How many times have you said it?
“Someday we’ll take that girls’ trip.”
“We really need to plan a weekend away.”
“Next year for sure.”
“Someday.”
And then someday never comes.
Because life gets busy. Kids need care. Work gets intense. Money feels tight. Coordinating schedules feels impossible.
So you keep saying “someday” while watching everyone else on Instagram take their perfect friend trips.
And you wonder: Why can’t I make this happen?
Here’s what I want to tell you: You can. But probably not the way you think.
The Instagram Trip That’s NOT the Standard
I just got back from an 11-day road trip with my friend Kalin.
We drove from New Orleans to Indianapolis. We saw Taylor Swift twice (yes, really). We explored random cities. We had zero plans. We worked from hotel rooms. We ate Trader Joe’s snacks in the car.
And if you saw it on Instagram, you might think: “Why can’t I do that?”
Here’s why: Because it’s not normal. At all.
That trip happened because of a very specific set of privileges and circumstances:
We’re both childless. No arranging care for 11 days. Just making sure Kalin’s husband fed her cat.
We have money. 11 days adds up, even when you’re staying at Spring Hill Suites and eating simple meals. We could afford it.
We have time flexibility. We’re both self-employed. We worked on the trip, but we could take 11 days without asking for PTO.
We got incredibly lucky. We randomly got Taylor Swift tickets through a Capital One drop. Decided to road trip one month before. Stars aligned.
This is not a replicable model for most people.
And honestly? I don’t know if I’ll ever be able to do something like that again.
But you know what? I’ve taken dozens of other trips with friends that WERE replicable. That you absolutely can do.
And that’s what I want to talk about today.
My New Goal (And Why It’s Realistic)
Here’s something that happened on that road trip:
We were sitting in Nashville, and I had this realization: I want to take a one-week girls trip.
Not 11 days. Just one week.
With multiple friends. Somewhere we can all get to. Where we can actually relax and connect.
And you know what my timeline is for making that happen?
The next decade.
A DECADE.
You might think that’s ridiculous. Why so long?
Because I’m being realistic.
Getting multiple friends to:
- ▪️ Save enough money
- ▪️ Arrange childcare for a week
- ▪️ Coordinate PTO
- ▪️ Align schedules
- ▪️ Agree on a destination
That takes time. Especially as we all get older and our lives get more complex.
So I’m giving it a decade. And I’m starting to talk about it NOW.
I’m asking friends what’s feasible. What they’d want to do. Where they’d want to go.
Because if I wait for the perfect moment, it’ll never happen.
But if I start planning now, give it time, and stay flexible?
I think we can make it happen.
And in the meantime? I’m not waiting. I’m taking smaller trips. Doing local things. Making it happen, however I can.
Because here’s the truth: You don’t need an 11-day road trip to connect with your friends.
You just need to stop saying “someday” and actually put something on the calendar.
Here’s how.
TIP #1: Start Small (Like, Really Small)
I know it’s tempting to plan the dream trip.
The all-inclusive resort. The European adventure. The week at a beach house.
And maybe someday you’ll do that. But don’t wait for that to make something happen.
Start with something so small it feels almost silly.
Because here’s what I’ve learned: Small trips build momentum.
When you actually get together (even for just a night) everyone remembers how fun it is. How good it feels to be together.
And then they’re way more likely to prioritize the next one.
Example: The Trader Joe’s Sleepover
About a year and a half ago, a bunch of us decided to have a girls’ night.
Not a fancy trip. Just a sleepover at my friend Brooke’s house.
Her husband was out of town (though we probably would’ve kicked him out anyway). We all showed up in our sweatpants.
And here’s what we did for our “big adventure”: We went to Trader Joe’s.
Five or six of us, plus Brooke’s daughter, wandering through Trader Joe’s with a cart.
Our rule: Buy anything you’ve ever wanted to try but never had a reason to.
That random appetizer. The fancy crackers. The weird dip. The dessert you’ve been curious about.
That was our dinner.
We went back to Brooke’s, cooked it all up, ate on the floor, did bedtime stories with her daughter, slept in guest rooms, and on couches.
Woke up the next morning, made breakfast, went for a walk, drank coffee.
Everyone went home by noon.
And you know what? That’s one of my favorite friendship memories.
Not because it was fancy. Not because we went anywhere special.
Because it was easy. And fun. And we actually did it.
Other Small Trip Ideas:
Local staycation: Rent an Airbnb in your own city for a night. Or a local hotel. Or borrow a friend’s vacation home.
