Planning a Multi-Person Trip

Over the years, we have taken many multi-person trips, whether it is just us and the kids, travel with friends, or even family reunions that have multiple families coming together to a fun destination. We've had them go smoothly and we've had a few that were... well... not so smooth. I've learned a lot about planning these getaways—here are three of my top tips:

1. Be more organized and detailed than you think is necessary.
2. Build in down time, free time, and alone time—set the togetherness bar LOW.
3. Take notes on what worked and what didn't as soon as the trip ends.

Be more organized and detailed than you think is necessary.

Every time I skimp on the prep side of things, I wind up kicking myself once the trip gets underway. Even though I have traveled dozens of times in the past few years, I have wound up forgetting things like pants (yep—I packed literally nothing but the ones on my body the day we left town), forgetting to make rental car reservations, forgetting to print boarding passes ahead of time, forgetting we can't bring knives across the border to Canada (I totally forgot that we had some camping gear still in the car from our last trip), and so many other forgotten or un-thought about things that it would take days just to write them all down.

I keep a running list of things we need to pack on my computer that I can copy/paste/print out as a starting template for future trips. This keeps me from having to start from scratch every time we go somewhere.

When traveling with multiple people, it is super important to know who is bringing what, so that nothing gets left behind or doubled up on. Some great examples of this are:

• Is everyone in charge of their own passes/passports/tickets, or is one person keeping tabs on everything for the group?
• If we're camping, I keep a separate food list for everyone so I know who is responsible for what so we don't end up with, say, five bags of chips and zero burgers or hot dogs.
• When we went to DisneyWorld with three separate families, we opted to all get our own rental cars rather than be tethered together. This let each family be flexible as the day wore on.
• Lake day with friends? Is everyone bringing sunscreen and their own floats, or are people sharing? And what is the carpool and towel situation? You'd be surprised how many times we have gotten somewhere thinking that floats were going to be provided and they weren't, or that we have brought bags full of towels and sunscreen just to find that the place we were headed had those readily available.

I also try to use a shared app everyone can comment on... sometimes this is as simple as a text thread and other times (especially if it is a faraway destination or a really long and involved trip) I will use Trello or Basecamp. The main goal, though, is that it organizes all communication and eliminates a lot of missed information. It also lets super organized people feel in control of plans, while keeping people that don't care much about planning still stay in the loop when needed.

Build in down time, free time, and alone time—set the togetherness bar LOW!

Taking a trip with people is awesome... until it isn't. Some people thrive in social situations and others just don't. This is not something to stress about—just take into consideration your own personal needs and the personalities and needs of your travel companions and plan accordingly.

You can have separate adventures and spend time apart and still have a killer time as a group.

I recommend taking a 50/50 approach:

• Plan to do 50% of your meals TOGETHER, and leave the other 50% open and flexible. This could be split up in many ways—perhaps you choose to always do breakfast and lunch alone, but want to snack and have dinners together for the whole trip. This is great! Or maybe you want to alternate days, where one day you are together for all of your food prep and eating, and then the next day you are all free to choose your own food options. You can always decide to pool resources ant eat together MORE, but this way you have freedom built in to eat out less, or maybe more than your companions, etc.
• Plan to adventure together for half of the time, and plan to go your separate ways the other half of the time. Again—you can always choose to link up and check things out together MORE, but having built-in down time gives everyone the freedom to explore without feeling like they are stepping on one another's toes.
• Plan to split AT LEAST 50% of the costs... and this is a big one. I find that there is alway cost overlap, and it is best to discuss this up front. Is it cheaper to buy airline tickets in a bundle? What about event tickets or groceries or lodging? Be prepared to split costs on a lot of the trip, as this will likely save everyone big bucks in the long run.

Take notes on what worked and what didn't as soon as the trip ends.

Derrick and I started doing this recently and it has made a huge positive impact in how we feel about the trips we take, and in how we plan future travels.

Sometimes we would end a trip and feel... underwhelmed or even frustrated. It took a while to put this into words to each other, but once we did we started to notice a pattern—we would come home after a fun adventure and then:

1. Feel bummed out that it was over
2. Perhaps feel a little lackluster about how a certain part of the trip went, or feel disappointed that something hadn't gone according to plan
3. Feel anxious about stepping back into "real life"

The list goes on and on. Finally—and I don't know what gave us the ideas—but we started taking notes on our trip when we were on the plane home, or in the car driving back. This has been a game-changer.

Now, we discuss what we felt went well, and what bombed. We discuss what we wished we would have done differently—good or bad. If we plan to go back to the same place again, we make a list of what we want to do next time. We talk about how we could set ourselves and the kids up for success in the next trip. We also talk about how we feel we scheduled things, because there's always so much to learn from every trip we take!

So whether your next trip is two people or 25, approach it with a detailed plan, build in pockets of peace and alone time, and take time afterward to evaluate the good, bad, and ugly, and you'll find you have an amazing adventure filled with more memories and less stress.

Cheers!