13 Things Travelers Always Overestimate When Planning a Trip
There’s a version of you that exists only in the trip-planning phase. This version wakes up at dawn for golden hour photos, reads three novels by the pool, hits the hotel gym every morning, and somehow visits twelve museums in a single afternoon.
This version of you is a lie. Oh well, maybe Eileen Gu would pull it off, but not us, the average individual.
We know this because a viral Reddit thread asked travelers to confess what they always overestimate when planning a trip, and the responses were painfully, hilariously relatable. Here’s what came up again and again.
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1. How Many Books You’ll Read
The number one culprit. Travelers consistently pack two, three, sometimes an entire tote bag of books (I am guilty of that), convinced that planes and hotel rooms will transform them into voracious readers.
In reality? You flip through 40 pages on the flight, fall asleep, and the books spend the rest of the trip quietly judging you from the nightstand.
The e-reader crowd has largely solved this problem, though a worthy counter-strategy emerged in the thread: bring two books, and make visiting a local bookstore part of the trip itself.
- Our fastest Kindle Paperwhite ever – The…
- Ready for travel – The ultra-thin design has a…
- Escape into your books – Your Kindle doesn’t…
- Battery life for your longest novel – A single…
- Read in any light – Adjust the display from…
2. How Much Clothing You’ll Need
A close second and perhaps the most universal overpacking sin. Ten shirts for a long weekend. Fifteen pairs of underwear for five days. Three “just in case” jacket options. Sound familiar? Don’t lie to yourself. To me, it does sound very familiar, and I have been on the road for the past 8 years.
The dirty secret is that most people wear the same two or three outfits on rotation anyway, and laundry, either by hand in the sink or at a local laundromat, is almost always an option.
The golden rule many seasoned travelers swear by: pack, then remove half.
3. Your Energy on Day One
You land, drop your bags, and picture yourself heading out to explore right away. In reality, you sit down “for just five minutes,” open your phone, and suddenly it’s 9 PM.
Between jet lag, the stress of getting there, heat, hauling luggage, and just figuring out the area, the first day almost always delivers far less mileage, literal and figurative, than you planned for.
Well, I used to do that before, but now I give myself grace on arrival day. It’s not laziness, it’s kindness towards my body.
4. How Much You Can Pack Into a Single Day
Itinerary planning on a laptop, with a coffee, in the comfort of your home, makes everything look deceptively close and doable. The map lies. A “quick” walk between two sights ignores hills, heat, cobblestones, a spontaneous gelato stop, and the fact that you’ve already done 14,000 steps.
Factor in meals, transit, bathroom lines, and the occasional getting-lost moment, and most travelers find they comfortably hit half their planned list, and that’s on a good day.
5. How Much Time You’ll Spend at the Airport
The classic overcorrection. Haunted by the fear of missing a flight, many travelers arrive so early they end up sitting at the gate for hours, nursing an overpriced airport coffee and rereading the same departure board. To be fair, most of the thread agreed: arriving too early beats missing your flight by a mile.
And for a certain type of traveler, like myself, there’s genuine joy in a slow airport morning. I usually get there 3-4 hours early, so I am the first to check in and get to the boarding gate on time, avoiding the bag check line.
Then I am ready to sip my coffee and finally indulge in an almond croissant while working from my laptop. It’s one of my favorite things to do in life. And yes, you can call me weird.😬
6. How Likely You Are to Work Out
You pack the gym shoes. You look up whether the hotel has a fitness center. You mentally schedule a morning run along the waterfront. And then… You don’t. Because you’re on vacation.
Because your legs are tired from walking all day. Because the hotel breakfast starts at 7:30, and why would you waste that?
Gym gear is one of the most reliably unused items in any traveler’s suitcase, and yet we keep packing it, optimistic to the last.
Full disclosure: I’m not saying you should ditch the gym. But if you consistently get your workouts in, daily or weekly, that already matters.
I know it takes discipline and willpower. I only found mine when I stopped focusing on how I looked and started focusing on how I felt, and on managing menopause-related issues.
