View of sun setting over the blue ocean, with view of beach, a kite, and clouds in a blue sky

Traveling with Family: Top Tips For How to Make the Most of Your Trip

Do you love traveling with family, or do you dread it? Years ago, we didn’t lean into vacations with our families. Our paid time off was limited, and it just wasn’t a priority for us.

Our wake-up call came in late 2020, when my dad passed away unexpectedly. We realized just how limited and precious time is, especially with our families. We’ve shifted our mindset to welcome and even prioritize travel with our families.

We started slow, with a couple cruise vacations with our parents (side note: cruises can be a GREAT way to travel with family). Then his family (parents and adult brother) decided to rent a place in Florida every other Christmas starting in 2016 (besides 2020 due to COVID). One Christmas my parents even joined us and rented a place nearby. Having two sets of families there at the same time was a bit tricky, but memorable!

Since then, we’ve traveled for two weeks with his parents for a whirlwind tour of California (including Yosemite National Park), and I traveled with my mom to the Upper Peninsula in Michigan, where she was born. Until of course, I got COVID, and we had to promptly drive home after reaching Marquette, ugh!

This year we’re upping the ante with an Alaskan land tour and cruise with his family, I’m returning to the UP with my mom in July, and we’ll be in Florida over Christmas again with his family.

Needless to say we know a bit about traveling with family.

Based on our experiences, today I’m sharing our top tips to help you make the most of your travels with family. Because let’s be honest…

You don’t just want to survive the trip, but you actually want to enjoy the trip, together!

When Traveling with Family…

When it comes to these tips, let me be clear about a few things.

First, I do realize everyone’s family dynamics are different. My non-negotiables when I travel with his family vs. when I travel with my family are different. The key here is to think about and understand what’s important and non-negotiable to you before you embark on a family trip. Start out on the right foot.

Second, I do realize some of these tips may impact the overall trip cost. The good part is that you and your family get to prioritize what’s most important to you. You get to decide!

Lastly, these tips are applicable regardless of who in your family you’re traveling with, be it your household/immediate family, or adding parents, in-laws, siblings, etc. into the mix.

Okay, let’s jump in.

Top Tip #1: Everyone Gets Their Own Space

Ever heard the phrase, “absence makes the heart grow fonder?” Well, a similar statement can be said when traveling with family in that everyone needs to have their own dedicated space to be able to enjoy the time when everyone is together.

My number one priority when traveling with family is everyone having their own space.

When we travel with his family, it is non-negotiable that we have our own bedroom and bathroom. I don’t want to run the risk of running into his family when I’m trying to go to sleep, brush my teeth, take a shower, etc.

When both of our families traveled to Florida for Christmas, I decided early on my parents needed to have their own place (thankfully they agreed!). While it presented some challenges having them a few minutes down the road, the overall experience was more enjoyable for everyone.

Space can be incredibly important for other dynamics you may not think about. For example, maybe you have a family member who always fall asleep to the TV every night, whereas others need peace and quiet to sleep. Or, maybe you have night owls and early birds traveling together; both need space to stay up as late as they wanted, or get up as early as they wanted without infringing on others. Traveling with children can also impact space, including places to play, take naps, gaming, etc.

Space provides everyone the opportunity to take a break from being together as a group. I don’t know about you, but I’m not accustomed to 24/7 time with our families. Having your own dedicated space can provide the balance you need to rest and re-charge. Space may also help you avoid flying off the handle when your mom insists on watching Hallmark movies for the third day in a row due to bad weather, but you have no bedroom to retreat to because you’re sleeping on the fold-out sofa in the living area… Having the right space can truly make or break your trip!

Top Tip #2: Everyone Has the Opportunity to Give Input

Getting input from everyone is important when traveling with family. This starts before the trip begins, early in the travel planning process. Whoever coordinates the travel plans (that is, me!) has the responsibility to ensure everyone involved has the opportunity to give input and be part of the decisions as the trip comes together.

During the trip it’s important to check in with the group on activities, places to see, things to do, and what and where to eat. Let me be clear… You won’t always reach consensus. But, giving everyone the opportunity to give input will help you avoid the cranky person who makes it clear they were NOT okay with a specific activity by making it miserable for everyone else.

Now, this doesn’t mean everyone will feel inclined to give input. Some people may not feel strongly about some aspects of the trip (specific location, type of lodging, mode of transportation, etc.). But, maybe they feel very strongly about restaurants and activities they want to check out during the trip. It’s okay if they don’t give input, but they still need to be asked for thoughts.

And about reaching consensus… What if everyone doesn’t agree on what to do, eat, etc.? Great question, which leads me to my next top tip…

Orange sunset with kite in blue sky and clouds with beach and ocean
Sunset in Indian Rocks Beach, Florida

top Tip #3: Not Everyone Has to Do Everything Together

Now listen, I know this is probably going to upset some of you out there who believe that the family trip isn’t successful unless you spent Every, LAST. Waking. MINUTE together. But, can’t we all agree that we’re not always going to agree on what to do, eat, etc.?

Seeking 100% consensus on every little detail is setting yourself up for failure, because it’s impossible.

Let’s embrace that, and move on. I truly believe allowing everyone the flexibility to do their own thing from time to time will actually enhance everyone’s trip experience and time spent together.

If you think about it, splitting up to do different things could provide the unique opportunity for family members to spend one-on-one time together, for grandparents to spend precious time with their grandchildren, or for the moms who just wants to sit on the beach and read uninterrupted.

During our two-week 2022 California road trip with his parents, we intentionally built in a few days where we could go off on our own adventure. One day was during our time in Yosemite, when we did a strenuous hike. We built in a second day near the end of our trip in San Francisco when we wanted a down day and his parents were still eager to explore the city. There were also meals during our time in California where we each did their own thing.

When we came back together we were refreshed and able to connect by sharing stories of what we did.

Him and his parents at McWay Falls during our California road trip

Tip #4: Adjust Your Expectations

My last top tip for traveling with family is to adjust your expectations. In fact, if I’m being honest… Lower your expectations.

When families travel together, the mix-mash of each person’s preferences, daily habits, routines, preferred activities, etc. are all thrown in together. These dynamics will undoubtedly create friction at times. And that’s okay. We’re all human!

Adjust your expectations by acknowledging there will be frustrations and even some tension. Expect that you will get annoyed, for example, when the TV is always on, even as background noise, even when no one is watching it. Because, that’s what they always do. Expect you will have to make some concessions, like eating some meals in when you prefer to enjoy new food and restaurants when you travel, or watching TV together in the evenings when you prefer quiet time (although, if you have your own bedroom or space, maybe you can do both!).

Adjusting our expectations allows us to take the pressure off. Of course we want our family trips to be perfect, for everyone to have a great time, want to be together every minute, and love every minute of it. But, because we’re human that’s just not possible.

When we expect some bumps in the road along the way, the bumps won’t have as much of a negative impact on our experience.

Those are my top tips when traveling with family! I’m curious though, what tips would you add to make the most of family trips? Tell me in the comments below!

We’ve got a very busy May coming up! We’re attending Camp Mustache Midwest where I’m facilitating a conversation around Finance Independence and Personal Relationships, we’re traveling for my brother’s wedding, and many other fun things!

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