About halfway through my trip to Tokyo last November, I started to have regrets.
This was my first time in the Japanese capital and knowing how huge the city is, I was feeling overwhelmed even when planning the trip. I enlisted the help of a friend familiar with Tokyo for accommodations and she recommended Shibuya, which is Tokyo’s equivalent of New York’s Times Square and home of the iconic Shibuya Crossing. Their rationale: It was convenient and located near tourist attractions.
However, after reaching there I felt stressed seeing the huge number of people. While I knew the heart of Tokyo was going to be bustling, nothing prepared me for the confusing train stations and streets so busy that walking on them was like being stuck in the middle of a crowd. I soon realized that I would prefer to live in a quiet neighborhood, especially as a solo traveler.
Although I wouldn’t call the entire trip a flop, I would do it again if the opportunity arose. For the record, I don’t blame my friend; I just wish I had done better research.
Overall, travel is transformative and enjoyable, but it can also be frustrating. After investing time and money on a vacation, it can be disappointing when it fails to meet expectations, and some travelers go home with regrets as their souvenir.
In a March 2026 survey by Travel Guard, 97% of 1022 American travelers said they regretted at least one trip. About two-thirds of survey respondents said they would take a “mulligan” and re-do their trip, while one-third would cancel it and take another trip.
“People regret trips when preventable issues derail the experience,” Rhonda Sloan, CMO of Travel Guard, told USA TODAY. “Our research shows that unexpected disruptions such as delays, illness or cancellations are a major cause, but many regrets actually stem from decisions made by travelers… from not planning properly or setting a realistic budget, traveling with the wrong companions or letting stress get the best of them.”
Why do travelers regret their trips?
The biggest source of frustration for travelers is “something went wrong during the trip,” as reported by 17%. More specifically, travelers said the most common issues were accommodation problems, arguments with travel companions, bad weather and crowded destinations.
Other frequently cited reasons included not planning the trip properly, being too stressed or overwhelmed to enjoy the vacation, and choosing the wrong travel companions.
Not all trips are the same, some types of trips cause more regrets than others. According to 27% of respondents, family vacations are most likely to end with mixed emotions, especially when with parents or extended family, which can add pressure and mismatched travel styles. Adventure trips, quick city tours, romantic trips and solo trips are other commonly regretted trips.
Experience also plays a role in how your trip will turn out.
Most travelers surveyed said their biggest regrets occurred as young adults. “We also found that the trips Americans most regret were those taken in their 20s, when travelers had less experience and smaller budgets,” Sloan said. “The good news is that with better planning, thoughtful choices, and the right travel insurance plan, many of those regrets can be avoided.”
lessons learned
Thankfully, all is not lost when a trip doesn’t go perfectly. Nearly three-quarters of travelers said they learned from their mistakes, and those experiences influence how they plan trips.
Meredith and Colby Thomas’ recent trip to Cuzco, Peru did just that. In early May, the full-time travel blogger was flying in from Mexico and had an hour and a half layover in Lima before reaching Cuzco. The connection seemed tight, but since the flight was booked on the same ticket on the same airline, they figured it would work out.
He almost missed his flight.
They encountered minor delays in boarding and disembarking in Lima before reaching the long customs line. The couple had been waiting for 45 minutes when their flight to Cusco took off. At the final boarding call, he begged a customs officer to let him go forward – and took off just as the doors were closing.
“We were stressed out of our minds and rushed to our gate at the last minute — definitely not the way you want to start a trip,” said Meredith Thomas, who co-runs the travel blog Two Packs and a Pup.
The couple regret booking that flight, and now make sure they have enough time for their stay.
A nervous travel day didn’t derail Thomas’ trip to Peru, although he got off to a rough start. Meredith Thomas said, “You have to expect an element of uncertainty with travel and be prepared to go with the flow, but when things go so far off track, it’s natural to have some carryover stress and exhaustion the next day.”
I took the same approach to that trip to Tokyo, doing my best to embrace the bright lights and high energy of Shibuya while I was there, even if it wasn’t ideal. When I return I will know what to do.