Now I move every day. Not always with the same intensity, but I show up, and that’s what makes the difference.-related pathologies. So now I do exercise every day even if not with the same intensity. Obviously, if I know that I am going to be walking 20K steps while exploring a city, I limit the workout to only some weightlifting and abs (I use resistance bands)
- 100% Natural Latex
- Package Included: 5 pull up bands, 1 carrying bag…
- Durable Natural Odorless: Pull up bands are made…
- Versatile 5-piece fitness bands: Ideal for all…
- Boost Your Strength: We recommend that athletes…
7. How Much Cash You’ll Need
The world has gone increasingly cashless, but many travelers still convert a stack of local currency out of habit or anxiety, only to bring most of it back home. One commenter spent an entire week in the UK and barely touched their £100.
That said, it’s destination-dependent. Germany came up as a notable exception where cash is still very much king. In Mexico, you still find many places that don’t accept cards.
The lesson isn’t to skip cash entirely, but to research your destination and resist the urge to over-convert.
8. How Many Restaurants Can You Fit In
You built a list. You cross-referenced it with three food blogs and two Reddit threads. You have a spreadsheet. And then you find that perfect little spot on night two, and you go back. And back again.
One great restaurant has a way of quietly displacing five others on your list — and honestly, that’s not a bad thing. Over-scheduling meals is one of the most common ways to turn eating (one of travel’s great joys) into a stressful to-do list.
Unless you need to check out all the restaurants in a destination for business purposes, you can stick to your favorite one without any guilt towards your Instagram followers. 😜
9. How Many Sunrise or Early Morning Moments You’ll Actually Catch
“I’ll wake up at 5:30 for the sunrise over the ruins.” Sure you will. After a day of walking, a nice dinner, and staying out later than planned, that alarm at 5:30 AM hits very differently than it did when you penciled it into your itinerary at home.
Golden hour photos are magical. Sleep is also magical. Most travelers, it turns out, are Team Sleep more often than they’d like to admit. And that’s ok. It’s your vacation, your time, your life.
10. How Many Snacks Do You Need to Pack
Lovingly assembled trail mix, an emergency Ziploc of granola bars, and a bag of chips that will inevitably explode at altitude, travel snacks are packed with the best intentions. The reality is that other countries have snacks too, and you’re usually too busy exploring to remember you have any. The snacks come home largely intact, or get eaten at the airport on the way back in a fit of boredom.
11. How Many Toiletries and Medications You’ll Need
The “what if” toiletry pouch is a real phenomenon. Pepto-Bismol, antifungal cream, three types of pain reliever, and a backup of the backup sunscreen. All packed because hunting down a pharmacy abroad feels daunting, even though pharmacies exist in every country on earth. A reasonable emergency kit is smart. A pouch that weighs more than your shoes is probably overkill.
Having said that, if you are taking any specific medicines, like my must-take homeopathic remedies, you should definitely pack them and carry them in your handbag. God forbids you leave them behind or, even worse, lose them.
12. How Many Camera Lenses You will Actually Use
For the photography-minded traveler, this one stings. You pack three lenses “for different situations.” You use one. The other two live in your camera bag, adding weight, adding bulk, and slowly destroying your back and neck over the course of a week. Most seasoned travel photographers will tell you: pick your one workhorse lens and leave the rest at home.
I don’t have a home base, so I need to carry everything with me, and that is why I only have 2 lenses and a drone, and that’s heavy enough. But on my daily walks and explorations, I carefully choose what to bring with me.
13. How Much Your Phone Will Need Charging
The giant power bank, the backup power bank, the collection of charging cables, we travel like our phones are running a cryptocurrency mining operation.
In practice, most travelers find their phone holds up fine through a normal day of maps, photos, and the occasional story upload. A mid-sized power bank is usually more than enough.
And you can carry your phone charger and recharge it when you stop for lunch or coffee.
The industrial-grade battery pack can probably stay at home.
The Takeaway
The gap between planning you and traveling you is wide, and it’s mostly a good thing. It means you’re spontaneous. It means you’re willing to slow down. It means you found a restaurant worth going back to, slept in instead of chasing a sunrise, and didn’t need four changes of clothes after all.
The best trips aren’t the ones where you executed the plan perfectly. They’re the ones where you were present enough to let the plan fall apart in the right ways.
Pack less and read fewer books, or get an e-reader!
