Choosing a low-cost airline. Booking a poor accommodation. Traveling with unsuitable companions.

Reflecting on vacation regret is common, especially as the summer of 2024 comes to an end. In fact, many people may find they have regrets.

Personally, I faced my own issues. I didn’t prepare beforehand and ended up paying way too much for my flight. ($630 for a one-way ticket from Berlin to Stockholm? Seriously, SAS!) I wish I had spent more time in Europe, despite the overcrowding. Instead of complaining, I should have enjoyed more German bread.

“Americans have very limited vacation time,” noted Kimberly Davis, a travel advisor. “This summer, there seems to be a lot of regret.”

Consider subscribing to Elliott Confidential, the travel newsletter they prefer you don’t see. Inside, you’ll find crucial updates, thorough insights, and unique tips for improving your travel experiences. But keep it under wraps!

The most frequent regret comes from rushing through a “must-do” checklist during the summer, driven by fear of missing out on experiences. Ironically, this rush leads to missing out on everything as you’re just checking off items, according to Davis.

As summer wraps up, it’s time to assess our vacation regrets. Future trips like the upcoming holiday season, spring break, and summer of 2025 are on the horizon – and you certainly don’t want to repeat the same mistakes!

So, what kinds of regrets are common? They generally fall into three main categories.

Travelers regret choosing the wrong airline, cruise line, or hotel

Some issues are unforeseeable. For instance, not many could have predicted the Delta Air Lines breakdown due to a major CrowdStrike software failure. Still, some mishaps are avoidable. For those who opted for the cheapest flights or hotels, it’s likely they faced preventable problems.

Alex Wong, a consultant and writer, booked a flight with a budget airline that offered nearly no customer support. His travel from Shanghai to Seoul got canceled due to severe weather, and the airline went completely silent.

“It was just endless agony waiting around,” he remembered. At one moment, frustrated passengers started gathering at the gate, shouting at the overwhelmed agent. Wong learned a crucial lesson – avoid cutting costs on flights.

He’s not alone. This summer, I’ve heard numerous stories from travelers who reserved accommodations with poor customer support or zero assistance. Folks! Remember, you often get what you pay for.

Another common regret: lack of planning

Due to the limited time available, many individuals attempted to create overly ambitious itineraries, leaving little margin for error.

“Without a doubt, the biggest regret among my clients this summer was not allowing enough time for connections on international flights,” shared Heather Herbert, a travel advisor at Heather Concierge Travel.

She mentioned instances where her clients had tight connections from domestic to international flights, and weather delays caused significant issues.

“In one example, a frantic dash to the international terminal led to the cabin door being closed. Fortunately, the captain ultimately showed mercy and reopened the door,” she recounted.

Another related disappointment is overloading your schedule with activities, leaving you unable to truly appreciate any of them. I became so exhausted from hopping from one appointment to the next that I started limiting my plans to just one activity per day. That’s right, one – ideally in the morning, leaving me the rest of the day to explore the area at my own pace.

The greatest regret of all

However, there’s one overarching vacation regret that surpasses all others: the missed opportunity.

Andrew Harper was researching an article on the finest wine bars in Venice when he came across the famed Cantina do Mori.

“Caught between stopping for a glass of wine or sticking to my plan to visit galleries, I opted to postpone my stop – only to find it closed and reopening after I had left,” said Harper, an editor at the Hideaway Report. “It served as a valuable reminder to leave space in your itinerary for unexpected discoveries.”

How many summers do you have left?

In my early days as a consumer advocate, I encountered many individuals who had dedicated their lives to work

Many people save for exciting trips in their retirement, dreaming of cruises or safaris, only to face serious health issues that prevent them from traveling (which is why travel insurance is essential). Eventually, they may come to terms with the fact that their travel plans will remain unfulfilled.

“The greatest regret is not going on vacation while you have the chance, good health, ability to move, and free time,” stated Mitch Krayton, a travel advisor based in Aurora, Colorado.

Barriers can accumulate quickly—whether it’s a bad back, poor currency exchange rates, or mobility issues. I experienced something similar when I broke my pelvis in two places during a trip to Switzerland; I often wished to be home enjoying warm drinks. But instead, I took a few weeks to rest in Barcelona and then traveled to Antarctica.

Krayton is correct; you only have one life to live.

You will likely regret not taking a trip more than those you do take. As you age, these regrets tend to accumulate until you find yourself at the end of your life, facing a long list of missed travel opportunities. Don’t let that become your reality.

Elliott’s advice for avoiding travel regrets

It’s crucial to make wise vacation choices; you don’t have to go through painful experiences or bad news to avoid poor vacation decisions. Here are some tips to ensure your getaway is regret-free:

• Seek professional advice. Issues like over-scheduling, choosing the wrong airline, or overlooking major attractions can be avoided with the help of an expert. Before planning your next trip, consider consulting a travel advisor, coach, or a well-traveled friend.
• Travel with loved ones. Make sure those you wish to accompany you genuinely want to travel. There’s no joy in dragging your grandchildren to a museum in Milan if they would prefer a fun-filled day at a theme park in Orlando. (I can speak from experience—it’s not a great idea.)
• Don’t delay. Stop postponing your travel plans and just go. Rarely will you find someone who regretted taking a trip, but many wish they had traveled more.

The most effective way to overcome travel regrets is to plan a revisit. In just a few months, the planning season for next summer’s vacations will commence—why not start now?