Day adventure: Pick a local event or attraction. Make a whole day of it. Bring snacks. Make it special.
Virtual experience: Can’t get together in person? Take a virtual cooking class together. Do a series of something. Start a regular virtual book club or game night.
Weekend nearby: Don’t fly. Drive somewhere 2-3 hours away. One night. Low stakes.
The point: Rip the band-aid off. Get SOMETHING on the calendar.
Even if it’s just a local sleepover where you go to Trader Joe’s.
Because once you do it once, everyone will want to do it again.
TIP #2: Give Everyone Time (Like, A LOT of Time)
Here’s something we used to do when we were younger and childless:
Decide on a trip like two months out. Book it. Go.
That doesn’t work anymore.
Now? We book trips a year in advance.
Example: Some friends and I are planning a girls’ trip in January.
We picked the date in June.
Six months’ advance notice. And we STILL haven’t booked flights or hotels.
But the date is set. Everyone knows. Everyone’s arranging their lives around it.
Why so far out? Because one of the friends coming is a mom to a medically complex kiddo.
She needs time to arrange nursing care. To coordinate schedules. To make sure everything’s covered.
And honestly? Everyone needs time now.
What Time Allows:
Money: If the trip is a year out, you can save $50-100/month instead of scrambling to find $1000 all at once.
Childcare: You can coordinate with family, trade with other parents, research local services, and plan way in advance.
PTO: You can request time off early, before everyone else claims the good weeks.
Life logistics: You can work around other commitments instead of trying to squeeze it in.
Mental preparation: You can actually get excited instead of stressed.
But What If It Falls Through?
Here’s the beautiful thing: Even if a trip you planned a year out doesn’t happen, you’ve learned what you need to make it work.
So, when you set the next date, six months or a year later?
You’re all more prepared to actually pull it off.
The planning itself teaches you what’s feasible. What’s realistic. What everyone needs.
So just set a date. Even if it’s far out. Even if you’re not sure it’ll work.
Put it on the calendar and see what happens.
In the full episode, I share even more stories from friend trips that almost didn’t happen and what finally got them on the calendar. If you’ve been saying “we should do a trip” for years, but it never materializes, this episode will give you the push (and the practical framework) you need.
TIP #3: Focus on Connection, Not the Perfect Vacation
This is the one that I think trips people up the most.
We think: If I’m going to arrange childcare, save money, take PTO, and coordinate schedules… it better be PERFECT.
It better be the African safari. The European cruise. The Instagram-worthy adventure.
But here’s what I want you to hear: That mindset is keeping you from going at all.
Because if the bar is “perfect vacation,” you’ll keep waiting for the right time, the right budget, the right circumstances.
But if the bar is “quality time with people I love”? That you can do anytime.
What This Actually Looks Like:
Most of my favorite friend trips look like this:
We rent a house. We plan ONE activity per day. Maybe.
We order groceries delivered to the house. We split up cooking duties (and usually cook together. It’s bonding time).
And then we just… exist together.
Lying by the pool. Going for walks. Exploring the local area on a whim. Watching a show. Taking naps.
Lots and lots of time to just talk. And be. And connect.
No packed itinerary. No rushing from attraction to attraction. No stress about hitting all the must-see spots.
Just presence.
Why This Is Better:
It’s cheaper. You’re not paying for expensive activities, fancy restaurants, or constant entertainment.
It’s more accessible. More people can afford it. More people can participate.
It’s actually restful. You’re not coming home exhausted from running around for four days straight.
It’s what you actually need. You’re not there to see the sights. You’re there to see each other.
And It Doesn’t Even Require Travel:
This could be a local staycation. Someone’s house. A borrowed vacation home.
You don’t have to get on a plane to connect with your friends.
I talk through even more creative, low-pressure trip ideas in the complete episode, including how to handle the awkward money conversations and what to do when someone drops out last minute. Listen here for the full breakdown.
Stop waiting for the perfect, Instagram-worthy vacation.
Start prioritizing actual connection. However, that looks.
TIP #4: Work on the Details Together Upfront (Planning IS Bonding)
Here’s what usually happens with group trips:
Either one person does ALL the planning (and gets resentful).
Or NO ONE does the planning (and it’s a scramble at the end).
I want to suggest a different approach: Make the planning part of the experience.
How This Works:
Let’s say you set a date for a year from now.
Great. Now you have a year of reasons to connect.
