Vacations are supposed to be relaxing. Sunshine, good food, maybe a beach read or two. But when you add your boomer in-laws to the mix? Suddenly, the trip feels less like a getaway and more like a reality show—part comedy, part chaos.
Traveling with your spouse is one thing.
Traveling with your spouse’s parents is… something else entirely.
Boomer in-laws bring their own set of habits, preferences, and quirks to every trip.
Sometimes it’s endearing.
Sometimes it’s maddening.
Most of the time, it’s a little of both.
While every family is unique, there are certain patterns that seem almost universal.
Here are ten things that almost always happen when you vacation with your boomer in-laws.
1. The daily early wake-up call
Boomers don’t sleep in on vacation.
While you might imagine leisurely mornings and slow starts, they’re often wide awake by 6 a.m., ready to go.
They’ll knock on your door or send a text at 7 a.m. sharp: “Are you up yet? We thought we’d grab breakfast before it gets crowded.”
Even if you stayed up late the night before, they operate on an internal schedule that doesn’t shift just because you’re on holiday.
By the time you’ve had your first cup of coffee, they’ve already been out for a morning walk, scoped out the hotel pool, and chatted with half the staff.
Sleeping in simply isn’t part of their vacation vocabulary.
2. The overpacking situation
Boomers do not believe in traveling light.
Their suitcases are packed to the brim with “just in case” items: backup outfits, extra shoes, a full pharmacy’s worth of medications, and maybe even their own travel-sized coffee maker.
You’ll be amazed at what emerges from their luggage.
Rain ponchos for a desert trip.
Formalwear for a casual beach resort.
Enough sunscreen to protect a small village.
While you’re trying to squeeze by with a carry-on, they’re happily checking two oversized bags—then reminding you that they’ll never understand how you manage to “travel with so little.”
3. The obsession with value for money
Boomers love a good deal.
On vacation, this translates into a near-constant focus on whether every meal, tour, or activity is “worth the price.”
They’ll scour restaurant menus for the best value, compare excursion costs down to the penny, and sometimes spend more time researching a deal than actually enjoying it.
Even when they splurge, they need to verbally justify it: “Yes, the dinner was expensive, but the portions were huge.”
It’s not about being cheap—it’s about feeling like savvy, responsible travelers.
You’ll hear the phrase “worth every penny” at least five times before the trip is over.
4. The never-ending travel commentary
Boomers have a lot of thoughts while traveling.
And they like to share them—all of them.
They’ll narrate every step of the journey: the flight, the hotel check-in, the local sights, the service at dinner.
Even mundane details are fair game.
You’ll get a running commentary on airport security, room layouts, and the quality of the hotel’s complimentary coffee.
Sometimes it’s funny.
Sometimes it’s exhausting.
But either way, silence is not on the itinerary.
5. The surprising attachment to routines
You might expect vacation to be a time for spontaneity.
Not for many boomers.
They often like to stick to familiar habits, even in unfamiliar settings.
This can mean eating breakfast at the same restaurant every day, taking a walk at the exact same time each morning, or insisting on dinner reservations at 6 p.m. sharp.
These routines provide comfort and predictability, which is especially important when traveling far from home.
For you, it might feel repetitive.
For them, it’s what makes the trip relaxing.
6. The strong opinions about meals
Dining with boomer in-laws can be a full experience.
They have clear ideas about what constitutes a good meal, and they aren’t shy about sharing them.
They’ll praise exceptional service loudly and criticize poor service just as loudly.
Menu analysis becomes a group activity.
There will be debates about portion sizes, the freshness of the bread, and whether the coffee was “hot enough.”
Even if you try to keep things light, mealtime often turns into a roundtable discussion worthy of a food critic panel.
7. The photo documentation marathon
Boomers love capturing memories.
But their approach to vacation photos can feel… intense.
Every landmark, every meal, every group shot must be carefully documented.
They’ll stop mid-walk to line everyone up for a photo, often taking multiple versions “just in case.”
Then comes the evening ritual of reviewing and sharing the day’s pictures, often complete with commentary and laughter over blurry shots.
By the end of the trip, you’ll have hundreds of photos—and a renewed appreciation for candid moments you weren’t even aware were being captured.
8. The fascination with hotel staff
Boomers tend to form quick bonds with hotel staff, tour guides, and restaurant servers.
By day two, they’ll know everyone’s name, backstory, and probably a few details about their personal lives.
They’re also generous with tips and heartfelt compliments, creating mini relationships wherever they go.
While you might be focused on your itinerary, they’re busy building connections that make the trip feel more personal.
This can be heartwarming—or slightly awkward when they start introducing you like you’re all old friends.
9. The unspoken battle over control
Every group trip has power dynamics.
With boomer in-laws, there’s often a quiet tug-of-war over who gets to decide what happens next.
They may expect to set the schedule, choose the restaurants, or dictate the day’s activities.
You, meanwhile, are trying to balance their preferences with your own desires—and keep the peace with your spouse in the process.
This negotiation isn’t usually dramatic, but it’s always there, humming beneath the surface like background noise.
And when handled well, it can actually become part of the fun… or at least a funny story later.
10. The bittersweet goodbye
When the trip ends, emotions run high.
Boomers often express their gratitude in heartfelt ways, thanking everyone for the memories and reminiscing about favorite moments.
They’ll also immediately start talking about the next trip, sometimes before you’ve even unpacked from this one.
For all the quirks and frustrations, there’s a sweetness in these farewells.
Because underneath the awkward moments and minor conflicts, these vacations are really about connection—creating shared stories that will be told for years to come.
And that part?
It makes all the chaos worth it.
The bigger picture
Traveling with boomer in-laws is a lesson in patience, humor, and perspective.
It forces you to see the world through different eyes and to navigate personalities you might not fully understand.
Yes, there are moments of tension.
Yes, there are times you want to hide in your hotel room.
But there are also unexpected joys—the laughter over dinner, the surprise bonding moments, the shared awe at a beautiful view.
These trips may not always be restful, but they’re rarely boring.
Closing thought
At the end of the day, vacationing with boomer in-laws is about more than logistics and schedules.
It’s about family dynamics, generational differences, and the stories you’ll laugh about for years.
Because while you may never agree on wake-up times or dinner reservations, you’ll always have those memories—messy, funny, and completely unforgettable.
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