Hey friends, it’s Lizzie! Let’s talk about the group chat that’s been “planning a trip” for the last two years and has produced exactly zero trips.
In your 20s, a girls’ trip happens because someone says “let’s go to the beach this weekend” on a Tuesday and by Friday you’re there. In your 30s, that same trip needs a spreadsheet, six calendars, someone’s PTO approval, and a small miracle. And I think that’s exactly why it matters more now than it ever did — the friendships that survive the logistics are the ones worth protecting.
Why It’s Harder to Make Happen (And Why That’s the Point)
Nobody warns you that adult friendship takes actual scheduling. Careers, partners, kids, distance — your people are scattered across time zones and responsibilities that didn’t exist a decade ago. A trip that used to take one text now takes a month of back-and-forth.
Here’s the reframe that’s helped me: the effort isn’t a sign the friendship is fading. It’s the cost of keeping something worth keeping. Easy things don’t need protecting. This does.
You Don’t Need a Big Production
This is the part that stalls most trips before they start — everyone pictures an expensive, multi-day production and it feels like too much to coordinate. It doesn’t have to be. Some of my favorite trips have been one night at a friend’s lake house, or a single afternoon on someone’s boat with everyone bringing a dish. The point was never the itinerary. It was getting everyone in the same physical space with their phones face-down for a few hours.
Lower the bar on purpose. A weekend away is wonderful, but a Saturday is enough to count.
The Group Chat Rule That Actually Gets Trips Booked
The trips that actually happen follow one rule in my friend group: whoever brings up the idea also brings three dates. Not “we should do this sometime” — three actual weekends, picked and dropped in the chat, first-come voting only. Open-ended planning dies in the group chat every single time. A trip with a deadline gets booked.
Second rule: someone has to own it. Not a committee, one person who books the thing and sends the Venmo request. Democracy is great for choosing a restaurant. It is terrible for booking a rental.
What We Actually Do When We’re There
Nobody needs a packed itinerary. My best trips have had almost no plan at all — water time in the mornings before it gets too hot, someone always ends up on a paddleboard with a guitar they half-remember how to play, watermelon cut up on the counter because it’s the easiest snack that feeds a crowd, and cards or a pool table at night if the house has one. The unstructured hours are the ones people actually talk about later.
If you’re local to the water like I am, a boat day folds beautifully into a girls’ trip — jumping off the back, floating, nobody checking a phone. I’ve written before about why boat days are non-negotiable for me, and they hit even better with the right people on board.
The Right Group Size (It’s Smaller Than You Think)
Bigger isn’t better here. A group of four to six is my sweet spot — small enough that one shared bathroom and one dinner reservation actually work, big enough that the energy doesn’t fall on one or two people to carry. Once you get past eight or so, you’re not really having one trip anymore, you’re running two or three smaller trips that happen to be under the same roof. If your real friend group is bigger than that, consider rotating who goes on which trip instead of trying to fit everyone into one house every time. Fewer people, more actual conversation.
The Prep That Actually Makes a Difference
You don’t need a packing list app for a weekend away, but a few things genuinely make these trips smoother. A shared note (not another group chat thread) for who’s bringing what — food, drinks, a speaker — so you don’t end up with five bags of chips and no ice. Confirm check-in and checkout times before anyone books flights or drive times around them. And if you’re anywhere near water, one dry bag for phones and wallets saves someone’s trip every single time. I’ve lost a phone off the back of a boat once. Once was enough.
It’s Okay to Say No to a Trip
Not every invite fits every season of life. Some years I’ve had the budget and the bandwidth for three trips. Other years, one was all I could manage, and that was the right call. A real friendship survives a “not this time, but I want the next one” — it’s the guilt-trip pressure to say yes to everything that actually wears friendships down. Protect your yes by being honest about your no.
The Real Return on Investment
I’m not going to pretend this is backed by a clinical study — it’s backed by every single time I’ve come home from a weekend with my closest friends feeling lighter than I have in months. Adult life doesn’t hand you connection, you have to build the container for it. A trip, even a small one, is one of the best containers I’ve found.
So take the L on the two-year group chat. Pick three dates. Send them today.
Somewhere to go next: why solo travel is better now.
Your Questions, Answered
How often should friends realistically try to travel together? There’s no magic number — once or twice a year is a realistic target for most busy friend groups, and even one solid overnight trip a year is worth protecting on the calendar.
What if everyone lives in a different city? Pick a rotating home base, or meet in the middle. A trip doesn’t need to be convenient for everyone to be worth it — it just needs a date that enough people can hit.
How do you handle the cost split fairly? Decide the split before booking, not after. One person fronting a rental and Venmo-requesting everyone else immediately avoids the awkward math (and the resentment) that shows up later.
Now tell me, friends: when’s your next trip with your people? Drop the destination (or the group chat status) in the comments. And come hang out with me on Instagram @sealillly for more real-talk lifestyle finds. Love you, mean it. ✨
