What I Learned Trying to Plan a Trip With 5 Friends and 300 Texts
Planning a trip with friends should be exciting. Beaches. Aperol. Group selfies. Instead, it felt like I was producing a Broadway show with no script, five directors, and a budget written in disappearing ink.
Here’s what actually happened, and what I’ll never do again.
📱 1. The Group Chat Is Not a Planning Tool
We started with a group text.
It seemed easy enough:
“Guys let’s go somewhere in July.”
48 hours later, we had:
- 7 destinations
- 14 different travel dates
- 3 competing ideas about “vibe”
- And a rogue link to a goat yoga retreat in Vermont
None of it was tracked. None of it was final. Every new message buried the previous five.
Lesson: Group chats are great for memes, not logistics.
📆 2. Calendars Matter More Than You Think
Turns out, “July” is vague.
One person could only do early July. Another was traveling mid-July. And one brave soul hadn’t even opened their calendar app yet. We only realized the overlap after 30 texts and a Google Sheet.
Lesson: You need a visual calendar from the start. Something that helps people see overlap without a spreadsheet that looks like a tax return.
🗺️ 3. No One Wants to Be the Planner (But Everyone Has Opinions)
I somehow became the de facto trip planner.
I didn’t volunteer. I just asked one too many questions.
Suddenly I was in charge of:
- Finding flights (that matched 5 departure cities)
- Booking an Airbnb (that didn’t look like a murder house)
- Creating “options” for each day
- And somehow not offending anyone in the process
Everyone had feedback. No one wanted to make decisions.
Lesson: Decision fatigue is real. Shared planning tools help distribute the load, and the blame.
🤯 4. Memory Is a Lie
By week two, we had so many links, screenshots, and messages that no one remembered what we’d actually decided. One friend booked a flight for the wrong weekend. Another thought we were staying in Positano, not Sorrento.
Lesson: You need a single source of truth. Ideally not your memory or your phone’s photo gallery.
🧠 5. Next Time, I'm Using a Tool Built for This
After surviving the textpocalypse, I finally found a better way: Plan Harmony.
It's made for exactly this kind of chaos:
- Organize your trip across days and cities
- Add flights, hotels, and activities in one place
- Collaborate with friends without losing your mind
- See gaps, conflicts, and overlaps clearly
- Actually feel like you're planning something... together
We now use it every time we travel as a group. No more 300 texts. Just a plan that makes sense.
✈️ TL;DR
Group trips are fun. Planning them without a proper tool is not. Don’t be the hero with a dozen tabs open and 14 chat threads to manage.
Use something that’s built for how travel actually works.
👉 Try Plan Harmony for your next trip
