How to Plan a Group Trip Without Losing Your Mind

Traveling can be an incredible experience. Exposure to new places, people, food and culture certainly has the ability to change your perspective on your life and the world.

Having said that, travel can also be a stressful and anxiety-driven experience if not planned well. Sure, getting on the wrong bus might lead to a new adventure but getting on the wrong bus to be stranded in a foreign place, with no cell service or somewhat trustworthy food nearby is a complete nightmare.

Of course, planning a trip for yourself and your friend or significant other might not be too difficult. Generally speaking, developing a game plan to avoid any nightmares is pretty straightforward for a party of two.

But what happens when you’re dealing with a larger group size and the logistical elements now seem like a jigsaw puzzle? Well, when I said before that traveling can be stressful, traveling with a group can be hell if not properly planned.

Here are some useful tips to put the right things in place so when you do travel with a group, you can avoid any serious issues:

Designate a co-planner

Wrangling a group and managing all of the communication and logistics for everyone can be daunting. Tap someone who is equally enthused about making a trip happen to help you research, plan and communicate to the rest of your group.

You also don’t want to come off as the trip dictator, so having a co-pilot will help you avoid that.

Do some research

Prior to formulating a guest list or booking places, see what’s out there to get a sense of pricing, availability and activities. For example, if the goal of your trip is to hang out by the ocean and enjoy happy hour at the nearest beach bar, where you ultimately pick will be very different than if you’re trying to have a ski weekend up in the mountains.

Also, your research will give you a general price range so you know what’s within reason for your trip. If you want a beach weekend, you’ll see that pricing will be drastically different in the Hamptons versus somewhere on the Jersey Shore. You can also get a sense of what accommodation options you have and which are available.

Get your group involved

Before you start booking planes, hotels and excursions, get a sense of who and how many people will be getting in on the fun.

If you’ve ever tried to arrange anything with a group larger than three, you would know this is easier said than done. We all have those commitment phobe friends or coworkers who give you the “oh yeah, maybe, I’ll check in on that,” line for a month straight.

To avoid the constant back and forth, first have the one on one conversations with people to gauge their interest. It can be a simple direct text (people tend to not respond to blast emails or large group chats). Make sure you include: the possible dates, locations you’re considering, general price range per person and other people that may come.

Once you get enough people who said they’d be interested, send out a group email recapping possibilities and give them a deadline to commit. If someone ends up getting FOMO and wants to come last minute, you can offer them a couch or air mattress if it makes sense.

Next up: Accommodations

After everyone has committed and you know how many people are joining, start looking into accommodations!

Look into every possible option. Hotels, airbnbs, cabins… everything. Until you see what’s out there, it will be difficult to know when you’re getting a good deal or when things are super overpriced.

If you’re considering an Airbnb (which is usually a lot cheaper when split 10 ways), make sure you have comfortable sleeping arrangements for everyone in your group. If you have a friend who is willing to pay less to crash on a couch, keep that in mind as well.

Side note: If you’re going somewhere that requires a flight, look out for cheap deals and have your group ready to book as soon as you find a good rate. Consider flying out on “odd days” so Thursday — Monday versus Friday — Sunday. Sites like Skycanner.com or Kayak give you a full month’s view on when flights are typically cheaper.

Set expectations & assign roles

After you’ve found a sweeeeet place, make sure to email your group right away. Let them know how much it will cost and where they will be sleeping. Setting expectations with your group is crucial. Having everyone know what they’re walking into will avoid any drama once you get there (insert Ramona Singer in Real Housewives of New York).

Also, make sure to give them a detailed list of what they need to bring or not bring (such as linens and towels). If you end up booking an Airbnb, give everyone a “job” i.e. something they can bring for the house. Paper towels, snacks, toilet paper, etc.

Put together a flexible itinerary

Traveling with a large group can be complicated. A lot of opinion, or a lot of lack of opinions. To avoid “well what do you want to do?” all weekend, put together a general game plan for each day. Let your group know everything is flexible and optional, but it will help keep everyone organized.

HAVE FUN!

You’ve set your group up for a successful trip, so relinquish control, sit back and have fun! Set the expectations the moment you arrive that this is your vacation and you’re not responsible for solving anyone’s individual problems once the trip starts.

I am the co-founder of @Whisck, a service that curates memorable out-of-office experience for and with companies. Get in touch! kelley@whisck.com