Why I’m Now Hosting Group Trips (and Why It Matters)

Behind The BrandTravel Planning TipsMomcations Blog
Written By ~ Jillian ~

For years, I took an annual Momcation—just me (sometimes with a friend), a packed bag, and a few glorious days of freedom.

No guilt. No planning around nap schedules or snack preferences. Just real connection, rest, and a little adventure.

And every time I’d post a photo or share a story from those trips, I’d get the same messages from other women:

“I wish I could do that.”
“That looks amazing—I need something like that.”
“I don’t have anyone to go with.”

So I started helping. I gave tips. I sent links. I helped friends and strangers map out their own Momcations. And while some of them went… many still didn’t.

Because planning it yourself is overwhelming. Because rallying a group via group text is like herding cats. Because going solo sounds empowering in theory—but intimidating in real life.

Styled travel message overlay on a poolside background. Text reads: “I’ve been wanting to take a trip for myself, but I don’t have anyone to go with—and I honestly don’t want to plan it all. Do you ever let people just come along?”

That’s when I realized: these women don’t just need information—they need invitation.

That’s when Momcations went from an idea to a movement.

From “You Should Go” to “Come With Me”

Let’s be honest—planning a trip is a lot. Booking everything, making sure it's safe, coordinating schedules… and then there's the real kicker: figuring out who the heck you're going to go with.

Because as much as we dream of a break, the reality is a lot of women feel awkward going solo—and even more frustrated trying to rally friends who “totally want to do it!” but never actually book the trip.

I kept hearing the same things over and over:

  • “I don’t have anyone to go with.”

  • “I want to do more than sit at a resort and drink for 4 days.”

  • “I wish I could just tag along with your trip.”

And honestly? Same. I want more than cookie-cutter vacations.
I want a mix of fun and meaning. Spa days and sightseeing. Time to connect and space to exhale.

These women want exactly what I want:

  • A chance to see the world without dragging the whole family

  • Experiences their partner would hate or their kids are too young to enjoy

  • Freedom to do something for them—without having to compromise or coordinate with a dozen other people’s needs


Woman sitting solo on a lawn chair in Newport, RI during a weekend Momcation getaway.

So I thought, what if I could just say…

“Come away with me.”

Why Hosted Trips Work (and Why They’re Different with Me)

Now, I’m not reinventing the travel wheel. Group trips have existed forever. But let’s be real: a lot of them feel like you’re being dragged through a checklist with 48 strangers, being fed the same script and shuffled from one tourist trap to another.

That is not what we’re doing here.

My hosted trips are small. Intimate. Real.

I want every woman to feel like she’s part of something—not just a plus one. Whether you come solo or with your best friend, you’re part of the crew.

These trips are built for:

  • Connection, not cliques

  • A little adventure mixed with a lot of intention

  • Women who are ready to get out of the group chat and into the world

You don’t have to plan. You don’t have to explain. You don’t even have to know anyone. You just have to show up.

I’ll take care of the rest.



What’s Coming (And How to Join)

Here’s a peek at the upcoming hosted Momcation trips:

Grid of upcoming Momcation destinations: Savannah, Quebec, Santa Fe, and Ireland

  • Quebec City, QC – December 2026
    Twinkling lights, French flair, Christmas markets, and cozy winter magic.

  • Santa Fe, NM – March 2027
    Desert renewal, spa mornings, jewelry-making workshops, and a spring equinox reset you didn’t know you needed.

  • Ireland – October 2027
    Green hills, warm pubs, and staying in a literal castle. Come get your main character moment.

And more in the works...

These trips aren’t for everyone. They’re for the women who are ready to say yes.
Not someday. Not maybe. Not “if my friends want to go too.”

Just… yes.



So Consider This Your Invitation

Flat lay of a packed suitcase, sun hat, and travel essentials for a Momcation trip.

If you’ve been watching from the sidelines, wondering if something like this could be for you—this is your sign.

If you’re waiting for the right moment, or the right person to go with, or the stars to align—this is your moment.

I’m not here to pressure you. I’m just here to invite you.

So go ahead. Come away with me.
The adventure (and the rest, and the laughter, and the reset) is waiting.

Until next time, here’s to making time for yourself - you deserve it!

~ Jillian

#Momcations #MomsNeedBreaksToo
#ComeAwayWithMe #WomenWhoTravelTogether
#SoloButNotAlone #ConnectionOverChaos

~ Jillian ~
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School’s Out… and So Am I