5 Reasons Group Trip Planning Always Goes Wrong (And What to Do Instead)
Why DIY Group Travel Planning Is Harder Than Ever in 2025
You know the scene: your group chat has 47 unread messages about the upcoming trip, someone just sent their third TikTok link of the day about 'hidden gems,' and you're somehow stuck playing travel planner, accountant, and group therapist all at once.
Group travel has exploded in popularity over the last few years as people prioritize experiences over things and seek to reconnect in a post-pandemic world.
With 1 in 5 travelers planning group trips in 2025, more people than ever are discovering what expert travel planners know: DIY planning is a recipe for stress, hidden costs, and unexpected disappointments.
The average person spends 20+ hours researching a single trip—before dealing with payment collection, personality management, and budget coordination for multiple people.
According to Priceline, almost "40% of Gen Z believe less time dedicated to planning and booking would enable them to get into vacation-mode feeling energized, rather than starting their trip exhausted."
Here are the 5 biggest reasons why planning your own group trip becomes overwhelming—and what smart travelers are doing instead.
Reason #1: AI and Google Can't Curate Authentic Local Experiences
The Problem with Online Research for Group Activities
It’s true that booking travel, from flights to hotels, is easier than ever before. For many popular destinations, one Google search results in thousands of options, including how-to tips and endless tours and activities to book.
While it’s not impossible to book group travel alone, it isn’t necessarily straightforward, especially in places like Ghana, where local connections are still crucial because the most authentic local experiences aren’t on Google or social media.
Why Local Connections Matter More Than Search Results
With the rise of AI, using ChatGPT to plan your next group trip is likely tempting, but again, ChatGPT doesn’t personally know about the website-less (but so fun) cocktail-making class available in Accra.
In Rio de Janeiro, AI may tell you to go to Pedra do Sal for a locally-loved samba party held every Monday, but it doesn’t know where the best Black-owned capirihana stand is that you should absolutely stop at along the way.
While online research may work for solo or couple trips, making group trips unforgettable requires more time, consideration, and insider access.
Reason #2: Coordinating Multiple People Can Be A Logistical Nightmare
Managing Group Dynamics
Even for close friends or families, coordinating multiple people’s time, budget, availability, and personalities is never easy. Regarding birthday or bachelorette trip planning, groups tend to include six or more travelers, all with unique preferences and abilities that must be considered.
Dietary Restrictions and Budget Considerations
DIY group travel planners often overlook dietary restrictions, which could be life-threatening if the planner and attendees are not aware of someone's allergies or restrictions. For example, if someone has a seafood allergy, that should be taken into account from step one of planning the itinerary.
Beyond that, group travel budgets require more budget considerations than a solo or two-person trip. There are more people, payments, and ultimate budgets to remember when planning.
Extra care and attention are required to ensure the math is mathing.
Reason #3: Payment Collection Becomes Your Second Job
The Venmo and Zelle Chase Game
Collecting money for group travel payments is one of the most common pain points with group travel planning. For the group planner, chasing payments can get overwhelming, with so many people having various due dates and amounts.
Not only do they have to collect the money, but they’ll also have to track who paid, send payment due date reminders, and safely store the money until it’s time to make bookings on behalf of the group.
Why Manual Payment Systems Fail
Cash App, Zelle, and Apple Pay are meant to send one-time payments to family and friends. They aren’t designed to streamline group trip payment processes.
Between the money apps and using one too many spreadsheets to track all payments, a manual payment system can get hectic and lead to costly mistakes like forgotten payments, incorrect amounts, and even currency issues.
Buoyant uses an automatic group payment solution designed for group travel to collect deposits, manage payment plans, and send automated payment reminders. No chasing your people or forgetting to send a reminder.
Tired of chasing payments already? See how Buoyant automates the entire process ↓
Reason #4: 20+ Hours of Research that Leads to Tourist Traps
The Time Cost of DIY Trip Planning
DIY trip planning can be fun, but it’s no secret that group trip research is timely. On average, travelers spend 20+ hours researching before a trip—a full-time job on top of everyday life. Group travel likely takes longer because there are more people and variables to consider.
Booking a flight or hotel is one thing, but what about the decision fatigue of reading dozens of restaurant and tour reviews? The endless social media hunt to piece together conflicting information is tiring, too, and can lead to feeling exhausted, leading up to a trip instead of energized, which your entire group deserves.
How Tourist Traps Game Search Results
Spending 30+ hours researching a group trip can be frustrating, only to end up at disappointing tourist traps once your group arrives. Travel experts know how to spot fake reviews, where to find authentic group activities, and how to interpret the fine print to help you avoid lackluster tourist traps.
Reason #5: Hidden Fees Destroy Your Carefully Planned Budget
The Fine Print You'll Miss
Cleaning fees, resort fees, service charges, and strict cancellation policies are often difficult to find or understand. Companies bury this information, which can easily add hundreds to any trip.
When a travel expert plans your group trip, their trained eyes know what questions to ask the hotel and tour providers to uncover the hidden travel fees before booking.
How Extra Costs Add Up Fast
Those extra costs add up fast, and while sometimes they can’t be avoided (like hotel incidental fees), they should always be fully understood and explained to the group before any bookings are made or contracts are signed.
You don’t want your group to think something is priced lower and then, upon arrival, everyone finds out another unexpected charge is due, and they have to come out of pocket at the last minute.
The Savvy Alternative to DIY Group Trip Planning
What Professional Group Travel Planning Actually Includes
When using professional group travel services, you can offload the stress that DIY group trip planning can bring onto an expert who has streamlined automatic payments, knows the right questions to ask your group and travel providers to curate the best experiences, and has insider access that only travel planners do.
How Buoyant Eliminates These 5 Problems
At Buoyant, we’ve been curating global group trips since 2019. Our travel experts create stress-free group trips for birthdays, bachelor and bachelorette parties, graduations, team retreats, and other milestone celebrations.
We use automatic payments, deep destination insight, and fine-print understanding to connect groups with the coolest people, places, and experiences worldwide.
We know photographers in Accra, Ghana, surfers in Dakar, Senegal, DJs in London, chefs in Salvador de Bahia, and so much more that we share with our custom group trip clients.
Ready to Skip the Group Chat DIY Planning?
Your Kinfolk Deserve Better Than DIY Stress
Are you ready to skip the group chat chaos and payment chasing? Since 2019, dozens of groups have trusted Buoyant to handle the stress so they can focus on the memories.
Start planning your stress-free group trip now
