Many years ago, when I first made the transition to the hospitality industry, I quickly learned something surprising: a significant number of people have tremendous anxiety when it comes to trip planning. From our own friends, we would often hear reactions like this:
It was disheartening to hear people being so stressed out about their overseas trip plans. Of course, planning a trip should be fun. Maybe you’re dreaming about that perfect meal in Kyoto, watching the sun rise over the pyramids of Giza, or finally seeing the Mt Everest in person. But somewhere between opening too many browser tabs and trying to decode train schedules in a foreign language… the joy can quickly transform into stress.
So why does trip planning suck for some people? Having heard the feedback from thousands of our guests over the years, here are some of the common friction points we’ve compiled along with our own suggested solutions:
Too Many Choices, Not Enough Time
There are countless blogs, videos, and reviews for many destinations. Some, like Japan or Italy, have a firehose of info and a dizzying amount of conflicting feedback. You might want to do the best things, not just the popular ones, but suddenly, you find yourself comparing four different day trips, five hotel options, and wondering if you should cancel it all and just stay home.
Suggestions:
Try to keep in mind that most places don’t need to be overplanned. Also (it’s quaint to say this in the modern world) word of mouth advice from trusted friends is still one of our most reliable resources in the travel world. There are a lot of great resources on social media, but they’re not relevant if the person giving advice does not understand your taste and style. The opinion of a random person on the internet could very far from your own.
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!
Information Overload
Is the must-try restaurant open on Tuesdays? Does it match the museum schedule on that side of town? Do we need a reservation for that shrine? Is the national park closed during holidays? How many train connections will we need? How do we avoid the crowds? What do we do with our suitcases? Welcome to the rabbit hole of logistics. You don’t always need to plan every single detail, but for those who start, it quickly escalates into when, how, for how long, and with what backup plan if it rains.
You started with wanderlust, but now you’re working 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, confusion, and misinformation. Even details like seasonality can make a significant difference; just because something was true in March, the same might not apply in April. 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.
Most importantly, don’t overplan. Make sure to keep yourself flexible and give yourself room to discover things on accident. It’s ok to simply walk into a random restaurant blindly and trying it out! Even for us, where our responsibility is to plan every single detail on our tours, we know and appreciate that some of the best travel experiences are the ones that we have on accident.
Go from FOMO (Fear of Missing Out) to JOMO (Joy of Missing Out)!
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? For a lot of travelers, these worries become real pressures.
When it comes to FOMO, 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 when traveling, we risk missing the whole point of the journey. Overloading itineraries leads to stress and fatigue, overshadowing the joy of exploration. Instead of creating cherished memories, we might find ourselves just remembering how tiring a trip was. 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.
Another thing that helps to deal with FOMO is to remember to focus on what actually makes you happy instead of what everyone else is doing. A great first step is practicing “JOMO,” or the Joy Of Missing Out, where you intentionally enjoy being present in your own life without the noise.
“Anything works for me” is code for: “You choose. I’ll judge.”
Travel with a group of friends and family is precious. However, 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 absolutely 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 unofficially responsible 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 that’s 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?
- Do we all have the same travel goals (probably not)? If not, plan time to be apart from each other.
- Do we need to build in independent time to have more space apart?
It’s a Full-Time Job
Unless your real job is travel planning, you’re probably squeezing all the the trip planning into evenings, weekends, and stolen lunch breaks. That vacation you’re dreaming of starts to feel like work.
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?
We won’t pretend to have all the answers. What we DO hope to accomplish is to remind you of common pain points. By identifying them, we hope you can prepare for them and address the normal friction that people hit with trip planning.
Trip planning isn’t rocket science, and travel itself is the awesome part! What can suck is the time, insider knowledge, and obsessive attention to detail it takes to do trip planning well. If the tips above still aren’t enough, that’s where an expert can make a meaningful difference.
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.” That’s funny to us because we aren’t tour people either! BUT, once our travelers 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 so you can focus your energy on enjoying the actual trip.
Finding the right trip planner is like finding a housepainter. Sure, you could do it yourself. If you’ve got the time, energy, and a bit of experience, it will turn out great! But if you don’t want to spend your weekends taping trim and shopping for primer, brushes, and rollers, hiring a trusted professional will make all the difference for a great result.
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 😊
