Tips for Traveling with Other Families

“The more the merrier” can get a bit harrier when traveling with friends. You might be used to doing things a certain way while they have the opposite viewpoint and when kids are involved—then all bets are off! But now that I have successfully taken multiple trips with friends (and the amount of kids who join us just keeps growing) I have learned a thing or two about how to make the most out of our getaways. So here are my tried and true tips for traveling with other families:

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I’m in the camp of people who think that the anticipation of a trip is almost as fun and exciting as actually being on vacation (except when you are escaping to the tropics during Chicago winter—then floating in the pool with a cocktail is DEFINITELY better than the anticipation) so coming up with a good travel plan is key, especially when traveling with other families.

Coming up with a destination that is family-friendly with ample things to do and within everyone’s budget is KEY (and one of the reasons why our group takes a yearly trek to Wisconsin Dells). Let everyone share suggestions and then vote on which destination is the best fit for EVERYONE. Stumped? Check out Living Social deals and go from there.

Another factor to consider is everyone’s work and school schedules. Some may be flexible—others may not. Try to be as respectful of everyone’s situation as possible and be creative. For example, you might all arrive or leave on different days but still have quality time together in between different arrival and departure dates.

Finally, picking out a resort, hotel, or home can be a bit tricky. Checking out reviews (use my travel section to check out my family’s top travel picks) is always helpful, as well as using social media to ask other family and friends for tried-and-true recommendations. Starting with VRBO, or Home Away is a great way to get the vacation-planning ball rolling.


My sister doesn’t like to sit still while when I’m on vacation, I try to move as little as possible. But when we travel together, we both give in with one day of activity and one day of relaxation—or we happily agree to do our own preferred thing. The same thing can and should hold true when traveling with other families. A great way to have some fun adventures and s t r e t c h your budget? Checking out all of the different CityPass options.

For some families, having separate bedrooms to ensure uninterrupted nap time is key, while for other families having a kitchen to cook meals is a non-negotiable. Whatever the case may be, talk about one another’s preferences so everyone is happy with the accommodations and activities.

Don’t be afraid to break off for a bit if it is best for you, your kids, or your sanity. Traveling can be stressful and an hour away from the hustle and bustle can help alleviate it.


When we take our yearly group trip to Wisconsin Dells, each family divides and conquers the list of packing supplies so that everyone shares responsibilities and no one feels burdened. For example, one family hosts an early evening “happy hour” with drinks and snacks while another family prepares breakfast the next morning. Everyone shares the responsibility so that the trip isn’t all work or all fun—instead, a perfect mix of both.

While you might have different parenting styles than the other families you are traveling with (I mean—NO parent or child is the same!), it is always wise to take the “all hands on deck” approach to childcare while traveling with other families. Our boys are past the diaper and nap time stage, so my husband and I were happy to give babies bottles and hang out in the baby pool if that meant that our friends could relax a bit. And when the husbands allowed us wives to escape to the swim-up bar for an hour—we fell in love with them all over again.

Don’t want to have to stress about getting great photos from your trip? Then check out Flytographer, my favorite travel hack. You can even get $50 off your shoot here.


Lastly, don’t forget that NO TRIP IS PERFECT, no matter what social media photos might suggest. Kids will have meltdowns, stuffed animals will get lost, drinks will be spilled—and everything will be okay. Promise. And while my tips for traveling with other families cover a LOT of things, they don’t cover everything. Be flexible and remember why you wanted to head out of town with your friends in the first place!

Don’t miss my travel tips and favorite travel destinations for Chicagoland families.

What are YOUR tips for traveling with other families???

Have fun!


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  1. Cassie says

    These are wonderful ideas for traveling with friends or family. I agree all parenting is different. Being a support system for your friends helped them to have a much nicer trip. That was awesome of you. Plus, they’ll totally want to travel with y’all again in the future. That’s a win-win. 🙂

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