When I first made the transition to the hospitality industry, I quickly learned something surprising. 99% of people have tremendous anxiety when it comes to trip planning.
It was disheartening to hear people around me being so stressed out about their overseas trip plans. Of course, planning a trip should be fun. You’re dreaming about that perfect meal in Kyoto, watching the sun rise over the Sahara, or finally seeing the Eiffel Tower in person. But somewhere between opening too many browser tabs and trying to decode train schedules in a foreign language… the joy fades. Fast.
So why does trip planning suck? Having heard the feedback from thousands of our guests over the years, here are some of the common friction points we’ve compiled and some suggested solutions:
1. Too Many Choices, Not Enough Time
There are countless blogs, videos, and reviews for every destination. You want to do the best things, not just the popular ones. Suddenly though, you find yourself comparing four different day trips, five hotel options, and wondering if you should cancel it all and just stay home.
It’s not freedom, it’s fatigue.
Suggestions: It’s funny to say this in our modern digital world, but word of mouth advice from friends is probably still our most reliable source in the travel world. If you have any friends/family who have recently done similar trips, don’t be shy about getting their thoughts! Otherwise, if you don’t know anyone personally, try to see if you can find the assistance of a professional. In our case, we’re always happy to share our experience and knowledge!
2. Information Overload
What’s open on Tuesdays? Do you need a reservation for that shrine? Is this museum closed during national holidays? How many train connections will we need? What do we do with our suitcases? Welcome to the rabbit hole of logistics. It’s not just “where to go”—it’s when, how, for how long, and with what backup plan if it rains.
You started with wanderlust. Now you’re building a spreadsheet.
Suggestions: If you’re feeling overwhelmed, stay off social media. Instagram, tiktok, and other platforms are great tools for some things, but when it comes to travel, they can also be the biggest sources of unrealistic expectations and misinformation. When it comes time to plan, if you happen to know someone in-destination, make sure to get in touch with them for their advice. Things around the world always change quickly and local knowledge will almost always be better and fresher than information online.
3. The Fear of Missing Out (FOMO)
When you’re planning your own trip, every decision feels final. You worry: Did I miss something better? Should I have stayed an extra day there? Is this restaurant too touristy?
There’s no undo button for a missed memory. That pressure? It’s real.
When it comes to giving in to FOMO however, the thing everyone always forgets is the exhaustion you’re exposing yourself to. In fact, when we were starting out, we ran into this problem constantly when designing our early tours. We always wanted to throw in as many features into an itinerary as we could. Very quickly though, we were reminded how important it is to have balance and rest, so it was decided early on that proper balance and pacing would be important design guidelines for ourselves.
When we do too much at once when traveling, we risk missing the very essence of the journey. Overloading itineraries leads to stress and fatigue, overshadowing the joy of exploration. Instead of creating cherished memories, we might find ourselves recalling only the exhaustion. To us, that would be the worst outcome of all.
Suggestions: Just like with food, it’s normal for “our eyes to be bigger than our stomachs” when it comes to travel. To help reduce the FOMO, keep in mind that if a destination is really worthwhile, you will likely be going back. For example, the most common mistake people make when planning a trip to Japan is cramming FAR too much into their schedules because they think of it as a once-in-a-lifetime type of trip. However, the reality is that Japan has become far more accessible for a lot of people nowadays and it’s often a repeat destination for many travelers. This means you don’t have to worry about doing everything all in one go.
4. Coordinating With Others Is a Nightmare
Let’s not forget the group chat chaos. One person wants nature, another wants shopping. Someone hates early mornings. Someone else wants to “go with the flow” (translation: they’ve done zero research). Once you get on the ground, you realize everyone has a different pace or maybe personalities don’t match as thought as well everyone thought.
You’re now the unofficial travel agent for everyone—and no one appreciates how hard it is.
Suggestions: Choosing travel companion(s) is one of the hardest, yet underappreciated things in life. There’s no right or wrong answer, especially because it will depend on so many factors (distance, length of trip, how exotic the destination is), but it is a good idea to put some thought into it in advance with questions such as
- Do we enjoy the same pace (If not, you can build more flexibility into your plans)?
- Is our destination one which is very flexible or does everything need to be booked in advance?
- Can we book some set items such as local tours to do more of the heavy lifting?
5. It’s a Full-Time Job
Unless your real job is travel planning, there’s a good chance you’re squeezing this into evenings, weekends, and stolen lunch breaks. That dreamy vacation starts to feel like work before the actual work of packing.
Suggestions: Don’t underestimate the time cost of travel planning. For a more laid-back planning experience, it’s always a good idea to start sketching out ideas early. How far in advance will differ depending on how exotic your trip plans are, but in general, 6-9 months ahead is a good timeframe for most international trips. Some high-demand or exotic destinations (African Safari, Galapagos Islands, etc) should be planned 12 months ahead.
So… What’s the Answer?
Trip planning doesn’t suck because travel isn’t amazing – it can suck because the desire of doing it well takes serious time, insider knowledge, and a borderline obsessive attention to detail; often more than we expect. Everyone’s situation is different, so if the suggestions listed above don’t work for you, that’s where the help of an expert can be a significant improvement.
For us, designing thoughtful, ready-to-go travel experiences is all we think about. We take care of the logistics, timing, reservations, and all the “what ifs,” so you can focus on the joy of being in the moment.
We often hear from guests who say, “I’m not a tour person.” We get it—neither are we in the traditional sense. But once they experience what a well-designed, well-paced tour can be, it completely shifts their mindset. It’s not about following a flag around—it’s about removing the stress while keeping all the magic.
Here’s the analogy I always like to think of when it comes to finding the right trip planner:
Planning a trip is like painting your house. Sure, you could do it yourself. If you’ve got the time, energy, and a bit of experience, it could turn out great! But if you don’t want to spend your weekends taping trim and shopping for primer, hiring a professional can make all the difference.
Trip planning is similar. If you’ve ever found yourself wondering “is there someone out there that I can trust with this important job??” the answer is YES! When you find an expert you trust, you still get the adventure, the stories, the “wow” moments. We simply take the guesswork (and late-night group texts, restaurant reservations, + train transfers) off your plate.
In other words, you don’t need to be a travel expert to have an incredible trip. You just need to know one 😊
