Vacationing with Friends: 9 Tips for Taking the Trip

When I was young, I used to envision my life as an adult. Didn’t you? I observed my parents invite their adult friends over to hang out and I’d think about how I would host people at my own house for dinner or social events when I grew up. I would think about how I would decorate my own home as an adult. And most extravagantly, I would fantasize about all the really cool vacations I might take with my friends when I was fully-grown. I envisioned cruises and jetting off to beach resorts. And then I got married, had children, and the reality of parenthood hit. The idea of going on a vacation with anyone else felt stressful, and unreachable. Where would we stay? What would we do? And how would we ever align schedules with another family?

Image: kids on the beach vacationing with friends

There were so many questions to answer, and there was also the challenge of finding the right friends to vacation with. Because you can’t vacation with just anyone. Am I right . . .  or am I right? 

In February 2019, I took the most perfect girls’ trip with a dear friend to Oklahoma to do all things “Pioneer Woman.” That trip was successful and we had such a lovely time. It spurred conversation about how we should get our families together for a group vacation. We toyed with the idea in fall 2019 and early 2020. And then, well, 2020 was what 2020 was. So we didn’t move the plan forward. 

However, in late fall 2020 we began discussing the possibility of taking the trip we had dreamed about over a year earlier. We knew there were locations we could safely visit despite whatever might be going on in the world at the time of our vacation. On New Year’s Eve, while our two families rang in 2021, we got to work researching locations and discussing the possibilities. By February, we had booked cabins on the same resort property in Northern Michigan for early June. 

Our trip was fabulous and will be one of my most treasured memories. I would do the exact same trip with the exact same people over again in a heartbeat — and I’m not just saying that because our travel friends will likely read this!

Vacationing with Friends: 9 Tips for Taking the Trip

Don’t Assume All Travel Has to Occur During the summer

Although our trip took place in June, I took a girl’s weekend trip in October and my family also spent five days with friends and their kids at an Airbnb over Thanksgiving week. If your friends have a free weekend or vacation time to burn, you can travel anytime!

Thoughtfully Choose Who You Will Travel With

As I said before, you can’t travel with just anyone. As lovely as vacations can be, they are also stressful and sometimes you are at your best and sometimes you are at your worst. Choose friends who can handle both versions of you. Also, we found it beneficial to have kids similar in age. Our kids are 6 and 9 years old. The friends we traveled with have four boys ranging in age from 4-12 years old. It is possible to travel with friends who have differently aged kids, or no children at all. It’s just important to remember the limitations created by that. For example, if we had traveled with friends who had toddlers, there would have been mid-day naps and much earlier bedtimes for their little one(s). Additionally, our kids would have only had each other as a true playmate. For our trip, the kids all meshed very well together, everyone always had a playmate around their age if they wanted one, and all the kids had similar bedtimes.

Discuss Location, Type of Travel, and Non-Negotiables Up Front

We knew right away we would drive. This was easily agreed upon. But it’s worth a discussion with any friends you might travel with. As we discussed the “where” for our trip we toyed with a western state and discussed staying in rustic cabins at a campground. We realized the cabins we’d found were not air conditioned. And quickly learned that a non-negotiable for the men was air conditioning (or at least a location that would be cool enough at night that lack of air conditioning wouldn’t matter). We also agreed the max distance we wanted to travel by car with 6 children was 8.5 hours. This helped produce a radius of travel around our home and created a natural limit to the locations we could visit. Ironically, our chosen destination was exactly 8.5 hours from our homes.

Image: cabin view while vacationing with friends

Decide What Lodging You Prefer and Will Thrive In

We ended up booking two separate cabins on the same summer resort property. The cabins were across a driveway from one another and both had full kitchens. Having our own space to retreat to when we were tired or needed down time was key. Each family was able to have family time, but we were close enough to share space as much as we wanted. We each shared cooking responsibilities and took turns walking side dishes or desserts across the driveway for a meal at one house or another on any given night. We also ate some breakfasts together and other mornings we did the first meal of the day quietly as a family.

Know Your Strengths and Weaknesses for Planning

I can be a little “extra” so my friend knew I would happily research every possible activity and adventure, plan a thoughtful itinerary, and share options with the group. My friend cooks for four boys on a regular basis. Cooking for a family of six isn’t much different than cooking for ten so she took the lead on planning out meals for the week. We used a Google spreadsheet to organize our thoughts and each of us added information so the other could reference it as needed. 

Make a Travel Plan

A little bit before our trip we sat down to map out the route, and planned stops along the way. We knew bathroom breaks couldn’t necessarily be planned, but we wanted a set lunch stop and we wanted to be strategic. We figured out where we would be on our route around the lunch hour. Then we Googled parks in the area. We found a small park in a neighborhood. Once we identified the park we found a sandwich shop five minutes away. On our travel day we had a mid-day stop with a chosen restaurant and a place to eat that would also allow our kids to burn off some energy. It gave us a location to aim for and eliminated any frantic texting about where and what we wanted to eat lunch.

Take Advantage of Having Multiple Adults on the Trip

We realized that with two couples on the trip we had built-in babysitters. As a result each couple took a date night and we entrusted our kids with the other couple while we snuck away for a dinner out! It was so novel to have to ability to have a date night while on vacation!

Image: date night while vacationing with friends

Don’t Spend Every Minute Together

We planned many activities over the course of the week for our two families to do together. We visited water falls together, hiked, and visited museums. However, on some of our day trips we split up mid-day. One day we traveled to a beautiful beach and spent a gorgeous morning on the water. After lunch our friends wanted to head back to the cabins. Our family opted to stay and explore the town. A different day we visited an island. We spent the morning together and enjoyed lunch as a group. After lunch we split up while they visited some shops and our family biked around the Island. Later we bumped into them at the shops and learned they had also biked the island. Each of our families enjoyed the same activity but made memories as our own family unit. The best part was that each of us felt no negative feelings about splitting up and doing our own thing.

Image: family bike ride while vacationing with friends

Make a Shared Location to Put Photos After Your Trip

Both families took a lot of photos on our trip. We thought it would be a great idea to make a shared folder to put all of our photos so we could exchange them between the two families. It is still a great idea, but admittedly, I haven’t done it yet and our trip was in June! I Guess I should add that to my to-do list . . .

You could spend a lot of time thinking about reasons why a trip wouldn’t work with friends for one reason or another. But, seriously, make the plans. Take the trip! We have zero regrets. Enjoy vacationing with friends!

Linda is a Michigan native who moved to Iowa City in 2011 and hasn’t left yet. She and her husband of twelve years, Jacob, have two spunky kids – a kindergartner and a third grader. Linda works full time at the University of Iowa as the Administrative Director for the Medical Scientist Training Program. Together, Linda and her family enjoy cheering for the Nebraska Cornhuskers (shhhh!), going on adventures both big and small, and playing board games (they have over 100 and will play with anyone they can talk into it). Linda is often told she has two volumes: on and off, and she will enthusiastically respond to any news you tell her. No matter the volume she uses, Linda is an “old soul” with a love for baking, embroidery, and old movies.


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