Summer’s over: What are your top vacation regrets?

Flying a budget airline. Staying at a bad hotel. Traveling with the wrong people.
You may have a few vacation regrets for the summer of 2024. More than a few, actually.
I do. I didn’t plan in advance and I way overpaid for my airfare. ($630 for a one-way ticket from Berlin to Stockholm? Come on, SAS!) I should have spent more time in Europe, even though it was overcrowded. I should have complained less and eaten more German bread.
“Americans get so little vacation time,” says Kimberly Davis, a travel advisor. “But this summer, they have so many regrets.”
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The most common one is the result of reflexively running through a “must do” list during the summer because you’re afraid of missing out on something. And in the process, you miss out on everything, “because you’re just running through a list,” says Davis.
Now, with summer ending, it’s a good time to take inventory of all our vacation regrets. Because there are future trips to plan: the upcoming holiday travel season, spring break and the summer of 2025. You don’t want to repeat any of these errors, right?
But what are these regrets? They fit neatly into three categories.
Sometimes, you can’t know what will happen. For example, who could have known about the Delta Air Lines meltdown after the massive CrowdStrike software glitch? But some disasters are predictable. All those people trying to save a little money by choosing the cheapest flights or hotels? Yeah, those were probably preventable.
Alex Wong, a consultant and writer, booked a ticket on a budget carrier that had zero customer service. His flight from Shanghai to Seoul was canceled because of bad weather, and the airline simply went silent.
“It was just endless torture waiting around,” he recalls. At one point, passengers started crowding around the gate, and they began screaming at the hapless agent. Wong says he learned an important lesson: Don’t cut corners when you’re flying.
He’s hardly alone. This summer, I’ve heard from countless travelers who reserved a room at a hotel with horrible customer service or a vacation rental with none at all. People! You get what you pay for.
Because time is at such a premium, many people tried to plan ambitious itineraries that left little room for error.
“Absolutely the No. 1 regret my clients are having this summer is not allowing extra time with connections on international flights,” says Heather Herbert, a travel advisor with Heather Concierge Travel.
She says in two of the cases, her client had a close connection from a domestic airport for an international flight, and weather delays resulted in problems.
“In one case, a mad sprint to the international terminal resulted in finding the cabin door closed. The captain, ultimately, did reopen the door in an act of great mercy,” she recalls.
Here’s a related regret: Stuffing your itinerary with so many activities that you can’t enjoy any of them. I got so tired of running from one appointment to another that I’ve started limiting my activities to just one per day. That’s right, one activity — preferably in the morning — and then the rest of the day to explore the destination on my own.
But there’s one vacation regret that towers over all of the others, and it’s the missed opportunity.
Andrew Harper was working on a story about the best wine bars in Venice when he stumbled upon the legendary Cantina do Mori.
“Torn between stopping for a glass of wine and continuing on with my plan of gallery-hopping, I decided to return later, only to find that it was closed and wouldn’t reopen until after I flew home,” says Harper, who edits the Hideaway Report. “It was a good reminder to leave room in an itinerary for serendipitous discoveries.”
When I started my career as a consumer advocate, I met many readers who had spent their entire lives working and saving up to travel after they retired. Then they booked a dream cruise or a safari, only to suffer a debilitating illness just before leaving (that’s why there’s travel insurance). And then they realized they would never travel.
“The biggest regret is not taking a vacation while you have the opportunity, health, mobility and time,” says Mitch Krayton, a professional travel advisor in Aurora, Colo.
It doesn’t take long for the barriers to pile up: a bad back, an unfavorable exchange rate, trouble getting around. I know what that feels like. I broke my pelvis in two places a few years ago in Switzerland, and a part of me just wanted to be at home sipping hot chocolate. Instead, I rested for a few weeks in Barcelona and then flew to the Antarctic.
Krayton is right; you only live once.
I guarantee you’ll regret the trip not taken. And the older you get, the more those regrets pile up until you are at the end of your life and you have a long list of trips not taken. Don’t let that be your regret.
You don’t have to break any bones or get a serious health care diagnosis to avoid a bad vacation decision. Here are some strategies for avoiding a regrets-free getaway:
Get professional help. Problems like overplanning, booking the wrong airline or missing an important attraction are avoidable with the guidance of a pro. Consult a travel advisor, travel coach or a well-traveled friend before you start planning your next vacation.
Travel with the ones you love. But make sure the ones you love want to travel. There’s absolutely no point in dragging your grandkids on a museum tour of Milan if they’d rather go to the Magic Kingdom in Orlando. (Believe me, I’ve done this. It’s a recipe for disaster.)
Don’t wait. Stop putting off your vacation and go. I can’t remember the last time I met someone who regretted traveling. But I’ve met plenty of people who were sorry they didn’t travel.
The best way to handle vacation regret is a do-over. In just a few months, planning season starts for next summer’s vacations, so why not get started now?
Christopher Elliott is an author, consumer advocate, and journalist. He founded Elliott Advocacy, a nonprofit organization that helps solve consumer problems. He publishes Elliott Confidential, a travel newsletter, and the Elliott Report, a news site about customer service. If you need help with a consumer problem, you can reach him here or email him at [email protected].