For the Friend Who Always Plans the Trip (Yes, You)

Welcome back to the Where.App newsletter! This one's for the designated trip planner in every friend group.

Jul 30, 2025

Let's be honest – part of you loves being the designated trip planner. You get a thrill from discovering the hidden gems. You enjoy the puzzle of fitting experiences together into a cohesive day that flows naturally from morning coffee to evening cocktails.

But then reality hits.

Research shows it takes the equivalent of two full work days, or 16 hours, to plan and book a trip, with Gen Z and Millennials spending an additional 30% more time. What starts as exciting research quickly becomes an overwhelming responsibility.

The joy of discovery gets buried under the anxiety of logistics. You love curating experiences, but you hate being responsible for everyone else's good time.

Three Major Planning Pitfalls That Kill Great Trips

The Research Rabbit Hole: You dive deep into reviews and travel blogs, spending hours analyzing whether a restaurant is "actually good" or just tourist-friendly and then doing the guesswork of whether reviewers share your group's preferences and quality expectations.

The Timing Trap: You create minute-by-minute schedules that look perfect on paper but fall apart in reality. In Rome, your 10 a.m. arrival at the Leonardo da Vinci airport and 12 p.m. Colosseum slot seem doable - until baggage claim, passport lines, and a 40-minute ride to the city center throw everything off.

The Local Knowledge Gap: You rely on generic travel content created for mass audiences, missing insider knowledge that prevents the disappointment of closed doors and long lines. You saved your last day in Paris for the Louvre - only to find it closed. Like many French museums, it's shut on Tuesdays, something local guides know and generic blogs often skip.

Travel Expert’s Advice

Here's what travel industry experts recommend for smoother group planning: Set up a group chat early and maintain centralized communication throughout the planning process to reduce confusion. Plan early, define everyone's expectations upfront, and delegate specific tasks to group members. Book travel early to secure group rates and ensure adequate space for your entire party. Create itineraries that balance group activities with free time, allowing people to explore individually or split into smaller groups.

How Where App Solves Real Planning Problems

Where App solves these problems by changing how you discover and organize experiences:

The personalized curated feed of real experiences from locals and seasoned travel creators allows you to skip endless Google searches. See actual photos and discover experiences that match your group's vibe.
Local intel access connects you directly with people who live in your destination and regularly travel with groups. Get insider timing, crowd patterns, and logistics that generic travel content misses.
Visual route previews show exactly what to expect, eliminating the guesswork that causes group conflicts and last-minute scrambling.
Wherebot, your personal AI assistant, learns your planning style and handles the tedious research parts, so you can focus on the creative discovery you actually enjoy.

Just chat with it like with a friend, and it will help you like a trusted travel advisor would.

Instead of starting from scratch every time, you access tested local expertise. Wherebot learns from real movement data and local creator knowledge, understanding that "best brunch spot" means different things for a bachelorette party versus a family with toddlers.

Ready to Plan Like a Pro?

Where App doesn't replace your curatorial instincts – it amplifies them with local expertise and intelligent assistance, so you can focus on what you love about planning while reducing the stress that makes it feel like work.

👉 Sign up at where.app or email founders@where.app saying “Beta”!

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