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December 15, 2025

Why We Built This Group Trip Planning Tool

Discover how Calendude evolved from chaotic group chats to spreadsheet headaches to the simple group vacation planner you need to plan vacation with friends.

You know that moment when someone throws out "we should totally take a trip together!" in the group chat? Everyone gets excited, drops a bunch of fire emojis... and then the planning begins.

And that's when things get messy.

Group chat planning chaos with scattered messages about travel dates The all-too-familiar chaos of planning trips in group chats

How We Used to Plan Group Trips

I've been there more times than I can count. What starts as excitement quickly turns into scrolling through endless messages trying to figure out who said they were free in March versus April. Someone inevitably asks "wait, what dates are we talking about again?" three days after you already discussed it.

We tried planning trips in group chats for years. WhatsApp, Messenger, Discord - you name it. The problem? Important details get buried under memes and random conversations. Good luck finding that message where Sarah mentioned she couldn't do weekends in February.

The Google Sheets Phase

Eventually, we got smarter (or so we thought). Someone would create a Google Sheet with everyone's names and dates, and we'd mark when we were available with little X's or checkmarks.

Google Sheets template for group trip availability tracking A typical Google Sheets setup for tracking group availability

Honestly? This worked way better than the group chat chaos. At least now we could actually see everyone's availability in one place.

But here's the thing - not everyone is comfortable with spreadsheets. My friend Jake took like 20 minutes to figure out how to edit the sheet on his phone. And once we narrowed down the dates, we still had to manually search for flights and hotels, compare prices, and paste links back into yet another tab in the sheet.

Plus, Google Sheets has its limits. What about actually booking stuff? What about seeing which dates give you the best flight and accommodation prices? The spreadsheet could only take us so far.

Why We Built Calendude

After one too many trips where coordinating dates felt like a part-time job, I thought: there has to be a better way to plan vacation with friends.

That's why we created Calendude as a group travel planner. It takes everything that worked about the Google Sheets approach - seeing everyone's availability clearly laid out - and adds the stuff we were missing:

Calendude interface showing group availability calendar Calendude's clean interface makes tracking group availability effortless

No learning curve. Your friends don't need to understand spreadsheets or formulas. They just click the dates they're available. Done.

Smart suggestions. Instead of manually counting who's available when, Calendude shows you which dates work for the most people at a glance.

Built-in search. Once you've narrowed down your dates, you can search for flights and accommodations right there. No more juggling between 47 browser tabs.

Everything in one place. Availability, date selection, flight options, hotel links - it's all there. Your group chat can go back to what it does best: sharing terrible travel memes.

Planning Group Trips Shouldn't Be a Headache

Look, I'm not saying Calendude is magic. You still need to actually coordinate with your friends (good luck with that). But at least now you've got a trip date planner that makes it easier to find a date that works for everyone and actually book the trip.

Because at the end of the day, the hard part should be choosing between Thailand and Portugal, not figuring out if everyone can make it the second week of June.

Ready to plan your next group trip without the spreadsheet headaches? Get started with Calendude and see how it works, or read our guide on finding the cheapest time to travel as a group.

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