The Delicate Art of Group Travel — and Why Even Apple Can't Fix It

The Delicate Art of Group Travel — and Why Even Apple Can't Fix It

As adults, we learn that friendships exist in compartments: the confidant who knows your family secrets isn't always the one you'd invite to a raucous party, and the roommate you shared a studio with might vanish from your life the moment the lease ends. But the most elusive bond? The friend who can survive a trip with you. Over time, my list of travel-compatible companions has dwindled to near-zero — I'd rather wander solo than risk a group implosion.


Group trips, as many have learned the hard way, are a minefield of unspoken expectations. Sharing a cramped Airbnb or debating who owes $4.50 for gas reveals sides of people you can't unsee. While some relationships emerge stronger, others unravel entirely — which is why Apple's new group-planning tool, Apple Invites, caught my attention. Promising to streamline itineraries and centralize communication, the app syncs trips with your Calendar and Weather apps, lets hosts draft 1,000-character itineraries, and even auto-generates shared playlists and photo albums. No more chasing down that one friend who never shares their snapshots.


Yet for all its polish, Apple Invites sidesteps the two biggest trip-wreckers: money and control. There's no feature to split expenses, leaving users to juggle Splitwise and Venmo — or, in my case, quietly hope no one notices my growing tab of unpaid coffees and train tickets. Worse, only the host can edit plans, a design that either empowers your group's hyper-organized "planner friend" or sparks mutiny among collaborators. (Pro tip: Just use a Google Doc.)


Still, Apple's ecosystem might be the app's saving grace. Like it or not, their devices already dominate our lives — phones, watches, streaming — and centralizing plans in one place beats the chaos of fractured group chats and lost Instagram DMs. After testing it for a summer trip to Montreal, I'll admit: The convenience outweighs my resentment at being funneled deeper into Apple's walled garden. But until it solves the real problems — who's paying for the Airbnb rug someone definitely stained — even Silicon Valley can't salvage the group trip. Some bonds, it seems, are best left untested.

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