Month 1: “Hey, if we were staying on the West Coast, what areas would everyone want to explore?”
Text thread starts. Ideas flow. You’re already connecting.
Month 3: “Okay, we’ve narrowed it to three cities. What activities sound fun? What restaurants?”
Everyone throws out ideas. You’re learning what people value. What excites them.
Month 5: “The budget’s getting intense. How can we make this more accessible?”
Problem-solving together. Combining forces.
Month 7: “Who’s good with credit card points? Can we hack some of these costs?”
Sharing knowledge. Teaching each other. Bonding over figuring it out.
Real Example: The Money-Saving Apps
On my road trip with Kalin, she’s the queen of money-saving hacks.
At one point she’s like: “Oh, we can get this dinner for a third of the price if we use this app.”
I’d never heard of it.
She taught me. We used it. We saved money.
That became part of the trip story. Part of our connection.
If she’d just handled all the planning alone, I wouldn’t have learned that. We wouldn’t have had that moment.
Combining Forces on Childcare:
This is where group planning really shines.
If childcare is the big obstacle, get creative TOGETHER:
Can someone bring a family member who could watch multiple kids?
Is there a local service you could split the cost of?
Do you know anyone in the area who could help?
Can you trade childcare with other parent friends? (You watch their kids one week, they watch yours during your trip?)
When you problem-solve together, you’re not just planning a trip. You’re proving to yourselves that you CAN make this happen.
And that makes the actual trip so much more meaningful.
Because you’ll look back and think: “We really did that. We made it happen together.”
The Social Media Reality Check
I need to say this again because it’s important:
Social media is a highlight reel.
You see my 11-day road trip. You don’t see the months I spent in bed with health issues before it.
You see the perfect sunset photo. You don’t see us working until midnight in the hotel.
You see the fun concert moment. You don’t see the privilege that made it possible.
Please don’t compare your life to anyone’s Instagram.
And please don’t let seeing other people’s “perfect” trips make you think your simple weekend getaway doesn’t count.
It counts. It all counts.
The local sleepover counts. The day trip counts. The staycation counts.
Any time you prioritize connection with your friends, it counts.
What to Do Right Now
If you’ve been saying “someday” about a friend trip, here’s what I want you to do:
Pick ONE of these tips and do something about it THIS WEEK:
Option 1: Start Small
Text your friends right now: “Want to do a sleepover at my place next month? We’ll go to Trader Joe’s and make it an adventure.”
Set a date. Keep it simple. Make it happen.
Option 2: Give Time
Text your friends: “I want to plan a weekend trip for next [season/year]. Let’s pick some dates now so everyone can plan around it.”
Just get dates on the calendar. Figure out details later.
Option 3: Shift Your Mindset
Stop waiting for the perfect trip. Start thinking: “What’s the easiest way for us to get quality time together?”
Then do that.
Option 4: Start Planning Together
If you already have a trip on the calendar, start a group text: “Okay, let’s start brainstorming. Where do we want to stay? What do we want to do? What’s everyone’s budget?”
Make the planning part of the fun.
My Challenge to You
I’m going to be honest: I don’t know if my one-week girls’ trip will happen in the next decade.
Life is unpredictable. People’s circumstances change. Things come up.
But I’m going to try. I’m going to keep talking about it. I’m going to keep planning.
And in the meantime? I’m going to keep doing the smaller things.
The weekend trips. The local sleepovers. The day adventures.
Because I’d rather have 10 small trips than keep waiting for one perfect trip that never happens.
So here’s my challenge to you:
Stop saying “someday.”
Pick something (anything!) and put it on the calendar.
Even if it’s just a Saturday afternoon picnic in the park.
Even if it’s just one night at a local hotel.
Even if it’s just a virtual cooking class together.
Make something happen.
Because here’s the truth: The perfect trip you’re waiting for? It’s not coming.
But the imperfect trip you actually take?
That’s the one you’ll remember forever.
Been saying “someday” about a friend trip for years? What trip are you dying to take? Drop it in the comments below?
Want to see the 11-day road trip that inspired this post? Check out my Instagram highlights. It’s saved under “Eras Road Trip” 🚗 But remember: that’s NOT the standard. Don’t compare yourself to it. Just let it inspire you to make SOMETHING happen, however small.
Want all four tips in detail, plus bonus stories from my own friend trips? Tune into the full episode for everything I couldn’t fit into this post, including the behind-the-scenes of planning a trip with 8 people across 4 time zones.
