or have been to is no small order. And, as anyone who’s lived with friends can attest to, trying to balance the wants and needs of many different friends can be hard. I definitely learned a TON through the experience and just wanted to share some of the tips for planning a huge group trip — and not want to kill everyone involved.


Make a Timeline

Hopefully you and your group of friends already have a time when you’re looking to go on your amazing trip of epicness. If you don’t, I’d first highly suggest you figure out some dates that will work for your group. I like Doodle for planning purposes and have also heard good things about When is Good. Knowing a date when you’re aiming take your trip will help to plan backwards and make sure every little thing gets done. (Plus, employers love to get those time-off requests way in advance).

To build your timeline, start by going to your local office store (or <3 TARGET <3) and get a cheapy monthly calendar and plan out some major milestones like: pick a location, select accommodations, book flights/transport, etc. If you’re more the technological sort, great a new Google calendar and share it with your friends so that everyone can see. Don’t forget to give your friends a date that they need to commit by!

Pick your Team and Share the Load!



My team <3

My personal philosophy is that everyone cares about something. The great thing about having a big group of friends is that more likely that not, there someone (or more than one person), who cares about something. And, I figure, if people are going to be throwing fair amounts of money at something, they should be able to feel excited about the pieces that they care about. Once your group is able to settle on a general location, think about all the components of a successful trip. If you get stuck,  guess what? You’ve got a giant built-in advisory board to help you figure out what to do!

For our trip, I settled on the following categories for planning.






Then, I asked people to just pitch in and help plan the parts that spoke to them most. Drawing upon the passions and skills of the group not only keeps you from tearing your hair out but also helps you think of suggestions and ideas you may not have even thought of before. And, the more people that are involved in the whole planning process just makes everything more transparent which brings me to my next tip…

Communicate! …And then communicate more

Probably the hardest thing about planning a group trip (especially if your friends are scattered throughout the world) is making sure everyone knows what’s going on, when decisions get made, and why. The best thing that you can do is set up a method of regular communication with your selected group. I set up a Facebook group, but you could just as easily set up a Google group, an email list or even a whole website/blog, if you’re so inclined!

Anytime there’s a major decision, be sure to communicate it with your group. There’s nothing worse than feeling like you’re left out of something. Also, if you need things from your group — flights booked, payments submitted use whatever method you decide to send periodic reminders about it.

Plus, y’know it’s always fun to share relevant articles, pictures, tweets, and inside jokes. Just because it’s a personal vacation doesn’t mean that you can’t promote and create buzz around it like an event you might have at work!

Example of what you could use to keep the buzz up for your trip! Work it, Dumbledore! 

Keep Your Records! 

This may be just my new-found evaluation side talking, but keep a record of what’s decided and all of the reservations that are made. This could be an electronic file on your phone or tablet or a binder or both. Keep track of things like:

– Flight arrival/departure times, locations, and airlines

– Reservations (phone numbers, confirmation numbers, dates, contracts)

– Shopping lists

– Itineraries and schedules

– Payments 

It can also be a good idea to keep track, either in a spreadsheet or somewhere else, all the decisions you made. It can be super helpful if you’re planning on recreating a similar trip in the future.

Finally… get a sweet toolbox!

In this golden age of technology there are so many nifty tools and gadgets that can help you keep organized. Here are a few of my favorites:

Google Forms – If you aren’t using Google forms you should. I use this all the time both in my personal and professional life. It’s an awesome way to collect any type of information from flight times to phone numbers.

Google Wallet –  This is so so so much better than any online payment platform ever, you guys. Literally, all it takes is a Google account and a checking account. Then, sending payments is as easy as sending an email. You can also set up payments on your phone!

Kayak – One of the most frustrating things about going on vacation is finding a flight that doesn’t break the bank. Kayak is awesome because you can set up a location and tentative arrival and departure dates and then have Kayak notify you about the prices every week, or even every day!

Split it Quick – This little number is a Godsend for any non-numbers people. It is a super straight forward way to split payments (equally or by percent) and minimize payments across the whole group.

Have you ever planned a big group trip? What are your favorite tips and tricks?