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How to travel with a group (and not go crazy)

Travel is the perfect way to build memories that will last a lifetime. But even the closest families or friend groups might find traveling together a bit of a battle. There’s nothing like a trip to magnify our personality traits—both the good and the irritating. That said, experiencing a new place or simply getting away with the ones you love most is worth the bumps in the road.

Here’s a few ways to tackle group travel’s biggest obstacles before they even happen.

Photo by Djurdjica Boskovic on Unsplash

Picking a date

Can a trip be annoying before it even starts? Of course—just ask anyone who’s been on a group email simply trying to select a date! No one wants to sort through 30 emails with dates that work (intermixed with inside jokes sent reply all, of course). That’s why I love using Doodle. This free online tool allows you to create a poll with multiple dates. Simply email the poll to the group and everyone selects which dates work for them. Super easy!

Setting realistic expectations

The older I get, the more I realize that expecting too much often leads to disappointment. This is especially true when traveling with a group. It’s quite hard to get my family of four all ready and out the door at the same time. Now add grandparents, aunts, uncles and more kids to that mix and you’ve got a logistical nightmare.

Instead of being disappointed that things aren’t coming together in the exact way you imagined, go into the trip with a “what will be will be” attitude. The point is to spend time together, and if you’re stressed about a schedule or fulfilling some dream of the perfect vacation, it’ll bum you out.

How to travel with a group and not go crazy

Booking a House

Hotels are great, but for group, you really can’t beat a house. AirBnB and HomeAway are just a few options for finding a great rental property that everyone will enjoy. It makes eating together easy—not always the case when trying to dine out with a group.  Those who need to go to bed early (i.e. kids) can do so, while night owls can stay up late in the common areas. And hanging out tends to happen more organically if you’re all housed in the same spot. None of this texting back and forth about when everyone will meet up in the hotel lobby.

How to travel with a group and not go crazy

Figuring out Transportation

The process of renting a car has never been easier. If you rent cars regularly, you’re likely accustomed to walking down a row of available cars and just selecting one. However, if you’re traveling with a group, don’t expect the rental car company to have a SUV or minivan just hanging around. To ensure you nab a vehicle that accommodates your group, you definitely need to make a reservation. Trust me, it’s way more fun than trying to squeeze 5 adults and all their crap into a Chevy Malibu.


Talking about Budgets

Expectations play a huge part into the morale of a group vacation. This is especially true when it comes to budget. Some people might be willing to drop major moolah on meals or adventures; others might prefer to pack lunches and seek out free activities. Traveling with both types of people on the same trip is a recipe for resentment. Better to talk about the money stuff before you go. Yes, it can be uncomfortable, but it’s something we all should strive to be more open about. Ultimately, it will make your trip more enjoyable. And of course, if someone wants to do something special (or opt out), let ‘em! It’s their vacation, too, and no one said everyone has to do everything together.


Ensuring everyone chips in

We all have that one friend who suddenly has alligator arms when the check arrives. Fix that issue with the Splitwise app. This nifty piece of technology can track your group’s spending. So instead of the headache of splitting the bill at every meal, every grocery store trip, etc., you can all take turns paying as you go. Simply track what you’ve spent in Splitwise and by the trip’s end, it automatically sorts out who owes what. Magic!

How to travel with a group and not go crazy

Settling up

Yep, I’m still on the topic of money! There are so many apps that make settling up a breeze. Venmo is a popular one, allowing people to pay each other with a few simple clicks. It’s so easy that your younger brother is going to have to retire his regular “oh I forgot my checkbook” excuse.


Spending time together, and apart

Just because you’re traveling as a group doesn’t mean you should spend every waking moment together. If someone needs to unwind with a book or a nap, let them, and don’t make a fuss about it.

How to travel with a group and not go crazy

Letting everyone have a say

When you’re traveling with a friends or family, picking a restaurant, activity or even a radio station can sometimes feel like a battle. An old fashioned vote lets everyone voice their opinion. Conversely, you can take turns choosing.


Divvying up tasks

There always seems to be one person in every group who gets stuck doing all the dishes, cooking all the meals, or planning everything. Unless you’re traveling with your butler (wouldn’t that be nice?), these responsibilities should be divided amongst the group. Chipping in gives everyone a little skin in the game, and lessens the chance of resentment. Assign everyone a meal to take charge of, or a day it’s their turn to plan an activity.

If you’re typically the person who deals with the majority of the tasking, I challenge you to relinquish some control. Let your fellow travelers get more invested in the experience. At best, you’ll enjoy just being a long for the ride without the pressure of taking care of everything. At worst, your compadres will appreciate all that hard work you do!

What are some of your best tips for traveling with a group? Share in the comments!

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Travel is the perfect way to build memories that will last a lifetime. But even the closest families or friend groups might find traveling together a bit of a battle. Here’s a few ways to tackle group travel’s biggest obstacles before they even happen.

This Post Has 6 Comments

  1. Samantha,

    We tried the other way ( travel with a group AND go crazy). This looks much better. Thank you so much for the tips.

  2. Went to Italy and with my daughter-in-law and my 8 year old granddaughter. It was Great! She made all our travel arrangements saved us quite a bit of money. I compensated by buying most of our meals. We each bought our own take home gifts and had cut fun buying each other cologne and fans. We also had great fun taking pictures of each other. I took a solo trip to Assasi and my daughter and granddaughter enjoyed a day together. What a glorious time we had!

  3. We have traveled as a family of 6 for several years and use a lot of your recommendations. The rental house is our favorite especially when we are spending a week in one place. For dinner choices, we draw straws to see which night you get to decide where we are going to eat (avoids hours of discussion and inspires you to talk to people and check out restaurants as you wander). Doing your own thing during the day or with different members depending on destination and interest. I would add another and that is having dinner together to review what each has discovered during their travels that day and then showing each other the day’s pictures that they have taken – with memory cards in most cameras you can use the computer screen or in some cases plug a camera into the TV.

  4. Great tips, Samantha.

    Whenever we’re with a group or friends – also meeting folks during our trips – there always seems to be a little hassel when settling up on a bill – especially in restaurants.

    When we are with a group, friends, etc. – upfront we mention to the waiter/waitress that we need a seperate check so we can pay via credit card and accumulate frequent flyer miles.

    I forwarded your tips to a few friends who are looking up to a trip to Egypt and a relative going on a cruise from Rome.

  5. Besides planning, make sure you plan some time for yourself. Been on trips with family and friends, and sometimes it can get irritating, so plan some time for yourself like going to a beach and relaxing by the water, or go to a plea the is a quick walk from your room like a shopping center or something and just walk and enjoy the sites. But do plan the for yourself, best way to keep from going insane.

  6. Great tips. I would “magnify” the recommendation that you allow — or even encourage — some alone time or time for couples to branch off and do things on their own. When I have traveled with groups, allowing people to do what they want during the day and meeting for drinks/dinner worked much better than too much ”forced togetherness”. Also, in addition to planning for expenses, I find it good to plan the high level itinerary. Some will want nothing but beach time and some will lots of activities. Best to get the discussion going early.

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How to travel with a group and not go crazy
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