Travelers Regret a Trip. Did You Make These Mistakes?

A March 2026 Travel Guard survey of 1,022 U.S. travelers found that 97% regret at least one trip, with about two-thirds saying they would redo it and one-third would scrap it altogether. The author shares a personal Tokyo experience illustrating the kinds of misjudgments and overwhelm that can sap enjoyment. Respondents cited preventable disruptions such as delays, illness or cancellations as major triggers, but many regrets stem from planning missteps and budgeting choices. The biggest single disappointment was that something went wrong during the trip, cited by 17% of respondents. Family holidays were the most regretted category, at 27%. Travel Guard’s Rhonda Sloan says travelers regret often because of choices like poor planning, excessive stress or the wrong travel companions. The survey also highlights regret patterns by trip type, with adventure travel, quick city visits, romantic getaways and solo trips commonly mentioned. Researchers emphasize that better preparation, realistic budgeting and flexible expectations can reduce disappointment.