Starting off strong, but it needs to be said:
Tip #1: Really think about if you want to be in the same house as everyone in the group for an extended period of time.
If yes, float a trip to the group! Some groups are meant for just afternoon/evening hangs, others can do multi-day trips together. Neither is better than the other, just different kinds of hangs.
I sang in choirs for most of my life and wanted to continue college (thanks to a strong-arm from one of my best friends in high school who was already in the Chorus). At the end of my pre-orientation backpacking trip, I met another freshman who was on the fence about joining the Chorus, the counterpart to the choir her older brother was in. According to her, my enthusiasm made her lean more towards actually doing it. In my eyes, she was the coolest outdoors-y person that SO many people knew and loved and I immediately wanted to be her friend. That's how I met Stef (my very first college friend™) and an invisible web started weaving. Once we both got into the group, we met Marissa, the future president of the Chorus with an unmatched level-headed-ness. We awkwardly found our way together, between rehearsals, walking back from parties, and meeting up for dinner.
A year later came the second half of our group: Sarah, the same year as Stef, Marissa, and I, who was set to change the world of infectious diseases; Christina, the brilliant bookworm on track to become a powerhouse attorney; and Sydney, wonder personified who was obsessed with sharks. None of us had the same major, rarely shared classes, and were on completely different paths. We became the Chicks (spoof off of where we lived together senior year) and supported each other through the wild twists and turns of college and adult life.
Graduation eventually came for the Chicks. Sydney and Christina were the year behind the other four of us, and the graduates scattered across the country. Our group chat went silent, not because we didn't love each other anymore, but life has a way of not stopping. We moved cities and states, continued our education, and advanced in our careers. We were busy doing what our younger selves had dreamed of.
Then, I got married. My husband and I had met through the choirs, so all of them knew him for as long as I did. We asked our choir friends to sing at our wedding, and I (naturally) put the Chicks all together at a table. I was off doing married things, but the ember reignited around their table. Sydney mentioned her dad Scott would go on an annual trip with his college friends when she was growing up. If he did it while raising kids, why couldn't we?
Tip #2: Planning a group trip needs a leader, ideally someone familiar with where you're going (or willing to do the research).
This person doesn't need to do it all (delegate!) but someone needs to take charge for it to happen.
I got married in 2023 but our first trip didn't happen until 2025. We were all still busy but didn't know how to get started. Eventually, Sydney started a monthly call, and through that, we started planning. We picked a date, picked a place (my parents’ beach house) and held our breath.
Planes, trains, and automobiles, but we all got to the Jersey shore in one piece. Since we were at “my” house, I took charge of planning our meals and activities. I balanced dietary restrictions with mixed success (I'm still sorry for your janky grilled pizza, Marissa, I learned my lesson).
Tip #3: Identify a purpose for the trip, beyond just “it’d be fun.”
When you identify the purpose, you can plan the trip intentionally. Want to see a new place? Plan an itinerary with stops listed out (and check with the group of how much you want to do). Want to catch up? Plan to relax where you're staying more with some games/activities to break up the gab sessions. Is it a last hurrah before someone moves? Try doing a tour of where you currently are to get one last taste of everything.
Sydney was getting married two months after the trip but didn't do a traditional bachelorette party. We still wanted to celebrate her, so we threw her a surprise bachelorette night with a behind-the-scenes tour at the aquarium (it was technically meant for children but put 6 curious nerds on a tour and we're happy as can be).
We relaxed on the beach, played board games, and laughed like we hadn't in years. We did the unimaginable: we got the trip out of the group chat. Year 1 was complete.
Tip #4: The first year is a one-off trip. If you want to make it a tradition, you need the second time.
Another friend told me that it takes two years for something to be a tradition, so I knew this year would be crucial to lock it in.
Sometime in late spring this year, the same texts started to make their rounds in the group chat “So…. Chicks Trip??”
Since we had such a blast at the beach last year, we figured we would just do it there again. We planned around PTO, parental leave, holidays, starting new jobs, and what weekends were even still free at the beach. People booked flights and trains, and I built out a monster spreadsheet to mark down exactly what we needed. We were so ready.
Tip #5: Stay flexible.
Mother Nature doesn’t care how excited you are.
Ready or not, the September 2026 Nor’easter had other plans for us. The first stage was accepting we likely wouldn't get any time actually on the beach. Then, it became a question of if it was even a safe idea to go. The house is on one of New Jersey’s barrier islands, an area VERY prone to flooding.
The morning we were supposed to go down, I decided to change our plans. Flights and trains couldn't be changed (by us), but everyone was “landing” only 30 minutes from my house. New plan: everyone stays with me!
Thankfully, I'd been keeping an eye on the weather the days before and decided to buy groceries at home instead of waiting until I got down there. I like to keep my house “hang-out ready” with a stocked pantry, paper plates and foil trays on deck, and tidy-able in 30 minutes (not not clean, but I'm not scrubbing walls on the regular). We have two beds, an air mattress, a pullout, and a pretty comfy couch. Between blankets and pillows people brought and we had, we would make it work.
Tip #6: If you’re the leader, guide the trip like a moderator, not a cruise director.
You’re meant to be part of the gathering, not waving the umbrella for the tour to follow.
With such a last-minute change, I started panic-texting the group some activity ideas: Axe throwing? Farmers market? Movie?
But we didn't end up booking anything. What we actually did was so much more fulfilling: we engaged with each other. Since people trickled in, we wrote down a list of things to talk about when we were together (and yes, actually on a pad and paper. It wasn't specified to keep our phones away, but it naturally happened anyways).
A cruise director keeps things moving down to the minute, operating on a separate level from the group. They're not meant to be participating in the activities as much as setting the experience. A moderator is immersed in the experience, guiding from within based on what's happening. They're engaged and participating: an active member of the group. After too many occasions of acting as a cruise director, I finally learned how to tell when we were ready (instead of “when it was time”) to move into the next thing. It takes practice.
We talked through new and old relationships, parenthood, careers, our mental and physical health, and so much more. We played silly games, went for a walk in our sweatpants, made hibachi at home, and decorated homemade mini cakes.
Tip #7: Don't do the trip for the post; do it for the memories.
If your group is like ours, this trip likely is the only time you see each other all year. Act like it.
We went from seeing each other every single day in college to seeing each other once a year, if we're lucky. We didn't say it out loud to keep our phone use to a minimum, but it happened. Even though I knew I would want to write about the weekend, I barely captured any content because I was just enjoying myself. Make it a point to be present with each other. You’ll be so happy you did.
